CID 5282108 alpha-IONONE

Structures Structure depictions of this compound, including computationally generated two-dimensional (2D) and three-dimensional (3D) structures, as well as experimentally determined 3D single-crystal structures.

2D Structure A two-dimensional (2D) structure representation of the compound. Because this structure is processed through chemical structure standardization (Hähnke et al., J. Cheminform. 2018, 10, 36), it is not necessarily the same as the structures provided by individual data contributors. https://doi.org/10.1186/s13321-018-0293-8 true 75 true

3D Conformer A three-dimensional (3D) structure representation of the compound. This 3D structure is not experimentally determined, but computed by PubChem. This structure may or may not be the same as the inherent structure of the compound you would expect to see in vacuum or in the gas phase, because the underlying computational algorithm aims to generate a protein-bound structure, which would be observed in a protein-ligand complex. More detailed information on this conformer model can be found in Kim et al., J. Cheminform. 2013, 5, 1. https://doi.org/10.1186/1758-2946-5-1 true 75 alpha-IONONE 5282108

Chemical Safety Link to the Safety and Hazard section of this page and link to the Laboratory Chemical Safety Summary (LCSS) datasheet for this compound. true true 75 Chemical Safety 0 1 https://pubchem.ncbi.nlm.nih.gov/images/ghs/GHS07.svg Icon Irritant

Names and Identifiers Chemical names, synonyms, identifiers, and descriptors.

Record Description Summary Information true true 2 Record Description Ontology Summary Alpha-ionone is an ionone, an enone and a methyl ketone. 0 12 https://pubchem.ncbi.nlm.nih.gov/compound/Alpha-ionone PubChem Internal Link CID-5282108 42 13 https://pubchem.ncbi.nlm.nih.gov/compound/methyl%20ketone PubChem Internal Link CID-180 38 alpha-Ionone is a natural product found in Camellia sinensis, Leonurus japonicus, and other organisms with data available. 43 17 https://pubchem.ncbi.nlm.nih.gov/taxonomy/4442#section=Natural-Products 62 18 https://pubchem.ncbi.nlm.nih.gov/taxonomy/4138#section=Natural-Products 86 15 #section=Taxonomy 0 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-Ionone PubChem Internal Link CID-5282108 72 alpha-Ionone belongs to the family of Monocyclic Monoterpenes. These are monoterpenes containing 1 ring in the isoprene chain 0 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-Ionone PubChem Internal Link CID-5282108 111 8 https://pubchem.ncbi.nlm.nih.gov/compound/isoprene PubChem Internal Link CID-6557 75 See Also See also: Calendula Officinalis Flower (part of). 10 28 https://pubchem.ncbi.nlm.nih.gov/compound/Calendula%20Officinalis%20Flower

Computed Descriptors Structural descriptors generated or computed for the structures of this compound, including the IUPAC name, InChI/InChIKey, and canonical/isomeric SMILES.

IUPAC Name Chemical name of this compound, computed from its structure based on the International Union of Pure and Applied Chemistry (IUPAC) nomenclature standards. https://iupac.org/what-we-do/nomenclature/ 75 Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14) (E)-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one 1 1 Italics

InChI The International Chemical Identifier (InChI) is a computed, non-proprietary identifier for a chemical structure. The InChI is an International Union of Pure and Applied Chemistry (IUPAC) standard. https://iupac.org/who-we-are/divisions/division-details/inchi/ 75 Computed by InChI 1.0.6 (PubChem release 2021.10.14) InChI=1S/C13H20O/c1-10-6-5-9-13(3,4)12(10)8-7-11(2)14/h6-8,12H,5,9H2,1-4H3/b8-7+

InChIKey An InChIKey is a 27-character hash code derived from an InChI. The International Chemical Identifier (InChI) is a computed, non-proprietary identifier for a chemical structure. The InChI is an International Union of Pure and Applied Chemistry (IUPAC) standard. https://iupac.org/who-we-are/divisions/division-details/inchi/ 75 Computed by InChI 1.0.6 (PubChem release 2021.10.14) UZFLPKAIBPNNCA-BQYQJAHWSA-N

Canonical SMILES The Simplified Molecular-Input Line-Entry System (SMILES) is a widely-used line notation for chemical structures. PubChem computes two kinds of SMILES strings for compounds: canonical SMILES (computed from chemical structures devoid of isotopic and stereochemical information), and isomeric SMILES (computed from chemical structures containing isotopic and stereochemical information). This section shows the canonical SMILES of the compound. https://www.daylight.com/dayhtml/doc/theory/theory.smiles.html 75 Computed by OEChem 2.3.0 (PubChem release 2021.10.14) CC1=CCCC(C1C=CC(=O)C)(C)C

Isomeric SMILES The Simplified Molecular-Input Line-Entry System (SMILES) is a widely-used line notation for chemical structures. PubChem computes two kinds of SMILES strings for compounds: canonical SMILES (computed from chemical structures devoid of isotopic and stereochemical information), and isomeric SMILES (computed from chemical structures containing isotopic and stereochemical information). This section shows the Isomeric SMILES of the compound. https://www.daylight.com/dayhtml/doc/theory/theory.smiles.html 75 Computed by OEChem 2.3.0 (PubChem release 2021.10.14) CC1=CCCC(C1/C=C/C(=O)C)(C)C

Molecular Formula A chemical formula is a way of expressing information about the proportions of atoms that constitute a particular chemical compound, using a single line of chemical element symbols and numbers. PubChem uses the Hill system, whereby the number of carbon atoms in a molecule is indicated first, the number of hydrogen atoms second, and then the number of all other chemical elements in alphabetical order. When the formula contains no carbon, all the elements, including hydrogen, are listed alphabetically. Sources other than PubChem may include a variant of the formula that is more structural or natural to chemists, for example, H2SO4 for sulfuric acid, rather than the Hill version H2O4S. https://pubs.acs.org/doi/abs/10.1021/ja02046a005 true 75 Computed by PubChem 2.2 (PubChem release 2021.10.14) C13H20O

Other Identifiers Other identifiers assigned to this chemical.

CAS A CAS Registry Number (also called CAS RN or CAS Number) is a proprietary registry number assigned by the Chemical Abstracts Service (CAS) division of the American Chemical Society (ACS). It is a numeric identifier that can contain up to 10 digits, divided by hyphens into three parts. https://www.cas.org/support/documentation/chemical-substances/faqs 1 https://commonchemistry.cas.org/detail?cas_rn=127-41-3 127-41-3 4 127-41-3 5 6901-97-9 6 14398-36-8 7 31798-12-6 11 CAS 6901-97-9 13 127-41-3 14 127-41-3 15 127-41-3 18 127-41-3 19 31798-12-6 20 6901-97-9 22 127-41-3 26 127-41-3 30 127-41-3 44 127-41-3

Deprecated CAS The Chemical Abstract Service (CAS) registry numbers that are no longer used. These numbers are old, deprecated, and/or deleted, but users may still encounter them in some (old) references. 4 30685-95-1, 31798-11-5 14 30685-95-1, 31798-11-5 15 30685-95-1, 31798-11-5

European Community (EC) Number The European Community (EC) number is a seven-digit identifier assigned by the European Chemicals Agency (ECHA) to substances for regulatory purposes within the European Union. EC numbers are sometimes referred to as EINECS, ELINCS, or NLP numbers, because the EC Inventory comprises three individual inventories (EINECS, ELINCS, and the NLP list). https://echa.europa.eu/information-on-chemicals/ec-inventory 18 https://echa.europa.eu/substance-information/-/substanceinfo/100.004.402 204-841-6 19 https://echa.europa.eu/substance-information/-/substanceinfo/100.046.178 250-812-6 20 https://echa.europa.eu/substance-information/-/substanceinfo/100.027.282 230-010-2

UNII UNique Ingredient Identifier (UNII) code for this chemical. It is a non-proprietary registry number assigned by the U.S. Food and Drug Administration (FDA). https://www.fda.gov/industry/fda-data-standards-advisory-board/fdas-global-substance-registration-system 22 https://gsrs.ncats.nih.gov/ginas/app/beta/substances/I9V075M61R I9V075M61R

ChEBI ID Identifier from database and ontology of molecular entities focused on 'small' chemical compounds used by the Chemical Entities of Biological Interest (ChEBI) https://www.ebi.ac.uk/chebi/ 2 https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:32319 CHEBI:32319

ChEMBL ID ChEMBL compound identifier https://www.ebi.ac.uk/chembl/ 3 https://www.ebi.ac.uk/chembl/compound_report_card/CHEMBL472877/ CHEMBL472877

DSSTox Substance ID Substance identifier used in the Distributed Structure-Searchable Toxicity (DSSTox) Database. https://www.epa.gov/chemical-research/distributed-structure-searchable-toxicity-dsstox-database 15 https://comptox.epa.gov/dashboard/DTXSID0035160 DTXSID0035160

FEMA Number A flavor ingredient identifier from the Flavor and Extract Manufacturers Association (FEMA). See also the FEMA Flavor Profile (when available) in the Food Additives and Ingredients section. https://www.femaflavor.org/ 23 FEMA Number https://www.femaflavor.org/flavor-library/alpha-ionone 2594 35 2594

HMDB ID A chemical substance identifier from the HMDB database https://hmdb.ca/ 27 https://hmdb.ca/metabolites/HMDB0059883 HMDB0059883

JECFA Number A numeric identifier for a given food additive or flavoring agent, used by Joint FAO/WHO Expert Committee on Food Additives (JECFA). https://www.fao.org/food/food-safety-quality/scientific-advice/jecfa/jecfa-flav/online-help/en/ 35 388

KEGG ID KEGG compound/drug identifier https://www.kegg.jp/ 37 https://www.kegg.jp/entry/C12286 C12286

Metabolomics Workbench ID Registration number used by Metabolomics Workbench https://www.metabolomicsworkbench.org/ 42 https://www.metabolomicsworkbench.org/data/StructureData.php?RegNo=54536 54536

Nikkaji Number Substance identifier used in the Japan Chemical Substance Dictionary (Nikkaji). https://jglobal.jst.go.jp/en/ 31 http://jglobal.jst.go.jp/en/redirect?Nikkaji_No=J183.660I J183.660I 32 http://jglobal.jst.go.jp/en/redirect?Nikkaji_No=J2.016H J2.016H 33 http://jglobal.jst.go.jp/en/redirect?Nikkaji_No=J278.189A J278.189A

NSC Number The National Service Center (NSC) number is a numeric identifier for substances submitted to the National Cancer Institute (NCI) for testing and evaluation. It is a registration number for the Developmental Therapeutics Program (DTP) repository. https://dtp.cancer.gov/organization/dscb/compoundSubmission/faqs.htm 3 11 NSC Number https://dtp.cancer.gov/dtpstandard/servlet/dwindex?searchtype=NSC&outputformat=html&searchlist=34560 34560

RXCUI RxNorm concept unique identifier (RXCUI) https://www.nlm.nih.gov/research/umls/rxnorm/index.html 54 https://rxnav.nlm.nih.gov/id/rxnorm/1859172 1859172

Wikidata Wikidata entity identifier for the given compound. https://www.wikidata.org/w/index.php?title=Special:WhatLinksHere/Property:P662 74 https://www.wikidata.org/wiki/Q27114869 Q27114869

Synonyms Alternative names for this PubChem Compound record. A compound can have many different names. For example, acetone (CH3C(=O)CH3) is also known as propanone, propan-2-one, or dimethyl ketone. The brand name of a product is commonly used to indicate the primary chemical ingredient(s) in the product (e.g., Tylenol, a common pain killer, is often used for acetaminophen, its active ingredient). Another example of common synonyms is record identifiers used in different data collections, such as Chemical Abstract Service (CAS) registry numbers, FDA UNII (Unique Ingredient Identifiers), and many others. All these various names and identifiers that designate this compound are organized under the Synonyms section.

MeSH Entry Terms Medical Subject Heading (MeSH) names or identifiers matching this PubChem Compound record. The matching between the MeSH and compound records is performed by name matching (i.e., identical common names), as described in Kim et al., J. Cheminform., 2016, 8, 32. http://doi.org/10.1186/s13321-016-0142-6 Columns 76 alpha-ionone alpha-ionone, (+)-iosmer alpha-ionone, (E)-(+-)-isomer alpha-ionone, (E)-isomer

Depositor-Supplied Synonyms Chemical names provided by individual data contributors. Synonyms of Substances corresponding to a PubChem Compound record are combined. Some contributed names may be considered erroneous and filtered out. The link on each synonym shows which depositors provided that particular synonym for this structure. Columns true 75 ALPHA-IONONE 127-41-3 (E)-alpha-Ionone Iraldeine 4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one 3-Buten-2-one, 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-, (3E)- a-ionone alpha-Ionon (E)-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one Ionone, alpha- trans-alpha-Ionone alpha-(E)-ionone Irisone alpha-Ionone (natural) FEMA No. 2594 alpha-Cyclocitrylideneacetone Cyclocitrylideneacetone, alpha- (+-)-trans-alpha-Ionone (3E)-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one EINECS 204-841-6 EINECS 250-293-6 UNII-I9V075M61R 6901-97-9 DTXSID0035160 CHEBI:32319 3-Buten-2-one, 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-, (E)- I9V075M61R 4-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-3-buten-2-one EINECS 230-010-2 NSC 34560 (5E)-IONONE .alpha.-Cyclocitrylideneacetone AI3-16056 DTXCID8015160 HSDB 8268 .alpha.-Ionone (E)-(1)-4-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-3-buten-2-one NSC34560 MFCD00001565 31798-12-6 a-Ionone (>90%) beta-lonone (E)-4-(2,6,6-TRIMETHYL-2-CYCLOHEXEN-1-YL)-3-BUTEN-2-ONE beta-lonone (natural) alpha-Jonone alpha -ionone EINECS 232-396-8 EINECS 238-362-9 EINECS 250-812-6 IONONE, ALPHA alpha-Ionone, >=90% UNII-QP734LIN1K (+/-)-alpha-IONONE ALPHA-IONONE [FCC] QP734LIN1K (E)-.ALPHA.-IONONE alpha-Ionone (>90per cent) SCHEMBL112670 .ALPHA.-IONONE [MI] CHEMBL472877 .ALPHA.-IONONE [FHFI] alpha-Ionone, natural, >=86% alpha-Ionone, analytical standard (+/-)-.ALPHA.-IONONE (-)-4-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-3-buten-2-one Tox21_301173 alpha-Ionone, technical grade, 90% NSC-34560 STL570068 AKOS000120391 AKOS016843502 "4-(2,6,6-Trimethyl-cyclohex-2-e (+/-)-TRANS-.ALPHA.-IONONE DS-3418 alpha-Ionone, technical, >=90% (GC) NCGC00164008-01 NCGC00164008-02 NCGC00255071-01 CAS-127-41-3 CS-0149165 I0076 NS00012649 EN300-20383 A889200 W-108383 4-(2,6,6-Trimethyl-2-cyclohexenyl)-3-buten-2-one Q27114869 (e)-4-(2,6,6-trimethylcyclohex-2-enyl)but-3-en-2-one (3E)-4-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-3-buten-2-on 3-Buten-2-one, 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-, (E)-(.+/-.)-

Removed Synonyms Potentially erroneous chemical names and identifiers provided by PubChem Substance records for the same chemical structure that were removed by name/structure consistency filtering. true 75 IONONE |A-ionone Nat. Alpha Ionone Lonone (mixed isomers) BETA-IONONE alpha-Ionone Bri FCC AC1NQZHN alpha-ionone, (E)-isomer alpha-ionone, (+)-iosmer 4,7-Megastigmadien-9-one AC1Q1J9N FEMA No. 2595 UZFLPKAIBPNNCA-BQYQJAHWSA-N C13H20O alpha-ionone, (E)-(+-)-isomer <GREEK>A<P>-IONONE 25GM <GREEK>A<P>-IONONE 100GM C13-H20-O CID5282108 LS-2372 RTR-003944 alpha-Lonone, 92% - 100G 100g 2-(1,3-dithiolan-2-yl)-4-nitrophenol LS-84164 ST51038598 C12286 C011879 3-Buten-2-one,6,6-trimethyl-2-cyclohexen-1-yl)- 8013-90-9 3-Buten-2-one, 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)- I14-11279 I14-18012 Copaiba extract (resinoid) (South American spp. of Copaifera L.) (3E)-4-(2,6,6-trimethylcyclohex-2-enyl)but-3-en-2-one (S-(E))-4-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-3-buten-2-one 4-(2,6,6-trimethylcyclohex-2-ene-1-yl)-but-3-ene-2-one (?)-4-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-3-buten-2-one (E)-(+-)-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one [S-(E)]-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one 3-buten-2-ona, 4-(2,6,6-trimetil-2-ciclohexen-1-il)-, (3e)- 3-Buten-2-one, 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-, (-)- 14398-36-8 3-Buten-2-one, 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-, (S-(E))- 4 - (2,6,6 - trimethylcyclohex - 2 - ene - 1 - yl) - but - 3 - ene - 2 - one (+/-)-4-trans-(2,6,6-trimethyl-cyclohex-2-enyl)-but-3-en-2-one;(3E)-4-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-3-buten-2-one;(E)-alpha-Ionone;(E)-alpha-Ionone;(R,S)-3-(E)-Buten-2-one,4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-;4-(2,6,6-;4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-,(E)-3-Buten-2-one;4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one (alpha-ionone);(E)-4-(2,6,6-Trimethylcyclohex-2-en-1-yl)but-3-en-2-one 30685-95-1

Create Date Date when this compound record was created. For more information on various dates for PubChem records, visit the PubChem Record Dates help page. https://pubchem.ncbi.nlm.nih.gov/docs/record-dates true true 75 2005-03-26

Modify Date Date when this compound record was last modified. For more information on various dates for PubChem records, visit the PubChem Record Dates help page. https://pubchem.ncbi.nlm.nih.gov/docs/record-dates true true 75 2024-06-01

Chemical and Physical Properties Various chemical and physical properties that are experimentally determined for this compound. See also the Safety and Hazard Properties section (if available), which has additional properties pertinent to chemical safety and hazards.

Computed Properties Properties of this compound computed from its molecular formula and structure. Subsections 3 Property Name Property Value Reference Name Value Reference

Molecular Weight Molecular weight or molecular mass refers to the mass of a molecule. It is calculated as the sum of the mass of each constituent atom multiplied by the number of atoms of that element in the molecular formula. The molecular weight is also called the relative molar mass, because molecular weights are reported in daltons, which is defined relative to the mass of the isotope 12C (carbon 12). https://www.degruyter.com/document/doi/10.1515/pac-2017-1002/html?lang=en true 75 Computed by PubChem 2.2 (PubChem release 2021.10.14) 192.30 g/mol

XLogP3 XLogP3 is a predicted octanol-water partition coefficient, computed using the algorithm described in J. Chem. Inf. Model. 2007, 47, 6, 2140-2148. It is used as a measure of hydrophilicity or hydrophobicity of a molecule. https://pubmed.ncbi.nlm.nih.gov/17985865/ 75 XLogP3-AA Computed by XLogP3 3.0 (PubChem release 2021.10.14) 3

Hydrogen Bond Donor Count The number of hydrogen bond donors in this compound. 75 Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14) 0

Hydrogen Bond Acceptor Count The number of hydrogen bond acceptors in this compound. 75 Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14) 1

Rotatable Bond Count A rotatable bond is defined as any single-order non-ring bond, where atoms on either side of the bond are in turn bound to nonterminal heavy (i.e., non-hydrogen) atoms. That is, where rotation around the bond axis changes the overall shape of the molecule, and generates conformers which can be distinguished by standard fast spectroscopic methods. 75 Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14) 2

Exact Mass The exact mass of an isotopic species is obtained by summing the masses of the individual isotopes of the molecule. 75 Computed by PubChem 2.2 (PubChem release 2021.10.14) 192.151415257 g/mol

Monoisotopic Mass The monoisotopic mass is the sum of the masses of the atoms in a molecule using the unbound, ground-state, rest mass of the principal (most abundant) isotope for each element instead of the isotopic average mass. 75 Computed by PubChem 2.2 (PubChem release 2021.10.14) 192.151415257 g/mol

Topological Polar Surface Area The topological polar surface area (TPSA) is an estimate of the polar surface area (in Angstroms^2) of a molecule, computed as the surface sum over polar atoms in the molecule. The implementation follows the paper by Ertl et al. [J. Med. Chem. 2000, 43, 3714-3717]: only N and O are considered, 3D coordinates are not used, and there are various precomputed factors for different hybridizations, charges and participation in aromatic systems. https://pubmed.ncbi.nlm.nih.gov/11020286/ 75 Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14) 17.1 Ų

Heavy Atom Count The number of heavy atoms (i.e., non-hydrogen atoms) in this compound. 75 Computed by PubChem 14

Formal Charge Formal charge is the difference between the number of valence electrons of each atom and the number of electrons the atom is associated with. Formal charge assumes any shared electrons are equally shared between the two bonded atoms. 75 Computed by PubChem 0

Complexity The complexity rating of a compound is a rough estimate of how complicated a structure is, seen from both the point of view of the elements contained and the displayed structural features including symmetry. This complexity rating is computed using the Bertz/Hendrickson/Ihlenfeldt formula. https://pubchem.ncbi.nlm.nih.gov/docs/glossary#section=Complexity 75 Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14) 282

Isotope Atom Count Isotope atom count is the number of isotopes that are not most abundant for the corresponding chemical elements. Isotopes are variants of a chemical element which differ in neutron number. For example, among three isotopes of carbon (i.e., C-12, C-13, and C-14), the isotope atom count considers the C-13 and C-14 atoms, because C-12 is the most abundant isotope of carbon. 75 Computed by PubChem 0

Defined Atom Stereocenter Count An atom stereocenter, also known as a chiral center, is an atom that is attached to four different types of atoms (or groups of atoms) in the tetrahedral arrangement. It can have either (R)- or (S)- configurations. Some compounds, such as racemic mixtures, have an undefined atom stereocenter, whose (R/S)-configuration is not specifically defined. The "defined atom stereocenter count" is the number of atom stereocenters whose configurations are specifically defined. 75 Computed by PubChem 0

Undefined Atom Stereocenter Count The number of atom stereocenters whose configurations are not specifically defined. For the definition of atom stereocenters, see the "defined atom stereocenter count" above. 75 Computed by PubChem 1

Defined Bond Stereocenter Count A bond stereocenter is a non-rotatable bond around which two atoms can have different arrangement (as in cis- and trans-forms of butene around its double bond). Some compounds have an undefined bond stereocenter, whose stereochemistry is not specifically defined. The "defined bond stereocenter count" is the number of bond stereocenters whose configurations are specifically defined. 75 Computed by PubChem 1

Undefined Bond Stereocenter Count The number of bond stereocenters whose configurations are not specifically defined. For the definition of bond stereocenters, see the "defined bond stereocenter count" above. 75 Computed by PubChem 0

Covalently-Bonded Unit Count A covalently-bonded unit is a group of atoms connected by covalent bonds, ignoring other bond types (or a single atom without covalent bonds). The "covalently-bonded unit count" property is the number of such units in this compound compound. 75 Computed by PubChem 1

Compound Is Canonicalized Whether the compound has successfully passed PubChem's valence bond canonicalization procedure. Some large, complex, or highly symmetric structures may fail this process. 75 Computed by PubChem (release 2021.10.14) Yes

Experimental Properties Various experimentally determined properties for this compound. See also the Safety and Hazard Properties section (if available), which has additional properties pertinent to chemical safety and hazards.

Physical Description The appearance or features of this compound, including color, odor, state, taste and more in general. 13 Liquid; Dry Powder, Liquid 35 colourless to pale-yellow liquid with a warm, woody, violet-floral odour

Color/Form Color is the aspect of any object that may be described in terms of hue, lightness, and saturation. https://www.britannica.com/science/color 26 PEER REVIEWED O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 940 Colorless to slightly yellow liquid

Odor The property of certain chemicals, in very small concentrations, to stimulate chemical sense receptors that sample the air or water. https://www.britannica.com/science/odor 26 PEER REVIEWED Sell CS; Terpenoids. Kirk-Othmer Encyclopedia of Chemical Technology. (1999-2015). New York, NY: John Wiley & Sons. Online Posting Date: Sep 15, 2006. It has a warm, woody, floral odor with balsamic and sweet tones and is strongly reminiscent of violet flowers. 26 PEER REVIEWED O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 940 Sweet-floral odor, reminiscent of violets

Taste The sensation of flavor perceived in the mouth and throat on contact with a substance. https://www.britannica.com/science/taste-sense 26 PEER REVIEWED Burdock, G.A. (ed.). Fenaroli's Handbook of Flavor Ingredients. 6th ed.Boca Raton, FL 2010, p. 955 Woody, floral, berry, fruity with powdery nuances

Boiling Point The temperature at which this compound changes state from liquid to gas at a given atmospheric pressure. https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Chemistry_Lab_Techniques_(Nichols)/06%3A_Miscellaneous_Techniques/6.02%3A_Boiling_Point 26 PEER REVIEWED Sell CS; Terpenoids. Kirk-Othmer Encyclopedia of Chemical Technology. (1999-2015). New York, NY: John Wiley & Sons. Online Posting Date: Sep 15, 2006. 258 °C at 760 mm Hg 26 PEER REVIEWED O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 940 Pale yellow to yellow liquid; Specific gravity: 0.933-0.937 25/25 °C; Boiling point: 126-128 °C at 12 mm Hg /mixed ionone isomers/

Flash Point The lowest temperature at which a liquid can gives off vapor to form an ignitable mixture in air near the surface of the liquid. https://www.britannica.com/science/flash-point 26 PEER REVIEWED Sigma-Aldrich; Safety Data Sheet for alpha-Ionone. Product Number: I12409, Version 4.6 (Revision Date 07/09/2014). Available from, as of July 10, 2015: https://www.sigmaaldrich.com/safety-center.html 118 °C (244 °F) - closed cup

Solubility The solubility of a substance is the amount of that substance that will dissolve in a given amount of solvent. The default solvent is water, if not indicated. https://chem.libretexts.org/Courses/Purdue/Purdue%3A_Chem_26505%3A_Organic_Chemistry_I_(Lipton)/Chapter_4._Intermolecular_Forces_and_Physical_Properties/4.4_Solubility 26 PEER REVIEWED Etzweiler F et al; Anal Chem 67: 655-58 (1995) In water, 106 mg/L at 25 °C 3 5 https://pubchem.ncbi.nlm.nih.gov/compound/water PubChem Internal Link CID-962 26 PEER REVIEWED O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 940 Soluble in alcohol, most fixed oils, propylene glycol; insoluble in glycerin 37 16 https://pubchem.ncbi.nlm.nih.gov/compound/propylene%20glycol PubChem Internal Link CID-1030 68 8 https://pubchem.ncbi.nlm.nih.gov/compound/glycerin PubChem Internal Link CID-753 26 PEER REVIEWED O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 940 Miscible with absolute alcohol. Soluble in 2 to 3 parts of 70% alcohol, ether, chloroform, benzene. Very slightly soluble in water. /mixed ionone isomers/ 79 10 https://pubchem.ncbi.nlm.nih.gov/compound/chloroform PubChem Internal Link CID-6212 91 7 https://pubchem.ncbi.nlm.nih.gov/compound/benzene PubChem Internal Link CID-241 125 5 https://pubchem.ncbi.nlm.nih.gov/compound/water PubChem Internal Link CID-962 35 soluble in alcohol, propylene glycol, most fixed oils; insoluble in glycerol and water 20 16 https://pubchem.ncbi.nlm.nih.gov/compound/propylene%20glycol PubChem Internal Link CID-1030 68 8 https://pubchem.ncbi.nlm.nih.gov/compound/glycerol PubChem Internal Link CID-753 81 5 https://pubchem.ncbi.nlm.nih.gov/compound/water PubChem Internal Link CID-962 35 1 ml in 3 ml 70% alcohol; 1 ml in 10 ml 60% alcohol (in ethanol) 56 7 https://pubchem.ncbi.nlm.nih.gov/compound/ethanol PubChem Internal Link CID-702

Density This section provides information on the density (with unit) and specific gravity (without unit) of a compound. Density is mass of a unit volume of a compound and commonly expressed in units of kg/m3 or g/cm3. Specific gravity, also known as relative density, is a unit-less quantity, defined as the ratio of the density of a compound to that of a standard reference material (typically, water at 4 °C for liquids and air at room temperature [20 °C or 68 °F] for gases). https://chem.libretexts.org/Bookshelves/Introductory_Chemistry/Map%3A_Fundamentals_of_General_Organic_and_Biological_Chemistry_(McMurry_et_al.)/01%3A_Matter_and_Measurements/1.12%3A_Density_and_Specific_Gravity 26 PEER REVIEWED O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 940 0.9319 at 20/4 °C 35 0.927-0.933

Vapor Pressure Vapor pressure (or equilibrium vapor pressure) is the pressure of a vapor in thermodynamic equilibrium with its condensed phases in a closed system. https://chem.libretexts.org/Bookshelves/General_Chemistry/Map%3A_Chemistry_-_The_Central_Science_(Brown_et_al.)/11%3A_Liquids_and_Intermolecular_Forces/11.05%3A_Vapor_Pressure 26 PEER REVIEWED Ohe S; Computer Aided Data Book of Vapor Pressure. Data Book Publ. Co., Tokyo, Japan, p. 1671 (1976) 0.019 mm Hg at 25 C (extrapolated from higher temperatures)

LogP Log P is the partition coefficient expressed in logarithmic form. The partition coefficient is the ratio of concentrations of a compound in a mixture of two immiscible solvents at equilibrium. This ratio is therefore used to compare the solubilities of the solute in these two solvents. Because octanol and water are the most commonly used pair of solvents for measuring partition coefficients, the Log P values listed in this section refer to octanol/water partition coefficients, unless indicated otherwise. 26 PEER REVIEWED Griffin S et al; J Chromat A: 864: 221-228 (1999) log Kow = 3.85

Stability/Shelf Life Tendency of a material to resist change or decomposition due to internal reaction, or due to the action of air, heat, light, pressure, etc. See also the Stability and Reactivity subsection under the Safety and Hazards section on this page (when available). 26 PEER REVIEWED Sigma-Aldrich; Safety Data Sheet for alpha-Ionone. Product Number: I12409, Version 4.6 (Revision Date 07/09/2014). Available from, as of July 10, 2015: https://www.sigmaaldrich.com/safety-center.html Stable under recommended storage conditions.

Refractive Index The refractive index (also called index of refraction) of an optical medium is a dimensionless number that quantifies the light-bending ability of that medium. https://www.britannica.com/science/refractive-index 26 PEER REVIEWED Lide, D.R., G.W.A. Milne (eds.). Handbook of Data on Organic Compounds. Volume I. 3rd ed. CRC Press, Inc. Boca Raton ,FL. 1994., p. V2: 2006 Index of refraction: 1.4982 at 20 °C 35 1.497-1.502

Kovats Retention Index The Kovats retention index is a dimensionless quantity that characterizes the rate at which a compound is processed through a gas chromatography column. https://goldbook.iupac.org/terms/view/R05360 ThisSection 2 Name Value CommaSeparated 53 Standard non-polar 1413 1417 1410 1405 1401 1401 1428 1434 1416 1408 1413 1418 1420 1414.9 1416 1416 1410 1412 1419 1408 1445 1405 1402 1413 1416 1416 1407 1408 1399 1417 1400 1404 1404 1407 1407 1411 1414 1407 1407 1416 1403 1423.6 1423.6 1424 1424.3 53 Semi-standard non-polar 1427 1456 1426 1426 1433 1421 1430 1437 1426 1426 1437 1427 1426 1426 1429 1404 1419 1432 1421 1429 1426 1439 1429 1430 1433 1438 1391 1426 1426 1422 1422 1430 1420 1421 1426 1426 1433 1420 1424 1432 1381 1428 1422 1422 1422 1424 1430 1424 1430 1412 1426 1430 1422 1399 1430 1430 1434 1432.8 1432 1426 1430 1401 1418 1418 1426 1426 1427 1434 1422 1422 1426 1433 53 Standard polar 1863 1889 1839 1857 1805 1811 1809 1819 1854 1829 1849 1840 1829 1805 1860 1844 1858.3 1866 1888 1879 1879 1879 1831 1851 1853 1863 1818 1798 1801 1854.5 1818 1825 1833 1825 1833 1833 1842.3 1846.2

Other Experimental Properties Other experimental properties of this chemical. 26 PEER REVIEWED Fahlbusch KG et al; Flavors and Fragrances. Ullmann's Encyclopedia of Industrial Chemistry. 7th ed. (1999-2015). New York, NY: John Wiley & Sons. Online Posting Date: Jan 15, 2003. Both optical isomers of alpha-ionone are found in nature. Generally, ionones have a trans configuration. trans-alpha-Ionone can be converted into the cis-isomer by exposure to ultraviolet light. 24 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 105 18 https://pubchem.ncbi.nlm.nih.gov/compound/trans-alpha-Ionone PubChem Internal Link CID-5282108

Chemical Classes Chemical classes are groupings that relate chemicals by similar features. Chemicals can be classified by their structure (e.g., hydrocarbons), uses (e.g., pesticides), physical properties, radiological properties, or other factors.

Food Additives Chemicals are used as food additives. 21 Food addtives -> FDA Substances Added to Food (formerly EAFUS)

Fragrances Chemical substances are used fragrance products. 30 Fragrance Ingredient (alpha-Ionone) -> IFRA transparency List 22 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-Ionone PubChem Internal Link CID-5282108

Spectral Information Spectral data for this compound, including 1-D and 2-D nuclear magnetic resonance (NMR), Infrared (IR), Raman, and Ultraviolet (UV) spectroscopy, mass spectrometry (MS), and chromatography.

1D NMR Spectra One-dimensional (1D) nuclear magnetic resonance (NMR) spectra. ThisSection 2 Name Value 2 26 PEER REVIEWED Lide, D.R., G.W.A. Milne (eds.). Handbook of Data on Organic Compounds. Volume I. 3rd ed. CRC Press, Inc. Boca Raton ,FL. 1994., p. V2: 2006 1H-NMR: 616 (Varian Associates NMR spectra collection)

1H NMR Spectra Hydrogen-1 nuclear magnetic resonance (NMR) spectroscopy (also known as H1 NMR or proton NMR) is a version of NMR spectroscopy used to elucidate the structure of hydrogen-containing compounds. ThisSection 2 Name Value 2 28 Spectra ID https://hmdb.ca/spectra/nmr_one_d/3500 3500 28 Instrument Type JEOL 28 Frequency 90 MHz 28 Solvent CDCl3 28 Shifts [ppm]:Intensity 1.27:38.00, 6.77:51.00, 2.34:33.00, 2.00:40.00, 5.50:37.00, 1.28:40.00, 1.32:32.00, 1.41:35.00, 2.25:1000.00, 1.58:211.00, 1.56:177.00, 1.54:95.00, 1.49:37.00, 1.56:227.00, 2.11:37.00, 6.59:91.00, 6.13:118.00, 6.67:51.00, 2.06:42.00, 6.49:98.00, 1.98:36.00, 2.02:45.00, 5.95:64.00, 2.08:38.00, 1.53:80.00, 0.86:459.00, 5.95:62.00, 0.93:441.00, 2.22:53.00, 2.04:44.00, 2.07:30.00, 1.57:175.00, 2.09:33.00, 1.07:34.00, 5.49:31.00, 1.40:37.00, 1.60:82.00, 1.60:74.00 28 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/nmr.cgi?peaks=1.27:38.00,6.77:51.00,2.34:33.00,2.00:40.00,5.50:37.00,1.28:40.00,1.32:32.00,1.41:35.00,2.25:1000.00,1.58:211.00,1.56:177.00,1.54:95.00,1.49:37.00,1.56:227.00,2.11:37.00,6.59:91.00,6.13:118.00,6.67:51.00,2.06:42.00,6.49:98.00,1.98:36.00,2.02:45.00,5.95:64.00,2.08:38.00,1.53:80.00,0.86:459.00,5.95:62.00,0.93:441.00,2.22:53.00,2.04:44.00,2.07:30.00,1.57:175.00,2.09:33.00,1.07:34.00,5.49:31.00,1.40:37.00,1.60:82.00,1.60:74.00 https://pubchem.ncbi.nlm.nih.gov/image/nmr.cgi?peaks=1.27:38.00,6.77:51.00,2.34:33.00,2.00:40.00,5.50:37.00,1.28:40.00,1.32:32.00,1.41:35.00,2.25:1000.00,1.58:211.00,1.56:177.00,1.54:95.00,1.49:37.00,1.56:227.00,2.11:37.00,6.59:91.00,6.13:118.00,6.67:51.00,2.06:42.00,6.49:98.00,1.98:36.00,2.02:45.00,5.95:64.00,2.08:38.00,1.53:80.00,0.86:459.00,5.95:62.00,0.93:441.00,2.22:53.00,2.04:44.00,2.07:30.00,1.57:175.00,2.09:33.00,1.07:34.00,5.49:31.00,1.40:37.00,1.60:82.00,1.60:74.00 image/svg 68 Source of Spectrum Sigma-Aldrich Co. LLC. 68 Source of Sample Sigma-Aldrich Co. LLC. 68 Catalog Number I12409 68 Copyright Copyright © 2021-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2021 John Wiley & Sons, Inc. All Rights Reserved. 68 Thumbnail https://spectrabase.com/spectrum/7zHL5kFbzPw https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/13586321_1 image/png

13C NMR Spectra Carbon-13 nuclear magnetic resonance (NMR) spectroscopy (also known as 13C NMR) is a version of NMR spectroscopy used to elucidate the structure of carbon-containing compounds. ThisSection 2 Name Value 2 29 Spectra ID https://hmdb.ca/spectra/nmr_one_d/3642 3642 29 Instrument Type Varian 29 Frequency 25.16 MHz 29 Solvent CDCl3 29 Shifts [ppm]:Intensity 132.38:1000.00, 198.26:604.00, 31.27:847.00, 26.83:698.00, 27.80:688.00, 23.04:807.00, 54.34:931.00, 131.95:995.00, 22.77:649.00, 148.93:960.00, 32.53:787.00, 26.94:554.00, 122.68:871.00 29 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/nmr.cgi?peaks=132.38:1000.00,198.26:604.00,31.27:847.00,26.83:698.00,27.80:688.00,23.04:807.00,54.34:931.00,131.95:995.00,22.77:649.00,148.93:960.00,32.53:787.00,26.94:554.00,122.68:871.00 https://pubchem.ncbi.nlm.nih.gov/image/nmr.cgi?peaks=132.38:1000.00,198.26:604.00,31.27:847.00,26.83:698.00,27.80:688.00,23.04:807.00,54.34:931.00,131.95:995.00,22.77:649.00,148.93:960.00,32.53:787.00,26.94:554.00,122.68:871.00 image/svg 56 Source of Sample Tokyo Kasei Kogyo Company, Ltd., Tokyo, Japan 56 Copyright Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved. 56 Thumbnail https://spectrabase.com/spectrum/GKmjGMuUUZs https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/4621470_1 image/png 62 Instrument Name BRUKER AM-360 62 Copyright Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved. 62 Thumbnail https://spectrabase.com/spectrum/7iFEQnZ32rh https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/9781500_1 image/png

Mass Spectrometry Mass spectrometry (MS or mass spec) is a technique to determine molecular structure through ionization and fragmentation of the parent compound into smaller components. https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modules_(Organic_Chemistry)/Spectroscopy/Mass_Spectrometry ThisSection 2 Name Value 2

GC-MS Data from gas chromatography-mass spectrometry (GC-MS) experiments. https://chem.libretexts.org/Bookshelves/General_Chemistry/Book%3A_Structure_and_Reactivity_in_Organic_Biological_and_Inorganic_Chemistry_(Schaller)/II%3A_Practical_Aspects_of_Structure_-_Purification_and_Spectroscopy/06%3A_Introductory_Mass_Spectrometry/6.03%3A_GC-MS_and_LC-MS ThisSection 2 Name Value 2 39 MoNA ID https://mona.fiehnlab.ucdavis.edu/spectra/display/JP002591 JP002591 39 MS Category Experimental 39 MS Type GC-MS 39 MS Level MS1 39 Instrument HITACHI RMU-6M 39 Instrument Type EI-B 39 Ionization Mode positive 39 Top 5 Peaks 121 99.99 93 86.80 136 74.47 43 71.48 41 27.15 39 SPLASH https://mona.fiehnlab.ucdavis.edu/spectra/browse?query=exists(splash.splash:%27splash10-0006-9600000000-f52514927b7c7e5bd79a%27) splash10-0006-9600000000-f52514927b7c7e5bd79a 39 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=121:99.99,93:86.80,136:74.47,43:71.48,41:27.15 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=121:99.99,93:86.80,136:74.47,43:71.48,41:27.15 image/svg 39 License CC BY-NC-SA 40 MoNA ID https://mona.fiehnlab.ucdavis.edu/spectra/display/JP006612 JP006612 40 MS Category Experimental 40 MS Type GC-MS 40 MS Level MS1 40 Instrument HITACHI M-80B 40 Instrument Type EI-B 40 Ionization Mode positive 40 Top 5 Peaks 121 99.99 93 79.04 43 73.91 136 53.76 91 29.66 40 SPLASH https://mona.fiehnlab.ucdavis.edu/spectra/browse?query=exists(splash.splash:%27splash10-0006-9600000000-93c21f85616fb52a6763%27) splash10-0006-9600000000-93c21f85616fb52a6763 40 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=121:99.99,93:79.04,43:73.91,136:53.76,91:29.66 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=121:99.99,93:79.04,43:73.91,136:53.76,91:29.66 image/svg 40 License CC BY-NC-SA 41 MoNA ID https://mona.fiehnlab.ucdavis.edu/spectra/display/JP007557 JP007557 41 MS Category Experimental 41 MS Type GC-MS 41 MS Level MS1 41 Instrument HITACHI M-80 41 Instrument Type EI-B 41 Ionization Mode positive 41 Top 5 Peaks 121 99.99 93 93.05 136 88.07 43 42.18 109 26.01 41 SPLASH https://mona.fiehnlab.ucdavis.edu/spectra/browse?query=exists(splash.splash:%27splash10-0076-6900000000-0d604eb8b56437636516%27) splash10-0076-6900000000-0d604eb8b56437636516 41 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=121:99.99,93:93.05,136:88.07,43:42.18,109:26.01 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=121:99.99,93:93.05,136:88.07,43:42.18,109:26.01 image/svg 41 License CC BY-NC-SA 45 NIST Number 232725 45 Library Main library 45 Total Peaks 154 45 m/z Top Peak 121 45 m/z 2nd Highest 43 45 m/z 3rd Highest 93 45 Thumbnail https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/107877_1 image/png 46 NIST Number 233311 46 Library Main library 46 Total Peaks 136 46 m/z Top Peak 121 46 m/z 2nd Highest 93 46 m/z 3rd Highest 136 46 Thumbnail https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/108432_1 image/png 47 NIST Number 65173 47 Library Main library 47 Total Peaks 71 47 m/z Top Peak 121 47 m/z 2nd Highest 93 47 m/z 3rd Highest 136 47 Thumbnail https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/108433_1 image/png 48 NIST Number 8317 48 Library Replicate library 48 Total Peaks 162 48 m/z Top Peak 121 48 m/z 2nd Highest 93 48 m/z 3rd Highest 43 48 Thumbnail https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/266819_1 image/png 49 NIST Number 22354 49 Library Replicate library 49 Total Peaks 56 49 m/z Top Peak 121 49 m/z 2nd Highest 93 49 m/z 3rd Highest 43 49 Thumbnail https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/266820_1 image/png 50 NIST Number 53387 50 Library Replicate library 50 Total Peaks 108 50 m/z Top Peak 121 50 m/z 2nd Highest 93 50 m/z 3rd Highest 136 50 Thumbnail https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/266847_1 image/png 51 NIST Number 285350 51 Library Replicate library 51 Total Peaks 61 51 m/z Top Peak 121 51 m/z 2nd Highest 93 51 m/z 3rd Highest 136 51 Thumbnail https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/266848_1 image/png 52 NIST Number 194313 52 Library Replicate library 52 Total Peaks 160 52 m/z Top Peak 121 52 m/z 2nd Highest 93 52 m/z 3rd Highest 136 52 Thumbnail https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/266850_1 image/png 60 Source of Spectrum Chemical Concepts, A Wiley Division, Weinheim, Germany 60 Copyright Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved. 60 Thumbnail https://spectrabase.com/spectrum/KnudVAfFKn8 https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/9781497_1 image/png 61 Instrument Name 311A 61 Source of Spectrum Chemical Concepts, A Wiley Division, Weinheim, Germany 61 Copyright Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved. 61 Thumbnail https://spectrabase.com/spectrum/GJGB9xsccAG https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/9781498_1 image/png

Other MS This section provides this compound's mass spectrometry (MS) information that is not shown in other sections. ThisSection 2 Name Value 2 26 PEER REVIEWED Lide, D.R., G.W.A. Milne (eds.). Handbook of Data on Organic Compounds. Volume I. 3rd ed. CRC Press, Inc. Boca Raton ,FL. 1994., p. V2: 2006 MASS: 1340 (Atlas of Spectral Data, John Wiley & Sons, New York)

UV Spectra Ultraviolet (UV) spectroscopy (or Spectrophotometry) is an analytical technique used to measure how much a molecule absorbs light in the ultraviolet spectral region. This technique is particularly useful to study aromatic, conjugated, and other substances containing a pi bond. Modern ultraviolet spectrophotometers also cover the visible light range, in which case the technique is called ultraviolet-visible (UV-Vis) spectroscopy. https://chem.libretexts.org/Courses/Brevard_College/CHE_202%3A_Organic_Chemistry_II/05%3A_Structural__Determination_I/5.05%3A_Ultraviolet_and_visible_spectroscopy 26 PEER REVIEWED Lide, D.R., G.W.A. Milne (eds.). Handbook of Data on Organic Compounds. Volume I. 3rd ed. CRC Press, Inc. Boca Raton ,FL. 1994., p. V2: 2006 UV: 5-386 (Phillip et al; Organic Electronic Spectral Data, John Wiley & Sons, New York)

IR Spectra Infrared spectroscopy (IR spectroscopy) is the spectroscopy that deals with the infrared region of the electromagnetic spectrum extending from 780 nm to about 20000 nm. The IR spectra tells you what types of vibrational mode (motion) responses occur in a molecule interacting with infrared light. It is used to help determine the functional groups in a molecule. https://chem.libretexts.org/Bookshelves/Physical_and_Theoretical_Chemistry_Textbook_Maps/Supplemental_Modules_(Physical_and_Theoretical_Chemistry)/Spectroscopy/Vibrational_Spectroscopy/Infrared_Spectroscopy ThisSection 2 Name Value 2 26 PEER REVIEWED Lide, D.R., G.W.A. Milne (eds.). Handbook of Data on Organic Compounds. Volume I. 3rd ed. CRC Press, Inc. Boca Raton ,FL. 1994., p. V2: 206 IR: 5906 (Sadtler Research Laboratories IR prism collection)

FTIR Spectra Fourier transform infrared spectroscopy (FTIR) results for this chemical. https://chem.libretexts.org/Courses/Howard_University/Howard%3A_Physical_Chemistry_Laboratory/14._Fourier_Transform_Infrared_Spectroscopy_(FTIR) ThisSection 2 Name Value 2 55 Technique CAPILLARY CELL: NEAT 55 Source of Sample Magnus, Mabee & Reynard, Inc., New York, New York 55 Copyright Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved. 55 Thumbnail https://spectrabase.com/spectrum/6eaTprYXZjt https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/4621469_1 image/png 57 Instrument Name Bruker IFS 85 57 Technique Film 57 Copyright Copyright © 1989, 1990-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved. 57 Thumbnail https://spectrabase.com/spectrum/2LHqg51Vkrl https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/9781494_1 image/png

ATR-IR Spectra Attenuated total reflection infrared (ATR-IR) spectral data. ATR is a sampling technique that enables samples to be examined directly in the solid or liquid state without further preparation. ATR-IR can be applied to the same chemical or biological systems as the transmission IR. An advantage of ATR-IR over the transmission IR is the limited path length into the sample, because ATR-IR avoids the problem of strong attenuation of the IR signal in highly absorbing media such as aqueous solutions. https://chem.libretexts.org/Bookshelves/Analytical_Chemistry/Supplemental_Modules_(Analytical_Chemistry)/Instrumental_Analysis/Spectrometer/ATR-FTIR ThisSection 2 Name Value 2 64 Instrument Name Bruker Tensor 27 FT-IR 64 Technique ATR-Neat (DuraSamplIR II) 64 Source of Spectrum Bio-Rad Laboratories, Inc. 64 Source of Sample Sigma-Aldrich Company Llc. 64 Catalog Number W259403 64 Lot Number MKBJ4923V 64 Copyright Copyright © 2014-2024 John Wiley & Sons, Inc. All Rights Reserved. 64 Thumbnail https://spectrabase.com/spectrum/LL3ynnehcLF https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/9781527_1 image/png 65 Source of Sample Aldrich 65 Catalog Number I12409 65 Copyright Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved. 65 Thumbnail https://spectrabase.com/spectrum/GvqjEAdBObj https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/9781556_1 image/png

Near IR Spectra Near infrared (NIR) spectroscopy is a spectroscopic method that uses the near-infrared region of the electromagnetic spectrum (from 780 nm to 2500 nm). https://chem.libretexts.org/Bookshelves/Physical_and_Theoretical_Chemistry_Textbook_Maps/Supplemental_Modules_(Physical_and_Theoretical_Chemistry)/Spectroscopy/Vibrational_Spectroscopy/Infrared_Spectroscopy/Infrared_Spectroscopy ThisSection 2 Name Value 2 58 Instrument Name BRUKER IFS 88 58 Technique NIR Spectrometer= INSTRUMENT PARAMETERS=INST=BRUKER,RSN=3629,REO=2,CNM=HEI,ZFF=2 58 Source of Spectrum Prof. Buback, University of Goettingen, Germany 58 Copyright Copyright © 1989, 1990-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved. 58 Thumbnail https://spectrabase.com/spectrum/emWYHfM2JY https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/9781495_1 image/png 59 Instrument Name BRUKER IFS 88 59 Technique NIR Spectrometer= INSTRUMENT PARAMETERS=INST=BRUKER,RSN=3629,REO=2,CNM=HEI,ZFF=2 59 Source of Spectrum Prof. Buback, University of Goettingen, Germany 59 Copyright Copyright © 1989, 1990-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved. 59 Thumbnail https://spectrabase.com/spectrum/LYp6qOV659t https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/9781496_1 image/png

Vapor Phase IR Spectra Infrared (IR) spectral data recorded in the vapor phase (gas) of this chemical. https://chem.libretexts.org/Bookshelves/Physical_and_Theoretical_Chemistry_Textbook_Maps/Supplemental_Modules_(Physical_and_Theoretical_Chemistry)/Spectroscopy/Vibrational_Spectroscopy/Infrared_Spectroscopy ThisSection 2 Name Value 2 66 Technique Vapor Phase 66 Source of Spectrum Sigma-Aldrich Co. LLC. 66 Source of Sample Aldrich 66 Catalog Number I12409 66 Copyright Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved. 66 Thumbnail https://spectrabase.com/spectrum/hpSRzykhzR https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/9781559_1 image/png 69 Source of Spectrum Sigma-Aldrich Co. LLC. 69 Source of Sample Sigma-Aldrich Co. LLC. 69 Catalog Number I12409 69 Copyright Copyright © 2021-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2021 John Wiley & Sons, Inc. All Rights Reserved. 69 Thumbnail https://spectrabase.com/spectrum/CaP6WsJy2Nq https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/13586322_1 image/png

Raman Spectra Raman spectroscopy is a spectroscopic technique typically used to study vibrational modes of a molecular system, although it can also be used to observe rotational and other low-frequency modes of the system. Raman spectroscopy is based on inelastic scattering of photons, known as Raman scattering. https://chem.libretexts.org/Bookshelves/Analytical_Chemistry/Map%3A_Principles_of_Instrumental_Analysis_(Skoog_et_al.)/18%3A_Raman_Spectroscopy ThisSection 2 Name Value 2 63 Instrument Name Bruker MultiRAM Stand Alone FT-Raman Spectrometer 63 Technique FT-Raman 63 Source of Spectrum Bio-Rad Laboratories 63 Source of Sample Sigma-Aldrich Company Llc. 63 Catalog Number W259403 63 Lot Number MKBJ4923V 63 Copyright Copyright © 2014-2024 John Wiley & Sons, Inc. All Rights Reserved. 63 Thumbnail https://spectrabase.com/spectrum/3NYFpDjUb38 https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/9781526_1 image/png 67 Catalog Number I12409 67 Copyright Copyright © 2017-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2017-2024 John Wiley & Sons, Inc. All Rights Reserved. 67 Thumbnail https://spectrabase.com/spectrum/5skKlG6C3jA https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/9781560_1 image/png

Related Records Records related to this compound. This includes PubChem compound and substance records, as well as records in NCBI resources (e.g., PubMed, Gene, Protein Structure, and Taxonomy) and other databases external to NCBI.

Related Compounds with Annotation Compound records that are closely related to this record AND that have biomedical annotations. In essence, they are a subset of the compounds included in the "Related Compounds" section below this section. The "Related Compounds" include the parent, components, mixtures, and salt forms of this compound record as well as the "similar compounds" and "similar conformers", which are structurally similar to this record in terms of 2-D and 3-D chemical structure similarity measures, respectively, as explained in Kim et al., J. Cheminform. 2016, 8, 62. https://doi.org/10.1186/s13321-016-0163-1 75 true

Related Compounds Compound records closely related to this record. It includes compounds which are the parent, components, mixtures, and salt forms of this compound record. It also includes the "similar compounds" and "similar conformers", which are structurally similar to this record in terms of 2-D and 3-D chemical structure similarity measures, respectively, as explained in Kim et al., J. Cheminform. 2016, 8, 62. https://doi.org/10.1186/s13321-016-0163-1 ThisSection 2 Name Value 1 75 Same Connectivity Count https://pubchem.ncbi.nlm.nih.gov/rest/pug/compound/cid/5282108/cids/JSON?cids_type=same_connectivity&list_return=redirect 9 75 Same Parent, Connectivity Count https://pubchem.ncbi.nlm.nih.gov/rest/pug/compound/cid/5282108/cids/JSON?cids_type=same_parent_connectivity&list_return=redirect 11 75 Same Parent, Exact Count https://pubchem.ncbi.nlm.nih.gov/rest/pug/compound/cid/5282108/cids/JSON?cids_type=same_parent&list_return=redirect 3 75 Mixtures, Components, and Neutralized Forms Count https://pubchem.ncbi.nlm.nih.gov/rest/pug/compound/cid/5282108/cids/JSON?cids_type=component&list_return=redirect 34 75 Similar Compounds Count https://pubchem.ncbi.nlm.nih.gov/rest/pug/compound/cid/5282108/cids/JSON?cids_type=similar_2d&list_return=redirect 411 75 Similar Conformers Count https://pubchem.ncbi.nlm.nih.gov/rest/pug/compound/cid/5282108/cids/JSON?cids_type=similar_3d&list_return=redirect 1512

Substances Substance records associated with this compound. In PubChem, the term "substance" refers to depositor-provided data for a chemical.. https://pubchem.ncbi.nlm.nih.gov/docs/substances

PubChem Reference Collection SID Substances from the special PubChem Reference Collection associated with this compound. true 75 https://pubchem.ncbi.nlm.nih.gov/substance/482043033 482043033

Related Substances Substance records related to this compound (e.g., the standardized chemical structures of these substances are the same as this compound or correspond to a mixture containing this compound as a component). ThisSection 2 Name Value 1 75 All Count https://pubchem.ncbi.nlm.nih.gov/rest/pug/compound/cid/5282108/sids/JSON?sids_type=all&list_return=redirect 199 75 Same Count https://pubchem.ncbi.nlm.nih.gov/rest/pug/compound/cid/5282108/sids/JSON?sids_type=standardized&list_return=redirect 145 75 Mixture Count https://pubchem.ncbi.nlm.nih.gov/rest/pug/compound/cid/5282108/sids/JSON?sids_type=component&list_return=redirect 54

Substances by Category Substances associated with this compound, grouped by the category of the data sources who submitted the substances to PubChem (e.g., government organizations, chemical vendors, research and development, curation efforts, NIH initiatives, etc.). 75 Chemical Vendors Curation Efforts Governmental Organizations Journal Publishers Legacy Depositors NIH Initiatives Research and Development Subscription Services

Other Relationships Other types of related records, such as alternative forms, monomers or polymers, components of important mixtures, etc. In this table, the relationship is in parentheses, and the implied grammar is "the compound summarized on this page ... has this relationship to ... this item in the table." Columns 75 Calendula Officinalis Flower (part of) 0 28 https://pubchem.ncbi.nlm.nih.gov/compound/Calendula%20Officinalis%20Flower

Entrez Crosslinks Cross-references to associated records in other Entrez databases such as PubMed, Gene, Protein, etc. ThisSection 2 Name Value 1 75 PubMed Count https://www.ncbi.nlm.nih.gov/sites/entrez?LinkName=pccompound_pubmed&db=pccompound&cmd=Link&from_uid=5282108 2 75 Taxonomy Count https://www.ncbi.nlm.nih.gov/sites/entrez?LinkName=pccompound_taxonomy&db=pccompound&cmd=Link&from_uid=5282108 1 75 Gene Count https://www.ncbi.nlm.nih.gov/sites/entrez?LinkName=pccompound_gene&db=pccompound&cmd=Link&from_uid=5282108 2

Chemical Vendors A list of chemical vendors that sell this compound. Note that the order of chemical vendors on the list is randomized, and that PubChem do not endorse any of the vendors. Each vendor may have multiple products containing the same chemical, but different in various aspects, such as amount and purity. For each product, the external identifier used to locate the product on the vendor's website is provided under the Purchasable Chemical column, and clicking this identifier directs you to the vendor's website. The information on the product provided by the vendor to PubChem can be accessed at the Summary page of the corresponding PubChem Substance ID (SID). 75 true

Food Additives and Ingredients This section provides information on chemicals found in food (e.g., food additives, flavoring and coloring agents).

Food Additive Classes Classification of this compound as a chemical found in food (e.g., food additive, food contaminant, or veterinary drug). The source of information in this section includes the EU Food improvement agents and Evaluations of the Joint FAO/WHO Expert Committee on Food Additives (JECFA). 16 Flavoring Agents 34 JECFA Functional Classes Flavouring Agent -> FLAVOURING_AGENT; 35 Flavoring Agents 36 JECFA Functional Classes Flavouring Agent -> FLAVOURING_AGENT;

FEMA Flavor Profile The Flavor Profile describes the general type of flavor that this chemical contributes. This profile is from the Flavor Ingredient Library of the Flavor and Extract Manufacturers Association (FEMA). https://www.femaflavor.org/flavor-library 23 FEMA Flavor Profile Violet, Wood

FDA Substances Added to Food The FDA Substance Added to Food inventory includes the ingredients regulated by the U.S. Food and Drug Administration (e.g., food additives, color additives, and flavoring substances). The Substances Added to Food inventory replaces what was previously known as Everything Added to Foods in the United States (EAFUS). https://www.fda.gov/food/food-additives-petitions/substances-added-food-formerly-eafus ThisSection 2 Name Value 21 Substance https://www.cfsanappsexternal.fda.gov/scripts/fdcc/index.cfm?set=FoodSubstances&id=IONONEalpha ALPHA-IONONE 21 Used for (Technical Effect) FLAVORING AGENT OR ADJUVANT 21 Document Number (21 CFR) 172.515 0 7 https://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfCFR/CFRSearch.cfm?fr=172.515

Associated Foods This section provides the related foods that contain the compound as an ingredient, flavor, or other aspects. Columns 24 collection=consolidatedcompoundtaxonomy&view=concise_cid_food&srccmpdkind='Food Compound'

Evaluations of the Joint FAO/WHO Expert Committee on Food Additives - JECFA Evaluations of the Joint FAO/WHO Expert Committee on Food Additives (JECFA) database contains the summaries of all the evaluations of flavors, food additives, contaminants, toxicants and veterinary drugs. Each summary contains basic chemical information, ADIs/TDIs (acceptable daily intake / tolerable daily intake), links to the most recent reports and monographs as well as to the specification database, and a history of JECFA evaluations. https://apps.who.int/food-additives-contaminants-jecfa-database/ ThisSection 2 Name Value 34 Chemical Name alpha-CYCLOCITRYLIDENEACETONE 0 29 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-CYCLOCITRYLIDENEACETONE PubChem Internal Link CID-5282108 34 Evaluation Year 1998 34 ADI 0-0.1 mg/kg bw (1984) 34 Comments No safety concern at current levels of intake when used as a flavouring agent. The 1984 group ADI of 0-0.1 mg/kg bw for alpha-ionone and beta-ionone, singly or in combination, was maintained at the fifty-first meeting (1998). 120 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 137 11 https://pubchem.ncbi.nlm.nih.gov/compound/beta-ionone PubChem Internal Link CID-638014 34 Report TRS 891-JECFA 51/96 0 19 http://apps.who.int/iris/bitstream/10665/42245/1/WHO_TRS_891.pdf 34 Tox Monograph FAS 42-JECFA 51/335 0 19 http://www.inchem.org/pages/jecfa.html 36 Chemical Name alpha-IONONE 36 Evaluation Year 1998 36 ADI 0-0.1 mg/kg bw (1984) 36 Comments No safety concern at current levels of intake when used as a flavouring agent. The 1984 group ADI of 0-0.1 mg/kg bw for alpha-ionone and beta-ionone, singly or in combination, was maintained at the fifty-first meeting (1998). 120 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 137 11 https://pubchem.ncbi.nlm.nih.gov/compound/beta-ionone PubChem Internal Link CID-638014 36 Report TRS 891-JECFA 51/96 0 19 http://apps.who.int/iris/bitstream/10665/42245/1/WHO_TRS_891.pdf 36 Tox Monograph FAS 42-JECFA 51/335 0 19 http://www.inchem.org/pages/jecfa.html

Pharmacology and Biochemistry Pharmacology and biochemistry information related to this compound, including the pharmacodynamics, pharmacokinetics, metabolism, mechanism of action, biological half-life, biochemical reactions, and many others.

Absorption, Distribution and Excretion 26 PEER REVIEWED WHO; WHO Food Additive Series 19. Ionone (1984). Available from as of July 15, 2015: https://www.inchem.org Following oral administration, alpha-ionone undergoes biochemical oxidation in the rabbit and is excreted in the urine, principally, as 5-oxo-cis-tetrahydro-ionone, indicating in vivo oxidation of carbon atom 5 in the ionone structure. 31 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 197 6 https://pubchem.ncbi.nlm.nih.gov/element/Carbon PubChem Internal Link Element-Carbon

Metabolism/Metabolites Metabolites are substances made or used when the body breaks down food, drugs or chemicals, or its own tissue (for example, fat or muscle tissue). This process is called metabolism and makes energy and the materials needed for growth, reproduction, and maintaining health. Metabolism also helps get rid of toxic substances. 26 PEER REVIEWED Lalko J et al; Food Chem Toxicol 45 Suppl 1: S235-40 (2007) Two rabbits were fed a single dose of 170 g of pure alpha-ionone. Urine was collected and ether soluble compounds were extracted. The major urinary metabolite was identified as 5-oxo-cis-tetrahydroionone. 52 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 187 16 https://pubchem.ncbi.nlm.nih.gov/compound/tetrahydroionone PubChem Internal Link CID-110787

Human Metabolite Information Information on metabolites generated from this compound in the human body. The data in this section is from the Human Metabolome Database. https://hmdb.ca/

Cellular Locations Cellular locations of this compound or its metabolites (e.g., cytoplasm, nucleus, lysosome, mitochondria, membrane, extracelluar). Columns 27 Cellular Locations Membrane

Use and Manufacturing This section provides information on the use and manufacturing information for this chemical, such as uses, consumption patterns, manufacturing methods, and U.S. imports/exports/production.

Uses Major uses of this chemical, including both consumer uses and industrial uses. 12 EPA CPDat Chemical and Product Categories The Chemical and Products Database, a resource for exposure-relevant data on chemicals in consumer products, Scientific Data, volume 5, Article number: 180125 (2018), DOI:10.1038/sdata.2018.125 cpdat 26 PEER REVIEWED National Pesticide Information Retrieval System's Database on alpha-Ionone (127-41-3). Available from, as of June 12, 2015: https://npirspublic.ceris.purdue.edu/ppis/ For alpha-ionone (USEPA/OPP Pesticide Code: 129030) ACTIVE products with label matches. /SRP: Registered for use in the USA but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./ 4 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 26 PEER REVIEWED Burdock, G.A. (ed.). Fenaroli's Handbook of Flavor Ingredients. 6th ed.Boca Raton, FL 2010, p. 955 Reported uses (ppm): Table: Reported uses (ppm): (Flavor and Extract Manufacturers' Association, 1994) [Table#8259] 82 12 Inline Table [Table#8259] 26 [Table#8259] IkZvb2QgQ2F0ZWdvcnkiLCJVc3VhbCIsIk1heC4iCiJBbGNvaG9saWMgYmV2ZXJhZ2VzIiwiMS4w MCIsIjMuMDAiCiJCYWtlZCBnb29kcyIsIjQuODIiLCI5LjQ1IgoiQ2hld2luZyBndW0iLCI1OC4x MSIsIjU4LjExIgoiRnJvemVuIGRhaXJ5IiwiMS42MiIsIjMuOTQiCiJHZWxhdGlucywgcHVkZGlu Z3MiLCIyLjk1IiwiOC4wOSIKIkhhcmQgY2FuZHkiLCI2LjIzIiwiNi4zNiIKIk5vbmFsY29ob2xp YyBiZXZlcmFnZXMiLCIxLjEwIiwiMi4zNiIKIlNvZnQgY2FuZHkiLCI1LjUwIiwiMTAuMTkiCg== text/csv 26 PEER REVIEWED O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 940 Fragrance ingredient in perfumery, in cosmetics and personal care products, in household cleaners and detergents. Flavoring agent in beverages, baked goods, and candies. 26 PEER REVIEWED USEPA/OPPTS; Floral Attractants, Repellents, and Insecticides Fact Sheet. 2004. Available from, as of Jul 14, 2015: https://www.epa.gov/opp00001/chem_search/reg_actions/registration/fs_G-105_25-Sep-00.pdf Used as an ingredient in dog/cat repellent; attracts adult rose chafers (a beetle).

Use Classification This section contains use classification/category information for this compound from various sources. 16 Food additives -> Flavoring Agents 30 Fragrance Ingredients 34 Flavouring Agent -> FLAVOURING_AGENT; -> JECFA Functional Classes 35 Flavoring Agents -> JECFA Flavorings Index 36 Flavouring Agent -> FLAVOURING_AGENT; -> JECFA Functional Classes

Industry Uses Categories of functional use of this chemical in industry. Columns 13 https://www.epa.gov/chemical-data-reporting Odor agents Fragrance

Consumer Uses Consumer uses of this chemical and products containing it (e.g., chemical-specific product categories). Columns 13 https://www.epa.gov/chemical-data-reporting Odor agents Fragrance

Household Products Household products containing this compound. This information is from several sources, including the Consumer Product Information Database (CPID). https://www.whatsinproducts.com/ 10 Household & Commercial/Institutional Products Information on 12 consumer products that contain Alpha-Ionone in the following categories is provided: 49 12 https://pubchem.ncbi.nlm.nih.gov/compound/Alpha-Ionone PubChem Internal Link CID-5282108 • Auto Products • Inside the Home

Methods of Manufacturing Methods of producing this compound in an industrial scale, provided by the Hazardous Substances Data Bank (HSDB). https://pubchem.ncbi.nlm.nih.gov/source/11933 26 PEER REVIEWED Burdock, G.A. (ed.). Fenaroli's Handbook of Flavor Ingredients. 6th ed.Boca Raton, FL 2010, p. 955 By condensing citral with acetone to form pseudoionone, which is then cyclized by acid-type reagents. 14 6 https://pubchem.ncbi.nlm.nih.gov/compound/citral PubChem Internal Link CID-638011 26 7 https://pubchem.ncbi.nlm.nih.gov/compound/acetone PubChem Internal Link CID-180 42 12 https://pubchem.ncbi.nlm.nih.gov/compound/pseudoionone PubChem Internal Link CID-1757003

Formulations/Preparations Information on Formulations/Preparations of this chemical, collected by the Hazardous Substances Data Bank (HSDB) from various sources. https://pubchem.ncbi.nlm.nih.gov/source/11933 26 PEER REVIEWED National Pesticide Information Retrieval System's Database on 3-Buten-2-one, 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-, (E)- (127-41-3). Available from, as of June 15, 2015: https://npirspublic.ceris.purdue.edu/ppis/ Scent-Off Pellets (Baker's & 18 Corporation): Active ingredient: Oil of mustard 0.20%; Oil of citronella 1.20%; Oil of lemongrass 2.00%; Oil of orange 0.02%; Methyl salicylate 0.02%; Bergamot oil 0.11%; 3-Buten-2-one, 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-, (E)- 0.01%; and Geraniol 0.04%. 94 10 https://pubchem.ncbi.nlm.nih.gov/compound/citronella PubChem Internal Link CID-7794 158 17 https://pubchem.ncbi.nlm.nih.gov/compound/Methyl%20salicylate PubChem Internal Link CID-4133 203 13 https://pubchem.ncbi.nlm.nih.gov/compound/3-Buten-2-one PubChem Internal Link CID-6570 274 8 https://pubchem.ncbi.nlm.nih.gov/compound/Geraniol PubChem Internal Link CID-637566 26 PEER REVIEWED National Pesticide Information Retrieval System's Database on 3-Buten-2-one, 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-, (E)- (127-41-3). Available from, as of June 15, 2015: https://npirspublic.ceris.purdue.edu/ppis/ Scent-Off Aroma Pouches (Baker's & 18 Corporation): Active ingredient: Oil of mustard 0.20%; Oil of citronella 1.20%; Oil of lemongrass 2.00%; Oil of orange 0.02%; Methyl salicylate 0.02%; Bergamot oil 0.11%; 3-Buten-2-one, 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-, (E)- 0.01%; and Geraniol 0.04%. 100 10 https://pubchem.ncbi.nlm.nih.gov/compound/citronella PubChem Internal Link CID-7794 164 17 https://pubchem.ncbi.nlm.nih.gov/compound/Methyl%20salicylate PubChem Internal Link CID-4133 209 13 https://pubchem.ncbi.nlm.nih.gov/compound/3-Buten-2-one PubChem Internal Link CID-6570 280 8 https://pubchem.ncbi.nlm.nih.gov/compound/Geraniol PubChem Internal Link CID-637566

U.S. Production The amount of this chemical produced/manufactured in the U.S. 13 Aggregated Product Volume https://www.epa.gov/chemical-data-reporting 2019: 100,000 - <500,000 lb 2018: 100,000 - <500,000 lb 2017: 100,000 - <500,000 lb 2016: 100,000 - <500,000 lb 26 PEER REVIEWED USEPA/Pollution Prevention and Toxics; 2012 Chemical Data Reporting Database. 3-Buten-2-one, 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-, (3E)- (127-41-3). Available from, as of June 12, 2015: https://java.epa.gov/oppt_chemical_search/ Non-confidential 2012 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: 3-Buten-2-one, 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-, (3E)-. National Production Volume: Withheld. 162 13 https://pubchem.ncbi.nlm.nih.gov/compound/3-Buten-2-one PubChem Internal Link CID-6570

General Manufacturing Information General manufacturing information for this chemical, provided by the Hazardous Substances Data Bank (HSDB) and EPA TSCA Chemical Substance Inventory. Columns 13 Industry Processing Sectors Plastics Material and Resin Manufacturing All Other Chemical Product and Preparation Manufacturing Other (requires additional information) Soap, Cleaning Compound, and Toilet Preparation Manufacturing 14 EPA TSCA Commercial Activity Status 3-Buten-2-one, 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-, (3E)-: ACTIVE 0 13 https://pubchem.ncbi.nlm.nih.gov/compound/3-Buten-2-one PubChem Internal Link CID-6570 26 PEER REVIEWED Sells CS; Terpenoids. Kirk-Othmer Encyclopedia of Chemical Technology (1999-2015). John Wiley & Sons, Inc. Online Posting Date: September 15, 2006 ... Alpha- and beta-ionones account for 57% of the volatile components of violet flowers (Viola odorata).

Safety and Hazards Information on safety and hazards for this compound, including safety/hazards properties, reactivity, incompatibilities, management techniques, first aid treatments, and more. For toxicity and related information, please see the Toxicity section.

Hazards Identification This section identifies the hazards of the chemical presented on the safety data sheet (SDS) and the appropriate warning information associated with those hazards. The information in this section includes, but are not limited to, the hazard classification of the chemical, signal word, pictograms, hazard statements and precautionary statements. https://www.osha.gov/sites/default/files/publications/OSHA3514.pdf

GHS Classification GHS (Globally Harmonized System of Classification and Labelling of Chemicals) is a United Nations system to identify hazardous chemicals and to inform users about these hazards. GHS has been adopted by many countries around the world and is now also used as the basis for international and national transport regulations for dangerous goods. The GHS hazard statements, class categories, pictograms, signal words, and the precautionary statements can be found on the PubChem GHS page. https://pubchem.ncbi.nlm.nih.gov/ghs/ ThisSection 2 Name Value 1 17 GHS Hazard Statements Not Classified Reported as not meeting GHS hazard criteria by 1609 of 1735 companies (only ~ 7.3% companies provided GHS information). For more detailed information, please visit ECHA C&L website. 165 20 https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/78026 25 Pictogram(s) 0 1 https://pubchem.ncbi.nlm.nih.gov/images/ghs/GHS07.svg Icon Irritant 25 Signal Warning 0 7 Color GHSWarning 25 GHS Hazard Statements H315: Causes skin irritation [Warning Skin corrosion/irritation] 30 7 Color GHSWarning H317: May cause an allergic skin reaction [Warning Sensitization, Skin] 43 7 Color GHSWarning 25 Precautionary Statement Codes P261, P264, P272, P280, P302+P352, P321, P332+P317, P333+P317, P362+P364, and P501 (The corresponding statement to each P-code can be found at the GHS Classification page.) 64 18 https://pubchem.ncbi.nlm.nih.gov/ghs/#_prec 26 Pictogram(s) 0 1 https://pubchem.ncbi.nlm.nih.gov/images/ghs/GHS08.svg Icon Health Hazard 26 Signal Danger 0 6 Color GHSDanger 26 GHS Hazard Statements H334: May cause allergy or asthma symptoms or breathing difficulties if inhaled [Danger Sensitization, respiratory] 81 6 Color GHSDanger 26 Precautionary Statement Codes P233, P260, P271, P284, P304+P340, P342+P316, P403, and P501 (The corresponding statement to each P-code can be found at the GHS Classification page.) 64 18 https://pubchem.ncbi.nlm.nih.gov/ghs/#_prec

Hazard Classes and Categories The Hazard Classes and Categories are aligned with GHS (Globally Harmonized System of Classification and Labelling of Chemicals) hazard statement codes. The percentage data in the parenthesis from ECHA indicates that the hazard classes and categories information are consolidated from multiple companies. Also, see the detailed explanation from the above GHS classification section. https://pubchem.ncbi.nlm.nih.gov/ghs/ 2 17 Not Classified 25 Skin irritation - category 2 Skin sensitisation - category 1

NFPA Hazard Classification The National Fire Protection Association (NFPA) Hazard Classification (also known as NFPA 704) provides a simple, readily recognized, easily understood system for identifying the specific hazards of a material and the severity of the hazard that would occur during an emergency response. The system addresses the health, flammability, instability, and special hazards presented from short-term, acute exposures that could occur as a result of a fire, spill, or similar emergency. https://www.nfpa.org/News-and-Research/Publications-and-media/Blogs-Landing-Page/NFPA-Today/Blog-Posts/2021/11/05/Hazardous-Materials-Identification ThisSection 2 Name Value 1 26 NFPA 704 Diamond 0 1 https://pubchem.ncbi.nlm.nih.gov/image/nfpa.cgi?code=010 Icon 0-1-0 26 NFPA Health Rating 0 - Materials that, under emergency conditions, would offer no hazard beyond that of ordinary combustible materials. 26 NFPA Fire Rating 1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur. 26 NFPA Instability Rating 0 - Materials that in themselves are normally stable, even under fire conditions.

Skin, Eye, and Respiratory Irritations Skin, eye and respiratory irritations caused by exposure to this chemical. 26 PEER REVIEWED Lalko J et al; Food Chem Toxicol 45 Suppl 1: S235-40 (2007) alpha-Ionone was found to be a moderate /skin/ irritant. 0 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-Ionone PubChem Internal Link CID-5282108

Fire Fighting This section provides fire fighting information, including fire fighting procedures and hazards.

Fire Fighting Procedures This section provides information on the actions to be taken in the event of a fire emergency involving this chemical, to prevent the spread of and extinguish fires. 26 PEER REVIEWED Sigma-Aldrich; Safety Data Sheet for alpha-Ionone. Product Number: I12409, Version 4.6 (Revision Date 07/09/2014). Available from, as of July 10, 2015: https://www.sigmaaldrich.com/safety-center.html Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. 34 5 https://pubchem.ncbi.nlm.nih.gov/compound/water PubChem Internal Link CID-962 87 14 https://pubchem.ncbi.nlm.nih.gov/compound/carbon%20dioxide PubChem Internal Link CID-280 26 PEER REVIEWED Sigma-Aldrich; Safety Data Sheet for alpha-Ionone. Product Number: I12409, Version 4.6 (Revision Date 07/09/2014). Available from, as of July 10, 2015: https://www.sigmaaldrich.com/safety-center.html Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary. 26 PEER REVIEWED National Fire Protection Association; Fire Protection Guide to Hazardous Materials. 14TH Edition, Quincy, MA 2010, p. 325-74 Extinguishing methods: Alcohol foam. Water or foam may cause frothing. 37 5 https://pubchem.ncbi.nlm.nih.gov/compound/Water PubChem Internal Link CID-962

Accidental Release Measures This section provides recommendations on the appropriate response to spills, leaks, or releases, including containment and cleanup practices to prevent or minimize exposure to people, properties, or the environment. It may also include recommendations distinguishing between responses for large and small spills where the spill volume has a significant impact on the hazard. https://www.osha.gov/sites/default/files/publications/OSHA3514.pdf

Cleanup Methods Procedures for cleanup of chemical spill or hazardous waste 26 PEER REVIEWED Sigma-Aldrich; Safety Data Sheet for alpha-Ionone. Product Number: I12409, Version 4.6 (Revision Date 07/09/2014). Available from, as of July 10, 2015: https://www.sigmaaldrich.com/safety-center.html ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas.; Environmental precautions: Do not let product enter drains.; Methods and materials for containment and cleaning up: Soak up with inert absorbent material and dispose of as hazardous waste. Keep in suitable, closed containers for disposal.

Disposal Methods Disposal methods or procedures for this chemical or hazardous waste containing it. 26 PEER REVIEWED SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. 238 5 https://pubchem.ncbi.nlm.nih.gov/compound/water PubChem Internal Link CID-962 26 PEER REVIEWED Sigma-Aldrich; Safety Data Sheet for alpha-Ionone. Product Number: I12409, Version 4.6 (Revision Date 07/09/2014). Available from, as of July 10, 2015: https://www.sigmaaldrich.com/safety-center.html Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. Contaminated packaging: Dispose of as unused product.

Preventive Measures Preventive measures to take to avoid suffering negative health effects from this chemical. 26 PEER REVIEWED Sigma-Aldrich; Safety Data Sheet for alpha-Ionone. Product Number: I12409, Version 4.6 (Revision Date 07/09/2014). Available from, as of July 10, 2015: https://www.sigmaaldrich.com/safety-center.html Precautions for safe handling: Avoid contact with skin and eyes. Avoid inhalation of vapor or mist. Normal measures for preventive fire protection. 26 PEER REVIEWED Sigma-Aldrich; Safety Data Sheet for alpha-Ionone. Product Number: I12409, Version 4.6 (Revision Date 07/09/2014). Available from, as of July 10, 2015: https://www.sigmaaldrich.com/safety-center.html Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. 26 PEER REVIEWED Sigma-Aldrich; Safety Data Sheet for alpha-Ionone. Product Number: I12409, Version 4.6 (Revision Date 07/09/2014). Available from, as of July 10, 2015: https://www.sigmaaldrich.com/safety-center.html Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.

Handling and Storage This section provides guidance on the safe handling practices and storage conditions for this chemical. The information in this section includes precautions for safe handling, such as recommendations for handling incompatible chemicals, minimizing the release of the chemical into the environment, and providing advice on general hygiene practices (e.g., eating, drinking, and smoking in work areas is prohibited). In addition, this section provides recommendations on the conditions for safe storage (including any incompatibilities) as well as advice on specific storage requirements (e.g., ventilation requirements). https://www.osha.gov/sites/default/files/publications/OSHA3514.pdf

Storage Conditions Conditions for safe storage of this compound, including any incompatible chemicals and specific storage requirements (e.g., ventilation requirements). 26 PEER REVIEWED Sigma-Aldrich; Safety Data Sheet for alpha-Ionone. Product Number: I12409, Version 4.6 (Revision Date 07/09/2014). Available from, as of July 10, 2015: https://www.sigmaaldrich.com/safety-center.html Conditions for safe storage, including any incompatibilities: Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. Light sensitive.

Exposure Control and Personal Protection This section provides information on the exposure limits, engineering controls, and personal protective measures that can be used to minimize worker exposure. The information in this section includes OSHA Permissible Exposure Limits (PELs), American Conference of Governmental Industrial Hygienists (ACGIH) Threshold Limit Values (TLVs), and any other exposure limit used or recommended by the chemical manufacturer, importer, or employer preparing the safety data sheet, where available. In addition, this section contains information on appropriate engineering controls (e.g., use local exhaust ventilation, or use only in an enclosed system) as well as recommendations for personal protective measures to prevent illness or injury from exposure to chemicals, such as personal protective equipment (PPE) (e.g., appropriate types of eye, face, skin or respiratory protection needed based on hazards and potential exposure). https://www.osha.gov/sites/default/files/publications/OSHA3514.pdf

Personal Protective Equipment (PPE) Personal protective equipment (PPE) to use when handling this chemical. 26 PEER REVIEWED Sigma-Aldrich; Safety Data Sheet for alpha-Ionone. Product Number: I12409, Version 4.6 (Revision Date 07/09/2014). Available from, as of July 10, 2015: https://www.sigmaaldrich.com/safety-center.html Eye/face protection: Face shield and safety glasses. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). 26 PEER REVIEWED Sigma-Aldrich; Safety Data Sheet for alpha-Ionone. Product Number: I12409, Version 4.6 (Revision Date 07/09/2014). Available from, as of July 10, 2015: https://www.sigmaaldrich.com/safety-center.html Skin protection: Handle with gloves. 26 PEER REVIEWED Sigma-Aldrich; Safety Data Sheet for alpha-Ionone. Product Number: I12409, Version 4.6 (Revision Date 07/09/2014). Available from, as of July 10, 2015: https://www.sigmaaldrich.com/safety-center.html Body Protection: Complete suit protecting against chemicals. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. 26 PEER REVIEWED Sigma-Aldrich; Safety Data Sheet for alpha-Ionone. Product Number: I12409, Version 4.6 (Revision Date 07/09/2014). Available from, as of July 10, 2015: https://www.sigmaaldrich.com/safety-center.html Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multipurpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

Stability and Reactivity This section describes the stability and reactivity hazards of the chemical. For some compounds, related information may also be found in the "Stability/Shelf Life" section under Experimental Properties (if available). https://www.osha.gov/sites/default/files/publications/OSHA3514.pdf

Hazardous Reactivities and Incompatibilities This compound may undergo hazardous reactions with other chemicals. Therefore, it is considered incompatible with those chemicals and should not be used with them. 26 PEER REVIEWED Sigma-Aldrich; Safety Data Sheet for alpha-Ionone. Product Number: I12409, Version 4.6 (Revision Date 07/09/2014). Available from, as of July 10, 2015: https://www.sigmaaldrich.com/safety-center.html Incompatible materials: Strong oxidizing agents.

Regulatory Information This section lists the regulations related to the safety, health, and environment of the chemical and its associated products. The regulatory information, which may encompass national and/or regional regulations pertaining to the chemical or mixtures, is presented solely for informational purposes. For additional details, please consult the links to the information sources provided under each data entry. 18 REACH Registered Substance Status: Active Update: 25-07-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/18612 34 70 https://echa.europa.eu/registration-dossier/-/registered-dossier/18612 44 New Zealand EPA Inventory of Chemical Status alpha-Ionone: Does not have an individual approval but may be used under an appropriate group standard 0 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-Ionone PubChem Internal Link CID-5282108

FDA Requirements FDA requirements regarding this chemical and products containing it. FDA Requirements means any requirements of the Federal Food, Drug and Cosmetic Act (FDCA), as amended, and any rules or regulations promulgated thereunder which are or may be applicable to the manufacture, sale, labeling or distribution of the products regulated by FDA (e.g., drugs, biologics, dietary supplements, foods, cosmetics, tobacco products, etc.). https://www.fda.gov/regulatory-information/laws-enforced-fda/federal-food-drug-and-cosmetic-act-fdc-act 26 PEER REVIEWED 21 CFR 172.515 (USFDA); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of June 12, 2015: https://www.ecfr.gov alpha-Ionone is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and b) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part. 0 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-Ionone PubChem Internal Link CID-5282108

Other Safety Information Miscellaneous safety information for this chemical that is not shown in other sections, such as history, incidents, special reports, and so on.

Toxic Combustion Products Toxic products (e.g., gases and vapors) produced from the combustion of this chemical. 26 PEER REVIEWED Sigma-Aldrich; Safety Data Sheet for alpha-Ionone. Product Number: I12409, Version 4.6 (Revision Date 07/09/2014). Available from, as of July 10, 2015: https://www.sigmaaldrich.com/safety-center.html Special hazards arising from the substance or mixture: Carbon oxides

Toxicity Toxicity information related to this compound, including routes of exposure, related symptoms, acute and chronic effects, and numerical measures of toxicity.

Toxicological Information This section provides toxicological and health effects information for the chemical. It includes the likely routes of exposure (inhalation, ingestion, skin and eye contact), and the delayed, immediate, or chronic effects/symptoms from short- and long-term exposure, and the numerical measures of toxicity [e.g., acute toxicity estimates such as the LD50 (median lethal dose, the estimated amount of a chemical expected to kill 50% of test animals in a single dose)]. This section also includes information on whether the chemical is considered as a potential carcinogen according to authoritative sources such as the National Toxicology Program (NTP) Report on Carcinogens and the International agency for Research on Cancer (IARC) Monographs.

Toxicity Summary Summary of the toxicity of this compound, provided by the Hazardous Substances Data Bank (HSDB) and other sources. 26 PEER REVIEWED IDENTIFICATION AND USE: Alpha-ionone (AI) is a colorless to slightly yellow liquid. AI is a fragrance ingredient in perfumery, in cosmetics and personal care products, in household cleaners and detergents. Flavoring agent in beverages, baked goods, and candies. Used as an ingredient in dog/cat repellent. It is registered for pesticide use in the USA but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses. HUMAN EXPOSURE AND TOXICITY: AI (32 % in acetone) was found to be a moderate irritant. No reactions were observed with 1% AI; 5% AI produced one irritant/questionable reaction. ANIMAL STUDIES: No skin irritation was observed in miniature swine using neat AI. In guinea pigs AI was reported to be moderately irritating in skin test. AI produced severe skin irritation reaction in rabbits. AI was tested in a 90-days oral toxicity study using male and female rats. Body weigh gains and feed intake were reduced slightly in both males and females (10 mg/kg). In rats diet containing mixture of AI (60%) and beta-ionone produced swelling of hepatic parenchymal cells after 17 weeks. No mutagenic activity was observed in Salmonella typhimurium strains TA98 and TA100 when treated with AI at concentrations up to approximately 50 ug/plate with and without metabolic activation. AI at 25 mM concentration caused significant increases in chromosome aberrations in Chinese hamster cells. A micronucleus test in mice was negative. 24 12 https://pubchem.ncbi.nlm.nih.gov/compound/Alpha-ionone PubChem Internal Link CID-5282108 536 7 https://pubchem.ncbi.nlm.nih.gov/compound/acetone PubChem Internal Link CID-180 1099 11 https://pubchem.ncbi.nlm.nih.gov/compound/beta-ionone PubChem Internal Link CID-638014

Carcinogen Classification This section provides the International Agency for Research on Cancer (IARC) Carcinogenic Classification and related monograph links. In the IARC Carcinogenic classification, chemicals are categorized into four groups: Group 1 (carcinogenic to humans), Group 2A (probably carcinogenic to humans), Group 2B (possibly carcinogenic to humans), and Group 3 (not classifiable as to its carcinogenicity to humans). https://monographs.iarc.who.int/agents-classified-by-the-iarc/ ThisSection 2 Name Value 72 No indication of carcinogenicity to humans (not listed by IARC).

Acute Effects The results from acute animal tests and/or acute human studies are presented in this section. Acute animal studies consist of LD50 and LC50 tests, which present the median lethal dose (or concentration) to the animals. Acute human studies usually consist of case reports from accidental poisonings or industrial accidents. These case reports often help to define the levels at which acute toxic effects are seen in humans. 8 chemidplus

Antidote and Emergency Treatment Information on antidote and emergency treatment when exposed to this chemical. The information here is from the Hazardous Substances Data Bank (HSDB). https://pubchem.ncbi.nlm.nih.gov/source/11933 26 PEER REVIEWED Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3rd revised edition, Elsevier Mosby, St. Louis, MO 2007, p. 160 /SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/ 324 5 https://pubchem.ncbi.nlm.nih.gov/compound/water PubChem Internal Link CID-962 26 PEER REVIEWED Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3rd revised edition, Elsevier Mosby, St. Louis, MO 2007, p. 160 /SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/ 216 6 https://pubchem.ncbi.nlm.nih.gov/element/Oxygen PubChem Internal Link Element-Oxygen 468 5 https://pubchem.ncbi.nlm.nih.gov/compound/water PubChem Internal Link CID-962 637 5 https://pubchem.ncbi.nlm.nih.gov/compound/water PubChem Internal Link CID-962 26 PEER REVIEWED Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3rd revised edition, Elsevier Mosby, St. Louis, MO 2007, p. 160-1 /SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W TKO /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/ 378 9 https://pubchem.ncbi.nlm.nih.gov/compound/albuterol PubChem Internal Link CID-2083 775 8 https://pubchem.ncbi.nlm.nih.gov/compound/diazepam PubChem Internal Link CID-3016 787 9 https://pubchem.ncbi.nlm.nih.gov/compound/lorazepam PubChem Internal Link CID-3958 807 26 https://pubchem.ncbi.nlm.nih.gov/compound/proparacaine%20hydrochloride PubChem Internal Link CID-517321

Human Toxicity Excerpts Excerpts about human toxicity of this compound, extracted from authoritative documents, such as journal articles, government reports, and reference books. 26 PEER REVIEWED Lalko J et al; Food Chem Toxicol 45 Suppl 1: S235-40 (2007) /HUMAN EXPOSURE STUDIES/ A 48-hr occluded patch test was conducted on the backs of 50 adult male volunteers. A 0.05 g aliquot of 32% alpha-ionone in acetone was placed on 15 mm patches which were then applied to the back of each subject for 48 hr. The patches were removed and the sites were swabbed with dry gauze to remove residual test material. Reactions were evaluated at 30 min after patch removal and if necessary, at 72, 96 and 120 hr after patch removal. alpha-ionone was found to be a moderate irritant. 133 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 149 7 https://pubchem.ncbi.nlm.nih.gov/compound/acetone PubChem Internal Link CID-180 464 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 26 PEER REVIEWED Lalko J et al; Food Chem Toxicol 45 Suppl 1: S235-40 (2007) /HUMAN EXPOSURE STUDIES/ In a multicenter study, /researchers/ reported the results of patch tests with 48 fragrance materials. alpha-Ionone at 1% and 5% in petrolatum was tested in 86 male and 119 female patients. alpha-Ionone was applied to the back for 48 hr using Finn chambers on Scanpor tape. Reactions were assessed per ICDRG /(International Contact Dermatitis Research Group)/ guidelines on days 2 and 3 or on days 2 and 4. No reactions were observed with 1% alpha-ionone; 5% alpha-ionone produced one irritant/questionable reaction. 128 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-Ionone PubChem Internal Link CID-5282108 215 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-Ionone PubChem Internal Link CID-5282108 467 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 484 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108

Non-Human Toxicity Excerpts Excerpts about non-human toxicity of this compound, extracted from authoritative documents, such as journal articles, government reports, and reference books. 26 PEER REVIEWED Lalko J et al; Food Chem Toxicol 45 Suppl 1: S235-40 (2007) /LABORATORY ANIMALS: Acute Exposure/ ... A toxicity study was conducted in four groups of five male and five female ICR mice each. Each animal received a single intraperitoneal injection (2 mL/kg) of 1.2, 1.4, 1.6 or 1.8 g/kg alpha-ionone. Observations were made after dose administration and daily thereafter for 3 days. All animals died at 1.8 g/kg, 2/5 males and 3/5 females died at 1.6 g/kg, 2/5 males and all females died at 1.4 g/kg. Clinical signs included lethargy, piloerection, convulsions, hunched position and prostration. In addition, all mice at 1.4 g/kg had tremors. Based on these results, the high dose for the micronucleus test was set at 1.2 which was estimated to be the maximum tolerated dose. 226 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 26 PEER REVIEWED Lalko J et al; Food Chem Toxicol 45 Suppl 1: S235-40 (2007) /LABORATORY ANIMALS: Acute Exposure/ Six Pitman-Moore improved strain miniature swine received a single dermal application of 50 mg of neat alpha-ionone on the clipped dorsal skin for 48 hr under occlusion. After the 48-hr exposure period, the patches were removed, and the reactions were then evaluated. No irritation was observed. 140 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 26 PEER REVIEWED Lalko J et al; Food Chem Toxicol 45 Suppl 1: S235-40 (2007) /LABORATORY ANIMALS: Acute Exposure/ A 0.1 mL aliquot of neat alpha-ionone was applied to a 3 sq m area on the clipped dorsal skin of six male Hartley guinea pigs. Reactions were read 24 hr after application. After the reading, the hair on the test areas was clipped again and the test material was applied 30 min later. A second set of readings and applications were made 48 hr later. Following the 72-hr reading, all the hair on the dorsal surface of each animal was clipped and 40 mg/kg of Evans blue dissolved in physiological saline was injected intravenously into each animal. alpha-Ionone was reported to be moderately irritating in guinea pigs. 62 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 493 10 https://pubchem.ncbi.nlm.nih.gov/compound/Evans%20blue PubChem Internal Link CID-9409 583 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-Ionone PubChem Internal Link CID-5282108 26 PEER REVIEWED Lalko J et al; Food Chem Toxicol 45 Suppl 1: S235-40 (2007) /LABORATORY ANIMALS: Acute Exposure/ A closed primary skin irritation test was conducted in albino Angora rabbits (6/group) weighing 2.3-3.0 kg. A 0.1 g of neat alpha-ionone was applied to the clipped dorsal skin of each animal. The animals were wrapped with a plastic collar around the neck for 24 hr. The collar was then removed and reactions were read. After reading, hair from the test area was clipped again and alpha-ionone was applied 30 min later. A second set of readings and applications was made 48 hr later. After the 72 hr reading, all hair on the dorsal surface of each animal was clipped. Each animal was injected intravenously with 40 mg/kg Evans blue dissolved in normal saline. One hour after the injection, the animals were killed by exsanguination and the dorsal skin was removed. The dilating rate of blood vessels, swelling rate, (edema), blueing rate (as a result of increased capillary permeability) and reddening rate (erythema) on the test site were observed. Total scores of the living skin and isolated skin were referred to as the primary irritation index. alpha-Ionone produced severe irritation reaction. 161 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 417 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 657 10 https://pubchem.ncbi.nlm.nih.gov/compound/Evans%20blue PubChem Internal Link CID-9409 681 13 https://pubchem.ncbi.nlm.nih.gov/compound/normal%20saline PubChem Internal Link CID-5234 1086 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-Ionone PubChem Internal Link CID-5282108 26 PEER REVIEWED For more Non-Human Toxicity Excerpts (Complete) data for alpha-Ionone (16 total), please visit the HSDB record page. 99 16 https://pubchem.ncbi.nlm.nih.gov/source/hsdb/8268#section=Non-Human-Toxicity-Excerpts-(Complete) 57 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-Ionone PubChem Internal Link CID-5282108

Non-Human Toxicity Values Quantitative non-human toxicity values (e.g., lethal dose) for this compound. The data shown here are mostly for lab animals (e.g., rat, mouse, guinea pig, and rabbit). 5 26 PEER REVIEWED WHO; WHO Food Additive Series 19. Ionone (1984). Available from as of July 15, 2015: https://www.inchem.org LD50 Mouse i.p 2,277 mg/kg 26 PEER REVIEWED WHO; WHO Food Additive Series 19. Ionone (1984). Available from as of July 15, 2015: https://www.inchem.org LD50 Mouse s.c 2,605 mg/kg

Ecological Information This section provides information to evaluate the environmental impact of the chemical if it were released to the environment. The information may include data from toxicity tests performed on aquatic and/or terrestrial organisms, where available (e.g., acute or chronic aquatic toxicity data for fish, algae, and crustaceans; toxicity data on birds, bees, and plants). This section also includes information on whether there is a potential for the chemical to persist or degrade in the environment either through biodegradation or other processes (such as oxidation or hydrolysis) as well as the concentration or amount of the chemical found in the environment (e.g., in plants, animals as well as in the atmosphere or water).

Environmental Fate/Exposure Summary This section summarizes the environmental fate/exposure of this chemical, including the natural and artificial sources of the chemical as a pollutant, its environmental fate, biodegradation, abiotic degradation, bioconcentration, etc. 26 PEER REVIEWED alpha-Ionone's production and use in perfumery and as a flavoring compound in foods may result in its release to the environment through various waste streams. Its use as a fragrance ingredient in perfumery, in cosmetics and personal care products, in household cleaners and detergents and as an ingredient in dog/cat repellent used on plants and lawn furniture will result in its direct release to the environment. alpha-Ionone has been identified as a component of tobacco smoke. alpha-Ionone occurs widely in plants, such as, in violets, blackberries, plums, and tobacco. If released to air, an estimated vapor pressure of 0.019 mm Hg at 25 °C indicates alpha-ionone will exist solely as a vapor in the atmosphere. Vapor-phase alpha-ionone will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 2.7 hours. alpha-Ionone is also degraded in the atmosphere by reaction with ozone and nitrate radicals. By analogy to beta-ionone, the half-lives for the reaction with ozone and nitrate are estimated to be 14 and 0.8 hours, respectively. The nitrate radical is the dominant atmospheric oxidant during the night-time in most atmospheric environments, therefore, night-time degradation appears to be a major fate process for alpha-ionone. alpha-Ionone absorbs at wavelengths >290 nm and, therefore, may be susceptible to direct photolysis by sunlight. If released to soil, alpha-ionone is expected to have low mobility based upon an estimated Koc of 670. Volatilization from moist soil surfaces is expected to be an important fate process based upon an estimated Henry's Law constant of 4.5X10-5 atm-cu m/mole. alpha-Ionone may volatilize from dry soil surfaces based upon its odor and vapor pressure. The biodegradability of alpha-ionone is expected to be analogous to beta-ionone which was found to be readily biodegradable by two OECD screening tests. Utilizing the OECD 301F test, 79% of the Theoretical BOD was reached in 4 weeks indicating that biodegradation is an important environmental fate process. beta-Ionone was also classified as readily biodegradable by the results of a CO2-evolution test where beta-ionone achieved 46% and 73% CO2 evolution after 7 and 28 days, respectively. If released into water, alpha-ionone is expected to adsorb to suspended solids and sediment based upon the estimated Koc. In a spiked river water die-away test, the analogous beta-ionone was degraded about 95% after 20 hours of incubation. Volatilization from water surfaces is expected to be an important fate process based upon this compound's estimated Henry's Law constant. Estimated volatilization half-lives for a model river and model lake are 31 hours and 13 days, respectively. An estimated BCF of 161 suggests the potential for bioconcentration in aquatic organisms is high. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions. Photooxidation may occur in surface waters exposed to sunlight. Occupational exposure to alpha-ionone may occur through inhalation and dermal contact with this compound at workplaces where alpha-ionone is produced or used. Monitoring and use data indicate that the general population may be exposed to alpha-ionone via inhalation of ambient air, ingestion of food and drinking water, and dermal contact with consumer products containing alpha-ionone. (SRC) 0 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-Ionone PubChem Internal Link CID-5282108 416 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-Ionone PubChem Internal Link CID-5282108 482 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-Ionone PubChem Internal Link CID-5282108 657 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 730 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 908 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-Ionone PubChem Internal Link CID-5282108 973 5 https://pubchem.ncbi.nlm.nih.gov/compound/ozone PubChem Internal Link CID-24823 983 7 https://pubchem.ncbi.nlm.nih.gov/compound/nitrate PubChem Internal Link CID-943 1015 11 https://pubchem.ncbi.nlm.nih.gov/compound/beta-ionone PubChem Internal Link CID-638014 1065 5 https://pubchem.ncbi.nlm.nih.gov/compound/ozone PubChem Internal Link CID-24823 1075 7 https://pubchem.ncbi.nlm.nih.gov/compound/nitrate PubChem Internal Link CID-943 1139 7 https://pubchem.ncbi.nlm.nih.gov/compound/nitrate PubChem Internal Link CID-943 1320 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 1334 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-Ionone PubChem Internal Link CID-5282108 1468 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 1706 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-Ionone PubChem Internal Link CID-5282108 1821 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 1865 11 https://pubchem.ncbi.nlm.nih.gov/compound/beta-ionone PubChem Internal Link CID-638014 2105 11 https://pubchem.ncbi.nlm.nih.gov/compound/beta-Ionone PubChem Internal Link CID-638014 2207 11 https://pubchem.ncbi.nlm.nih.gov/compound/beta-ionone PubChem Internal Link CID-638014 2306 5 https://pubchem.ncbi.nlm.nih.gov/compound/water PubChem Internal Link CID-962 2313 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 2429 5 https://pubchem.ncbi.nlm.nih.gov/compound/water PubChem Internal Link CID-962 2464 11 https://pubchem.ncbi.nlm.nih.gov/compound/beta-ionone PubChem Internal Link CID-638014 2549 5 https://pubchem.ncbi.nlm.nih.gov/compound/water PubChem Internal Link CID-962 3127 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 3227 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 3340 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 3415 5 https://pubchem.ncbi.nlm.nih.gov/compound/water PubChem Internal Link CID-962 3475 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108

Natural Pollution Sources Pollutants are emitted from a range of natural and man-made (artificial) sources. This section provides information on the natural sources of the compound as a pollutant. 26 PEER REVIEWED (1) Fahlbusch KG et al; Flavors and Fragrances. Ullmann's Encyclopedia of Industrial Chemistry. 7th ed. (1999-2015). New York, NY: John Wiley & Sons. Online Posting Date: Jan 15, 2003. (2) Sell CS; Terpenoids. Kirk-Othmer Encyclopedia of Chemical Technology. (1999-2015). New York, NY: John Wiley & Sons. Online Posting Date: Sep 15, 2006. Both optical isomers of alpha-ionone are found in nature(1). alpha-Ionone occurs widely in plants, such as, in violets, blackberries, plums, and tobacco(2). 24 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 61 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-Ionone PubChem Internal Link CID-5282108

Artificial Pollution Sources Pollutants are emitted from a range of natural and man-made (artificial) sources. This section provides information on the artificial sources of the compound as a pollutant. 26 PEER REVIEWED (1) Sell CS; Terpenoids. Kirk-Othmer Encyclopedia of Chemical Technology. (1999-2015). New York, NY: John Wiley & Sons. Online Posting Date: Sep 15, 2006. (2) Burdock GA, ed; Fenaroli's Handbook of Flavor Ingredients. 6th ed. Boca Raton, FL: CRC Press, p. 955 (2010) (3) O'Neil MJ, ed; The Merck Index. 15th ed., Cambridge, UK: Royal Society of Chemistry, p. 940 (2013) (4) USEPA/OPPTS; Floral Attractants, Repellents, and Insecticides Fact Sheet. 2004. Available from, as of Jul 14, 2015: https://www.epa.gov/opp00001/chem_search/reg_actions/registration/fs_G-105_25-Sep-00.pdf (5) Rodgman A, Perfetti TA; The Chemical Components of Tobacco and Tobacco Smoke, Second Edition. CRC Press, Taylor & Francis Group, Boca Raton, FL, p. 2086 (2013) alpha-Ionone's production and use in perfumery(1) and as a flavoring compound in foods(2) may result in its release to the environment through various waste streams(SRC). Its use as a fragrance ingredient in perfumery, in cosmetics and personal care products, in household cleaners and detergents(3) and as an ingredient in dog/cat repellent used on plants and lawn furniture(4) will result in its direct release to the environment(SRC). alpha-Ionone has been identified as a component of tobacco smoke(5). 0 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-Ionone PubChem Internal Link CID-5282108 438 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-Ionone PubChem Internal Link CID-5282108

Environmental Fate Environmental fate describes where this chemical goes when it gets out into the environment and how it might be chemically transformed in that process. This section may provide information on multiple types of environmental fates of the chemical (e.g., aquatic fate, terrestrial fate, and atmospheric fate). 26 PEER REVIEWED (1) Swann RL et al; Res Rev 85: 17-28 (1983) (2) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.11. Nov, 2012. Available from, as of July 15, 2015: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm (3) Ohe S; Computer Aided Data Book of Vapor Pressure. Data Book Publ. Co., Tokyo, Japan, p. 1671 (1976) (4) Etzweiler F et al; Anal Chem 67: 655-8 (1995) (5) O'Neil MJ, ed; The Merck Index. 15th ed., Cambridge, UK: Royal Society of Chemistry, p. 940 (2013) (6) OECD; SIDS Initial Assessment Report For SIAM 20, beta-Ionone (CAS 79-77-6), April 2004, UNEP Publications. Available from, as July 13, 2015: https://www.inchem.org/documents/sids/sids/79776.pdf (7) NIST; NIST Chemistry WebBook. beta-Ionone (14901-07-6). NIST Standard Reference Database No. 69, Sept 2013 Release. Washington, DC: US Sec Commerce. Available from, as of July 14, 2015: https://webbook.nist.gov TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 670(SRC), determined from a structure estimation method(2), indicates that alpha-ionone is expected to have low mobility in soil(SRC). Volatilization of alpha-ionone from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.5X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 0.019 mm Hg(3), and water solubility, 106 mg/L(4). alpha-Ionone, a perfumery compound with an odor(5), is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). The biodegradability of alpha-ionone is expected to be analogous to beta-ionone(SRC) which was found to be readily biodegradable by two OECD screening tests(6). A 79% of theoretical BOD using activated sludge in the OECD 301F test(6) suggests that biodegradation is an important environmental fate process in soil(SRC). beta-Ionone was also classified as readily biodegradable by the results of a CO2-evolution test where beta-ionone achieved 46% and 73% CO2 evolution after 7 and 28 days, respectively(6). By analogy to beta-ionone(7), alpha-ionone is expected to absorbs at wavelengths >290 nm and, therefore, may be susceptible to direct photolysis on soil surfaces exposed to sunlight(SRC). 156 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 234 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 446 5 https://pubchem.ncbi.nlm.nih.gov/compound/water PubChem Internal Link CID-962 477 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-Ionone PubChem Internal Link CID-5282108 641 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 685 11 https://pubchem.ncbi.nlm.nih.gov/compound/beta-ionone PubChem Internal Link CID-638014 937 11 https://pubchem.ncbi.nlm.nih.gov/compound/beta-Ionone PubChem Internal Link CID-638014 1039 11 https://pubchem.ncbi.nlm.nih.gov/compound/beta-ionone PubChem Internal Link CID-638014 1138 11 https://pubchem.ncbi.nlm.nih.gov/compound/beta-ionone PubChem Internal Link CID-638014 1154 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 26 PEER REVIEWED (1) Swann RL et al; Res Rev 85: 17-28 (1983) (2) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.11. Nov, 2012. Available from, as of July 15, 2015: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm (3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 7-4, 7-5, 15-1 to 15-29 (1990) (4) Ohe S; Computer Aided Data Book of Vapor Pressure. Data Book Publ. Co., Tokyo, Japan, p. 1671 (1976) (5) Etzweiler F et al; Anal Chem 67: 655-8 (1995) (6) Franke C et al; Chemosphere 29: 1501-14 (1994) (7) Griffin S et al; J Chromat A: 864: 221-8 (1999) (8) OECD; SIDS Initial Assessment Report For SIAM 20, beta-Ionone (CAS 79-77-6), April 2004, UNEP Publications; Available from, as July 13, 2015: https://www.inchem.org/documents/sids/sids/79776.pdf (9) Mill T; pp. 368 in Handbook of Property Estimation Methods for Chemicals. Boethling RS, Mackay D, eds. Boca Raton, FL: Lewis Publ (2000) AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 670(SRC), determined from a structure estimation method(2), indicates that alpha-ionone is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 4.5X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 0.019 mm Hg(4), and water solubility, 106 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 31 hours and 13 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 161(SRC), from its log Kow of 3.85(7) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is high(SRC). The biodegradability of alpha-ionone is expected to be analogous to beta-ionone(SRC) which was found to be readily biodegradable by two OECD screening tests(8). A 79% of theoretical BOD using activated sludge in the OECD 301F test(8) suggests that biodegradation is an important environmental fate process in water(SRC). beta-Ionone was also classified as readily biodegradable by the results of a CO2-evolution test where beta-ionone achieved 46% and 73% CO2 evolution after 7 and 28 days respectively(8). In a spiked river water die-away test, beta-ionone, at 6.28 ug/L, was degraded about 95% after 20 hours of incubation(8). alpha-Ionone is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). alpha-Ionone is an olefin and olefins in surface waters exposed to sunlight react with photo-oxidants (such as hydroxyl radicals, peroxy radicals and singlet oxygen) with a half-life on the order of 25 days(9). 152 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 246 5 https://pubchem.ncbi.nlm.nih.gov/compound/water PubChem Internal Link CID-962 406 5 https://pubchem.ncbi.nlm.nih.gov/compound/water PubChem Internal Link CID-962 842 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 886 11 https://pubchem.ncbi.nlm.nih.gov/compound/beta-ionone PubChem Internal Link CID-638014 1127 5 https://pubchem.ncbi.nlm.nih.gov/compound/water PubChem Internal Link CID-962 1139 11 https://pubchem.ncbi.nlm.nih.gov/compound/beta-Ionone PubChem Internal Link CID-638014 1241 11 https://pubchem.ncbi.nlm.nih.gov/compound/beta-ionone PubChem Internal Link CID-638014 1343 5 https://pubchem.ncbi.nlm.nih.gov/compound/water PubChem Internal Link CID-962 1364 11 https://pubchem.ncbi.nlm.nih.gov/compound/beta-ionone PubChem Internal Link CID-638014 1447 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-Ionone PubChem Internal Link CID-5282108 1604 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-Ionone PubChem Internal Link CID-5282108 1754 14 https://pubchem.ncbi.nlm.nih.gov/compound/singlet%20oxygen PubChem Internal Link CID-159832 26 PEER REVIEWED (1) Bidleman TF; Environ Sci Technol 22: 361-367 (1988) (2) Ohe S; Computer Aided Data Book of Vapor Pressure. Data Book Publ. Co., Tokyo, Japan, p. 1671 (1976) (3) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.11. Nov, 2012. Available from, as of July 15, 2015: (4) Forester CD et al; Atmos Environ 41: 8758-71 (2007) https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm (5) Harrison JC, Ham JE; Int J Chem Kinet 41: 629-41 (2009) (6) Geyer A et al; J Geophys Res 108: 4368 (2003) (7) NIST; NIST Chemistry WebBook. beta-Ionone (14901-07-6). NIST Standard Reference Database No. 69, Sept 2013 Release. Washington, DC: US Sec Commerce. Available from, as of July 14, 2015: https://webbook.nist.gov ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), alpha-ionone, which has an extrapolated vapor pressure of 0.019 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase alpha-ionone is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 2.7 hours(SRC), calculated from its rate constant of 1.5X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Vapor-phase alpha-ionone is also degraded in the atmosphere by reaction with ozone and nitrate radicals(SRC); the half-lives for these reaction in air are estimated to be 14 and 0.8 hours respectively(SRC), calculated from analogous measured rate constants for beta-ionone of 1.9X10-17 cu cm/molecule-sec at 24 °C for ozone(4) and 9.4X10-12 cu cm/molecule-sec at 24 °C for nitrate radicals(5). The nitrate radical (NO3) is the dominant atmospheric oxidant during the night-time in most atmospheric environments(6), therefore, night-time degradation appears to be a major fate process for alpha-ionone(SRC). By analogy to beta-ionone(SRC), which absorbs strongly at wavelengths >290 nm(7), alpha-ionone may be susceptible to direct photolysis by sunlight(SRC). 124 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 285 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 617 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 682 5 https://pubchem.ncbi.nlm.nih.gov/compound/ozone PubChem Internal Link CID-24823 692 7 https://pubchem.ncbi.nlm.nih.gov/compound/nitrate PubChem Internal Link CID-943 866 11 https://pubchem.ncbi.nlm.nih.gov/compound/beta-ionone PubChem Internal Link CID-638014 923 5 https://pubchem.ncbi.nlm.nih.gov/compound/ozone PubChem Internal Link CID-24823 978 7 https://pubchem.ncbi.nlm.nih.gov/compound/nitrate PubChem Internal Link CID-943 1003 7 https://pubchem.ncbi.nlm.nih.gov/compound/nitrate PubChem Internal Link CID-943 1193 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 1226 11 https://pubchem.ncbi.nlm.nih.gov/compound/beta-ionone PubChem Internal Link CID-638014 1294 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108

Environmental Biodegradation This section provides information on environmental biodegradation for this compound. Biodegradation is the breakdown of organic matter by microorganisms, such as bacteria and fungi. An important measure of biodegradability of wastewater is the biochemical oxygen demand (BOD), which is the amount of dissolved oxygen (DO) needed (i.e. demanded) by aerobic biological organisms to break down organic material present in a given water sample at certain temperature over a specific time period. 26 PEER REVIEWED (1) OECD; SIDS Initial Assessment Report For SIAM 20, beta-Ionone (CAS 79-77-6), April 2004, UNEP Publications. Available from, as July 13, 2015: https://www.inchem.org/documents/sids/sids/79776.pdf (2) US EPA; High Production Volume (HPV) Challenge Program. The HPV voluntary challenge chemical list. Robust summaries and test plans. Methyl ionone (mixture of isomers) CAS No. 1335-46-2. Washington, DC: US EPA, Off. Prevent. Pest. Tox. Subst., Pollut. Prevent. Toxics. Available from, as of July 14, 2015: https://www.epa.gov/HPV/pubs/summaries/ionederv/c13660rr.pdf AEROBIC: The biodegradability of alpha-ionone is expected to be analogous to beta-ionone(SRC). Using the OECD 301F method (manometric respirometry) with an activated sludge inoculum, beta-ionone, at 50 mg/L, reached 79% of its theoretical BOD in 28 days which classified the compound as readily biodegradable(1). beta-Ionone was also classified as readily biodegradable by the results of a CO2-evolution test where beta-ionone, at 10 mg/L, achieved 46% and 73% CO2 evolution after 7 and 28 days respectively(1). Another respirometry study reported 80% biodegradation of beta-ionone at 100 mg/L(2). In a spiked river water die-away test using water from the Murrumbidgee River, beta-ionone, at 6.28 ug/L, was degraded about 95% after 20 hours of incubation(1). Results of a modified MITI test (OECD 301C) reported 50% degradation of beta-ionone after 28 days (consistent with inherent biodegradability), but concentrations or inoculum were not reported(1). 33 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 77 11 https://pubchem.ncbi.nlm.nih.gov/compound/beta-ionone PubChem Internal Link CID-638014 183 11 https://pubchem.ncbi.nlm.nih.gov/compound/beta-ionone PubChem Internal Link CID-638014 313 11 https://pubchem.ncbi.nlm.nih.gov/compound/beta-Ionone PubChem Internal Link CID-638014 415 11 https://pubchem.ncbi.nlm.nih.gov/compound/beta-ionone PubChem Internal Link CID-638014 570 11 https://pubchem.ncbi.nlm.nih.gov/compound/beta-ionone PubChem Internal Link CID-638014 616 5 https://pubchem.ncbi.nlm.nih.gov/compound/water PubChem Internal Link CID-962 642 5 https://pubchem.ncbi.nlm.nih.gov/compound/water PubChem Internal Link CID-962 677 11 https://pubchem.ncbi.nlm.nih.gov/compound/beta-ionone PubChem Internal Link CID-638014 832 11 https://pubchem.ncbi.nlm.nih.gov/compound/beta-ionone PubChem Internal Link CID-638014

Environmental Abiotic Degradation Abiotic degradation is a process by which a chemical substance is broken down into smaller molecules by non-biotic means (e.g., hydrolysis, photolysis, and oxidation). 26 PEER REVIEWED (1) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.11. Nov, 2012. Available from, as of July 15, 2015: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm (2) Forester CD et al; Atmos Environ 41: 8758-71 (2007) (3) Harrison JC, Ham JE; Int J Chem Kinet 41: 629-41 (2009) (4) Atkinson R; Atmos Environ 34: 2063-101 (2000) (5) Geyer A et al; J Geophys Res 108: 4368 (2003) (6) NIST; NIST Chemistry WebBook. beta-Ionone (14901-07-6). NIST Standard Reference Database No. 69, Sept 2013 Release. Washington, DC: US Sec Commerce. Available from, as of July 14, 2015: https://webbook.nist.gov (7) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 7-4, 7-5 (1990) (8) Mill T; pp. 368 in Handbook of Property Estimation Methods for Chemicals. Boethling RS, Mackay D, eds. Boca Raton, FL: Lewis Publ (2000) The rate constant for the vapor-phase reaction of alpha-ionone with photochemically-produced hydroxyl radicals has been estimated as 1.5X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2.7 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of alpha-ionone with atmospheric ozone is expected to similar to the measured value for beta-ionone(SRC), 1.9X10-17 cu cm/molecule-sec at 24 °C(2); this corresponds to an atmospheric half-life of about 14 hours at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(1). The rate constant for the vapor-phase reaction of alpha-ionone with atmospheric nitrate radicals is expected to similar to the measured value for beta-ionone(SRC), 9.4X10-12 cu cm/molecule-sec at 24 °C(3); this corresponds to an atmospheric half-life of about 0.8 hours(SRC) at an atmospheric concentration of 2.5X10+8 nitrate radicals per cu cm(4). The nitrate radical (NO3) is the dominant atmospheric oxidant during the night-time in most atmospheric environments(5), therefore, night-time degradation appears to be a major fate process for alpha-ionone(SRC). By analogy to beta-ionone(SRC), which absorbs strongly at wavelengths >290 nm(6), alpha-ionone may be susceptible to direct photolysis by sunlight(SRC). alpha-Ionone is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(7). alpha-Ionone is an olefin and olefins in surface waters exposed to sunlight react with photo-oxidants (such as hydroxyl radicals, peroxy radicals and singlet oxygen) with a half-life on the order of 25 days(8). 50 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 404 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 434 5 https://pubchem.ncbi.nlm.nih.gov/compound/ozone PubChem Internal Link CID-24823 489 11 https://pubchem.ncbi.nlm.nih.gov/compound/beta-ionone PubChem Internal Link CID-638014 655 5 https://pubchem.ncbi.nlm.nih.gov/compound/ozone PubChem Internal Link CID-24823 735 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 765 7 https://pubchem.ncbi.nlm.nih.gov/compound/nitrate PubChem Internal Link CID-943 831 11 https://pubchem.ncbi.nlm.nih.gov/compound/beta-ionone PubChem Internal Link CID-638014 1004 7 https://pubchem.ncbi.nlm.nih.gov/compound/nitrate PubChem Internal Link CID-943 1039 7 https://pubchem.ncbi.nlm.nih.gov/compound/nitrate PubChem Internal Link CID-943 1229 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 1262 11 https://pubchem.ncbi.nlm.nih.gov/compound/beta-ionone PubChem Internal Link CID-638014 1330 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 1401 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-Ionone PubChem Internal Link CID-5282108 1558 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-Ionone PubChem Internal Link CID-5282108 1708 14 https://pubchem.ncbi.nlm.nih.gov/compound/singlet%20oxygen PubChem Internal Link CID-159832

Environmental Bioconcentration This section provides information on environmental bioconcentration for this compound. Bioconcentration is the accumulation of a chemical in or on an organism when the source of chemical is solely water. Bioconcentration is a term that was created for use in the field of aquatic toxicology. Bioconcentration can also be defined as the process by which a chemical concentration in an aquatic organism exceeds that in water as a result of exposure to a waterborne chemical. 26 PEER REVIEWED (1) Griffin S et al; J Chromat A: 864: 221-8 (1999) (2) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.11. Nov, 2012. Available from, as of July 15, 2015: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm (3) Franke C et al; Chemosphere 29: 1501-14 (1994) An estimated BCF of 161 was calculated in fish for alpha-ionone(SRC), using a log Kow of 3.85(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC), provided the compound is not metabolized by the organism(SRC). 51 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108

Soil Adsorption/Mobility Sorption to soils and sediments is an important factor on the transport and fate of organic contaminants in the environment. The soil/water adsorption coefficient, also known as solid-water distribution coefficient (Kd), measures the amount of chemical substance adsorbed onto soil per amount of water. Since adsorption occurs predominantly by partition into the soil organic matter, it is more useful to normalize the Kd value to the organic carbon content of a soil and express the distribution coefficient in Koc (organic carbon normalized distribution coefficient). The greater the Kd (or Koc) value, the less likely a chemical will leach or contribute to runoff. A very high value means it is strongly adsorbed onto soil and organic matter and does not move throughout the soil. https://toxics.usgs.gov/pubs/FS-087-00/fs-087-00.pdf 26 PEER REVIEWED (1) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.11. Nov, 2012. Available from, as of July 15, 2015: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm (2) Swann RL et al; Res Rev 85: 17-28 (1983) Using a structure estimation method based on molecular connectivity indices(1), the Koc of alpha-ionone can be estimated to be 670(SRC). According to a classification scheme(2), this estimated Koc value suggests that alpha-ionone is expected to have low mobility in soil. 91 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 217 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108

Volatilization from Water/Soil Volatilization of chemicals from water/soil is the transfer of the chemical as a gas through the water-air or soil-air interface under environmental conditions 26 PEER REVIEWED (1) Ohe S; Computer Aided Data Book of Vapor Pressure. Data Book Publ. Co., Tokyo, Japan, p. 1671 (1976) (2) Etzweiler F et al; Anal Chem 67: 655-8 (1995) (3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 15-1 to 15-29 (1990) (4) O'Neil MJ, ed; The Merck Index. 15th ed., Cambridge, UK: Royal Society of Chemistry, p. 940 (2013) The Henry's Law constant for alpha-ionone is estimated as 4.5X10-5 atm-cu m/mole(SRC) derived from its extrapolated vapor pressure, 0.019 mm Hg(1), and water solubility, 106 mg/L(2). This Henry's Law constant indicates that alpha-ionone is expected to volatilize from water surfaces(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 31 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 13 days(SRC). alpha-Ionone's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). alpha-Ionone, a perfumery compound with an odor(4), is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1). 29 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 152 5 https://pubchem.ncbi.nlm.nih.gov/compound/water PubChem Internal Link CID-962 224 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 268 5 https://pubchem.ncbi.nlm.nih.gov/compound/water PubChem Internal Link CID-962 598 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-Ionone PubChem Internal Link CID-5282108 715 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-Ionone PubChem Internal Link CID-5282108

Environmental Water Concentrations Concentrations of this chemical in water in various stages of hydrologic cycle (e.g., drinking water, ground water, surface water, and rain/snow). 26 PEER REVIEWED (1) Guardiola J et al; Water Supply 7: 11-16 (1989) GROUNDWATER: Groundwater sampled from a contaminated industrial site in Spain contained ionone (isomers not specified) concentrations of 28-655 ng/L(1).

Sediment/Soil Concentrations Concentrations of this compound in sediment/soil. 26 PEER REVIEWED (1) Schwarzbauer J et al; Organic Geochemistry 31: 1713-31 (2000) SEDIMENT: alpha-Ionone was qualitatively detected in sediment collected in the German Bight, near the Elbe River, in 1998(1). 10 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-Ionone PubChem Internal Link CID-5282108

Food Survey Values Information on the amount or concentration of this compound in food, reported from various data sources. 26 PEER REVIEWED (1) Burdock GA, ed; Fenaroli's Handbook of Flavor Ingredients. 6th ed. Boca Raton, FL: CRC Press, p. 955 (2010) (2) Buttery RG et al; J Agric Food Chem 45: 837-43 (1997) In addition to a variety of fruits, alpha-ionone has detected in peas, cognac, rum, whiskies, white wines, tea, beans, buck wheat, and brandy(1). alpha-Ionone was detected in popcorn at a concentration of 2 ug/kg(2). 36 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 146 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-Ionone PubChem Internal Link CID-5282108

Plant Concentrations Concentrations of this compound in plants. 26 PEER REVIEWED (1) Sell CS; Terpenoids. Kirk-Othmer Encyclopedia of Chemical Technology. (1999-2015). New York, NY: John Wiley & Sons. Online Posting Date: Sep 15, 2006. (2) Burdock GA, ed; Fenaroli's Handbook of Flavor Ingredients. 6th ed. Boca Raton, FL: CRC Press, p.955 (2010) (3) Gomez E et al; J Agric Food Chem 41: 1669-76 (1993) (4) Guadayol JM et al; J Agric Food Chem 45: 1868-72 (1997) alpha- and beta-Ionone account for 57% of the volatile components of violet flowers (Viola odorata)(1). alpha-Ionone is reported to occur in apricot, orange peel oil, grapefruit juice, raspberry, blackberry, carrot, celery leaves and seed, peas, tomato, tea, beans,and loganberry(2). Apricots (Prunus armeniaca L.) were found to contain alpha-ionone at a concentration of 10 ug/kg of fresh fruit tissue(3). alpha-Ionone was detected in paprika oleoresin at a concentration of 0.4 mg/kg(4). 11 11 https://pubchem.ncbi.nlm.nih.gov/compound/beta-Ionone PubChem Internal Link CID-638014 104 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-Ionone PubChem Internal Link CID-5282108 337 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 407 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-Ionone PubChem Internal Link CID-5282108 26 PEER REVIEWED (1) USDA; Dr. Duke's Phytochemical and Ethnobotanical Databases. Plants with a chosen chemical. alpha-Ionone. Washington, DC: US Dept Agric, Agric Res Service. Available from, as of July 16, 2015: https://www.ars-grin.gov/duke/ alpha-Ionone detections in plants(1).[Table#8258] 37 12 Inline Table [Table#8258] 0 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-Ionone PubChem Internal Link CID-5282108 26 [Table#8258] IkdlbnVzIHNwZWNpZXMiLCJGYW1pbHkiLCJDb21tb24gbmFtZSIsIlBhcnQiLCJDb25jbiAocHBt KSIKIkNhbWVsbGlhIHNpbmVuc2lzIChMLikgS1VOVFpFIiwiVGhlYWNlYWUiLCJUZWEiLCJTaG9v dCIsIjUwMCIKIkhhbWFtZWxpcyB2aXJnaW5pYW5hIEwuIiwiSGFtYW1lbGlkYWNlYWUiLCJXaXRj aCBIYXplbCIsIkxlYWYiLCIxNzUiCiJMYXdzb25pYSBpbmVybWlzIEwuIiwiTHl0aHJhY2VhZSIs Ikhlbm5hLCBKYW1haWNhLU1pZ25vbmV0dGUsIE1pZ25vbmV0dGUgVHJlZSIsIkZsb3dlciIsIjQw IgoiQWNhY2lhIGZhcm5lc2lhbmEgKEwuKSBXSUxMRC4iLCJGYWJhY2VhZSIsIkNhc3NpZSwgSHVp c2FjaGUsIE9wb3BhbmF4LCBQb3BpbmFjLCBTd2VldCBBY2FjaWEiLCJGbG93ZXIiLCJub3QgcmVw b3J0ZWQiCiJBcGl1bSBncmF2ZW9sZW5zIEwuIiwiQXBpYWNlYWUiLCJDZWxlcnkiLCJQbGFudCIs Im5vdCByZXBvcnRlZCIKIkNpdHJ1cyBhdXJhbnRpdW0gTC4iLCJSdXRhY2VhZSIsIkJpdHRlciBP cmFuZ2UsIFBldGl0Z3JhaW4iLCJQbGFudCIsIm5vdCByZXBvcnRlZCIKIkRhdWN1cyBjYXJvdGEg TC4iLCJBcGlhY2VhZSIsIkNhcnJvdCIsIlJvb3QiLCJub3QgcmVwb3J0ZWQiCiJHaW5rZ28gYmls b2JhIEwuIiwiR2lua2dvYWNlYWUiLCJHaW5rZ28sIE1haWRlbmhhaXIgVHJlZSIsIldvb2QiLCJu b3QgcmVwb3J0ZWQiCiJTYXVzc3VyZWEgbGFwcGEgQy4gQi4gQ0xBUktFIiwiQXN0ZXJhY2VhZSIs IkNvc3R1cywgS3V0aCIsIlJvb3QiLCJub3QgcmVwb3J0ZWQiCiJWaW9sYSBvZG9yYXRhIEwuIiwi VmlvbGFjZWFlIiwiQ29tbW9uIFZpb2xldCwgU3dlZXQgVmlvbGV0IiwiRmxvd2VyIiwibm90IHJl cG9ydGVkIgo= text/csv

Other Environmental Concentrations Other environmental concentrations reported for this chemical. 26 PEER REVIEWED (1) Rodgman A, Perfetti TA; The Chemical Components of Tobacco and Tobacco Smoke, 2nd ed. Boca Raton, FL: CRC Press, Taylor & Francis Group, p. 2086 (2013) (2) National Toxicology Program. Testing Status of Agents at NTP. Bitter orange (Citrus auranantium var amara) Extracts and Constituents. June 2004. Available from, as of Jul 14, 2015: https://ntp.niehs.nih.gov/ntp/htdocs/chem_background/exsumpdf/bitterorange_508.pdf alpha-Ionone has been identified as a component of tobacco smoke(1). It is a component of bitter orange extract(2). 0 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-Ionone PubChem Internal Link CID-5282108

Probable Routes of Human Exposure Potential way(s) in which people may come into contact with a hazardous chemical. Examples of common exposure routes are inhalation, ingestion, skin/eye contact. 26 PEER REVIEWED (1) US EPA; Chemical Data Reporting (CDR). Non-confidential 2012 Chemical Data Reporting information on chemical production and use in the United States. Available from, as of July 10, 2015: https://www.epa.gov/cdr/pubs/guidance/cdr_factsheets.html According to the 2012 TSCA Inventory Update Reporting data, 4 reporting facilities estimate the number of persons reasonably likely to be exposed during the manufacturing, processing, or use of alpha-ionone (127-41-1) and ionone, mixed isomers (8013-90-9) may be as low as 10-24 workers up to the range of 50-99 workers per plant; the data may be greatly underestimated due to confidential business information (CBI) or unknown values(1). 22 4 https://pubchem.ncbi.nlm.nih.gov/compound/TSCA PubChem Internal Link CID-110408 194 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 26 PEER REVIEWED (1) NIOSH; NOES. National Occupational Exposure Survey conducted from 1981-1983. Estimated numbers of employees potentially exposed to specific agents by 2-digit standard industrial classification (SIC). Available from, as of July 10, 2015: https://www.cdc.gov/noes/ NIOSH (NOES Survey 1981-1983) has statistically estimated that 40,007 workers (11,154 of these were female) were potentially exposed to ionone (CAS 8013-90-9; mixed isomers) in the US(1). Occupational exposure to alpha-ionone may occur through inhalation and dermal contact with this compound at workplaces where alpha-ionone is produced or used. Monitoring and use data indicate that the general population may be exposed to alpha-ionone via inhalation of ambient air, ingestion of food and drinking water, and dermal contact with consumer products containing beta-ionone(SRC). 213 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 313 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 426 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108 501 5 https://pubchem.ncbi.nlm.nih.gov/compound/water PubChem Internal Link CID-962 561 11 https://pubchem.ncbi.nlm.nih.gov/compound/beta-ionone PubChem Internal Link CID-638014

Average Daily Intake The average amount of the compound taken into the body through eating, drinking, or breathing. 26 PEER REVIEWED (1) Burdock GA, ed; Fenaroli's Handbook of Flavor Ingredients. 6th ed. Boca Raton, FL: CRC Press, p.955 (2010) The individual daily intake for alpha-ionone has been reported as 0.002387 mg/kg/day(1). 32 12 https://pubchem.ncbi.nlm.nih.gov/compound/alpha-ionone PubChem Internal Link CID-5282108

Literature Scientific articles associated with this compound. Some chemical-literature associations in this section are provided by data contributors or derived from MeSH annotations, as explained in Kim et al., J. Cheminform. 2016, 8, 32. This section also provides the lists of chemicals, genes/proteins, and diseases, that are co-mentioned in scientific articles, as described in Zaslavsky et al., Front. Res. Metr. Anal., 2021, 6, 689059. https://pubchem.ncbi.nlm.nih.gov/docs/literature

Consolidated References The consolidated references include literature data from all sources including Springer Nature, Thieme Chemistry, Wiley, Nature journals, depositor provided citations, and NLM curated PubMed citations. https://pubchem.ncbi.nlm.nih.gov/docs/literature 75 literature

NLM Curated PubMed Citations The NLM Curated PubMed Citations section links to all PubMed records that are tagged with the same MeSH term that has been associated with a particular compound. https://jcheminf.biomedcentral.com/articles/10.1186/s13321-016-0142-6 75 https://www.ncbi.nlm.nih.gov/sites/entrez?LinkName=pccompound_pubmed_mesh&db=pccompound&cmd=Link&from_uid=5282108 true

Springer Nature References Literature references related to scientific contents from Springer Nature journals and books. These references have been ranked automatically by an algorithm which calculates the relevance for each substance in a Springer Nature document. It is based on: (1) the TF-IDF, adapted to chemical structures, (2) location information in the text (e.g. title, abstract, keywords), and (3) the document size. Springer Nature aims to provide only highly qualitative and relevant content but references of lower relevance aren't withheld as they might contain also very useful information. 70 springernature

Thieme References Literature references related to scientific contents from Thieme Chemistry journals and books. The Thieme Chemistry content within this section is provided under a CC-BY-NC-ND 4.0 license (https://creativecommons.org/licenses/by-nc-nd/4.0/), unless otherwise stated. 71 Thieme References ThiemeChemistry

Chemical Co-Occurrences in Literature Chemical co-occurrences in literature highlight chemicals mentioned together in scientific articles. This may suggest that an important relationship exists between the two. Please note that this content is not human curated. It is generated by text-mining algorithms that can be fooled such that a co-occurrence may be happenstance or a casual mention. The lists are ordered by relevancy as indicated by count of publications and other statistics, with the most relevant mentions appearing at the top. https://doi.org/10.3389/frma.2021.689059 75 Co-Occurrence Panel ChemicalNeighbor Chemical ChemicalName_1 ChemicalName_2 SUMMARY_URL.cid CID CID

Chemical-Gene Co-Occurrences in Literature Chemical-gene co-occurrences in the literature highlight chemical-gene pairs mentioned together in scientific articles. This may suggest that an important relationship exists between the two. Note that a co-occurring gene entity is organism non-specific and could refer to a gene, protein, or enzyme. Also note that this content is not human curated. It is generated by text-mining algorithms that can be fooled such that a co-occurrence may be happenstance or a casual mention. The lists are ordered by relevancy as indicated by count of publications and other statistics, with the most relevant mentions appearing at the top. https://doi.org/10.3389/frma.2021.689059 75 Co-Occurrence Panel ChemicalGeneSymbolNeighbor Gene/Protein/Enzyme ChemicalName GeneSymbolName https://pubchem.ncbi.nlm.nih.gov/gene/SYMBOL: CID GeneSymbol

Chemical-Disease Co-Occurrences in Literature Chemical-disease co-occurrences in literature highlight chemical-disease pairs mentioned together in scientific articles. This may suggest that an important relationship exists between the two. Please note that this content is not human curated. It is generated by text-mining algorithms that can be fooled such that a co-occurrence may be happenstance or a casual mention. The lists are ordered by relevancy as indicated by count of publications and other statistics, with the most relevant mentions appearing at the top. https://doi.org/10.3389/frma.2021.689059 75 Co-Occurrence Panel ChemicalDiseaseNeighbor Disease ChemicalName DiseaseName https://meshb.nlm.nih.gov/record/ui?ui= CID MeSH

Patents Patent applications/documents that mention this compound. Columns

Depositor-Supplied Patent Identifiers Patent identifiers provided by data depositors, along with information on those patents. 75 patent 75 Link to all deposited patent identifiers 0 40 https://pubchem.ncbi.nlm.nih.gov/rest/pug/compound/cid/5282108/xrefs/PatentID/TXT

WIPO PATENTSCOPE Use the provided link to show patents associated with this chemical structure in WIPO's PATENTSCOPE system. https://www.wipo.int/patentscope/en/ 91 Patents are available for this chemical structure: https://patentscope.wipo.int/search/en/result.jsf?inchikey=UZFLPKAIBPNNCA-BQYQJAHWSA-N 0 86 https://patentscope.wipo.int/search/en/result.jsf?inchikey=UZFLPKAIBPNNCA-BQYQJAHWSA-N

Chemical Co-Occurrences in Patents Chemical co-occurrences in patents highlight chemicals mentioned together in patent documents. This may suggest that an important relationship exists between the two. Please note that this content is not human curated. It is generated by text-mining algorithms that can be fooled such that a co-occurrence may be happenstance or a casual mention. The lists are ordered by relevancy as indicated by count of patents and other statistics, with the most relevant mentions appearing at the top. 75 Co-Occurrence Panel PatentChemicalChemical Chemical ChemicalName NeighborName SUMMARY_URL.cid CID CID

Chemical-Disease Co-Occurrences in Patents Disease co-occurrences in patents highlight chemicals and diseases mentioned together in patent documents. This may suggest that an important relationship exists between the two. Please note that this content is not human curated. It is generated by text-mining algorithms that can be fooled such that a co-occurrence may be happenstance or a casual mention. The lists are ordered by relevancy as indicated by count of patents and other statistics, with the most relevant mentions appearing at the top. 75 Co-Occurrence Panel PatentChemicalDisease Disease ChemicalName NeighborName https://meshb.nlm.nih.gov/record/ui?ui= CID MeSH

Chemical-Gene Co-Occurrences in Patents Gene co-occurrences in patents highlight chemicals and genes mentioned together in patent documents. This may suggest that an important relationship exists between the two. Please note that this content is not human curated. It is generated by text-mining algorithms that can be fooled such that a co-occurrence may be happenstance or a casual mention. The lists are ordered by relevancy as indicated by count of patents and other statistics, with the most relevant mentions appearing at the top. 75 Co-Occurrence Panel PatentChemicalGene Gene ChemicalName NeighborName https://pubchem.ncbi.nlm.nih.gov/gene/SYMBOL: CID GeneSymbol

Interactions and Pathways This section provides information on the biomolecular interactions of this compound with drugs, genes, proteins, etc., as well as the pathways in which this compound is involved.

Chemical-Target Interactions Interactions between targets and this compound 9 consolidatedcompoundtarget 72 consolidatedcompoundtarget

Biological Test Results A PubChem substance or compound summary page displays biological test results from the PubChem BioAssay database, if/as available, for the chemical structure currently displayed. You can embed biological test results displays within your own web pages, for a PubChem Compound or Substance of interest, by using the BioActivity Widget. https://pubchem.ncbi.nlm.nih.gov/docs/widgets

BioAssay Results Bioactivity data for this compound, reported in PubChem BioAssay records. 75 bioactivity

Taxonomy Organism-specific information about where this compound originated or is associated 38 The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106 consolidatedcompoundtaxonomy 43 consolidatedcompoundtaxonomy 73 consolidatedcompoundtaxonomy

Classification A set of concepts and categories in a subject area or domain that shows their properties and the relations between them.

MeSH Tree The Medical Subject Headings (MeSH) tree for this entity. MeSH is a controlled and hierarchically-organized vocabulary produced by the National Library of Medicine. https://www.nlm.nih.gov/mesh 77 HID https://pubchem.ncbi.nlm.nih.gov/classification/#hid=1 1

ChEBI Ontology ChEBI Ontology tree. ChEBI is an acronym for Chemical Entities of Biological Interest, which is a freely available dictionary of molecular entities focused on 'small' chemical compounds. ChEBI incorporates an ontological classification, whereby the relationships between molecular entities or classes of entities and their parents and/or children are specified. https://www.ebi.ac.uk/chebi/ 78 HID https://pubchem.ncbi.nlm.nih.gov/classification/#hid=2 2

KEGG: Phytochemical Compounds Phytochemical compounds classification/ontology tree from the Kyoto Encyclopedia of Genes and Genomes (KEGG). https://www.genome.jp/kegg-bin/get_htext?htext=br08003 79 HID https://pubchem.ncbi.nlm.nih.gov/classification/#hid=5 5

ChemIDplus Classification of this compound, provided by ChemIDplus, which is a free web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases. ChemIDplus groups chemicals based on the source locators (i.e., what information resources have data for a given chemical). https://chem.nlm.nih.gov/chemidplus/ 82 HID https://pubchem.ncbi.nlm.nih.gov/classification/#hid=84 84

ChEMBL Target Tree Classification of this entity in the context of targets, provided by ChEMBL. https://www.ebi.ac.uk/chembl/ 83 HID https://pubchem.ncbi.nlm.nih.gov/classification/#hid=87 87

UN GHS Classification The United Nations' Globally Harmonized System of Classification and Labelling of Chemicals (GHS) provides a harmonized basis for globally uniform physical, environmental, and health and safety information on hazardous chemical substances and mixtures. https://unece.org/about-ghs 81 HID https://pubchem.ncbi.nlm.nih.gov/classification/#hid=83 83

EPA CPDat Classification Classification from the U.S. Environmental Protection Agency's CPDat (Chemical and Products Database). This database contains information mapping more than 49,000 chemicals to a set of terms categorizing their usage or function in 16,000 consumer products (e.g. shampoo, soap) types based on what chemicals they contain. https://www.epa.gov/chemical-research/chemical-and-products-database-cpdat 84 HID https://pubchem.ncbi.nlm.nih.gov/classification/#hid=99 99

NORMAN Suspect List Exchange Classification A classification from the NORMAN Suspect List Exchange, which serve as a central access point to find lists of chemicals with environmental concerns. https://www.norman-network.com/nds/SLE/ 85 HID https://pubchem.ncbi.nlm.nih.gov/classification/#hid=101 101

EPA DSSTox Classification Classification from the U.S. Environmental Protection Agency's Distributed Structure-Searchable Toxicity (DSSTox) database. DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. A distinguishing feature of this effort is the accurate mapping of bioassay and physicochemical property data associated with chemical substances to their corresponding chemical structures. https://www.epa.gov/chemical-research/distributed-structure-searchable-toxicity-dsstox-database 86 HID https://pubchem.ncbi.nlm.nih.gov/classification/#hid=105 105

Consumer Product Information Database Classification Classification of the consumer products containing this compound, from the Consumer Product Information Database. https://www.whatsinproducts.com/ 87 HID https://pubchem.ncbi.nlm.nih.gov/classification/#hid=110 110

EPA TSCA and CDR Classification EPA Chemicals under the Toxic Substances Control Act (TSCA) collection contains information on chemicals and their regulation under TSCA. The chemical classification tree is created based on the TSCA substance regulatory flag, UVCB, and commercial activity status. https://www.epa.gov/tsca-inventory 90 HID https://pubchem.ncbi.nlm.nih.gov/classification/#hid=132 132

LOTUS Tree Biological and chemical tree provided by the naturaL prOducTs occUrrence databaSe (LOTUS) https://lotus.naturalproducts.net/ 89 HID https://pubchem.ncbi.nlm.nih.gov/classification/#hid=115 115

1 CAS Common Chemistry 127-41-3 α-Ionone CAS Common Chemistry is an open community resource for accessing chemical information. Nearly 500,000 chemical substances from CAS REGISTRY cover areas of community interest, including common and frequently regulated chemicals, and those relevant to high school and undergraduate chemistry classes. This chemical information, curated by our expert scientists, is provided in alignment with our mission as a division of the American Chemical Society. https://commonchemistry.cas.org/detail?cas_rn=127-41-3 The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated. https://creativecommons.org/licenses/by-nc/4.0/ 12847377 4 ChemIDplus 0000127413 alpha-Ionone ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system. https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0000127413 https://www.nlm.nih.gov/copyright.html true 766786 5 ChemIDplus 0006901979 alpha-Ionone ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system. https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0006901979 https://www.nlm.nih.gov/copyright.html true 819063 6 ChemIDplus 0014398368 (S-(E))-4-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-3-buten-2-one ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system. https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0014398368 https://www.nlm.nih.gov/copyright.html true 839675 7 ChemIDplus 0031798126 (-)-4-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-3-buten-2-one ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system. https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0031798126 https://www.nlm.nih.gov/copyright.html true 883116 11 DTP/NCI NSC 34560 IONONE, ALPHA The NCI Development Therapeutics Program (DTP) provides services and resources to the academic and private-sector research communities worldwide to facilitate the discovery and development of new cancer therapeutic agents. https://dtp.cancer.gov/dtpstandard/servlet/dwindex?searchtype=NSC&outputformat=html&searchlist=34560 Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source. https://www.cancer.gov/policies/copyright-reuse 6853381 13 EPA Chemical Data Reporting (CDR) 020a0670158761b480a0ac96ec030cf8 3-Buten-2-one, 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-, (3E)- The non-confidential content of the EPA Chemical Data Reporting. https://www.epa.gov/chemical-data-reporting The U.S. Government retains a nonexclusive, royalty-free license to publish or reproduce these documents, or allow others to do so, for U.S. Government purposes. These documents may be freely distributed and used for non-commercial, scientific and educational purposes. https://www.epa.gov/web-policies-and-procedures/epa-disclaimers#copyright 38381446 14 EPA Chemicals under the TSCA c5b430ab5b4bb86e65e175598fe56dd6 3-Buten-2-one, 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-, (3E)- EPA Chemicals under the Toxic Substances Control Act (TSCA) collection contains information on chemicals and their regulations under TSCA. https://www.epa.gov/chemicals-under-tsca https://www.epa.gov/privacy/privacy-act-laws-policies-and-resources 38390067 15 EPA DSSTox DTXSID0035160 alpha-Ionone DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. https://comptox.epa.gov/dashboard/DTXSID0035160 https://www.epa.gov/privacy/privacy-act-laws-policies-and-resources 1156605 18 European Chemicals Agency (ECHA) 204-841-6 4-(2,6,6-trimethylcyclohex-2-ene-1-yl)-but-3-ene-2-one The European Chemicals Agency (ECHA) is an agency of the European Union which is the driving force among regulatory authorities in implementing the EU's groundbreaking chemicals legislation for the benefit of human health and the environment as well as for innovation and competitiveness. https://echa.europa.eu/substance-information/-/substanceinfo/100.004.402 Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page. https://echa.europa.eu/web/guest/legal-notice 1978564 19 European Chemicals Agency (ECHA) 250-812-6 (-)-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one The European Chemicals Agency (ECHA) is an agency of the European Union which is the driving force among regulatory authorities in implementing the EU's groundbreaking chemicals legislation for the benefit of human health and the environment as well as for innovation and competitiveness. https://echa.europa.eu/substance-information/-/substanceinfo/100.046.178 Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page. https://echa.europa.eu/web/guest/legal-notice 2023182 20 European Chemicals Agency (ECHA) 230-010-2 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one The European Chemicals Agency (ECHA) is an agency of the European Union which is the driving force among regulatory authorities in implementing the EU's groundbreaking chemicals legislation for the benefit of human health and the environment as well as for innovation and competitiveness. https://echa.europa.eu/substance-information/-/substanceinfo/100.027.282 Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page. https://echa.europa.eu/web/guest/legal-notice 2078831 22 FDA Global Substance Registration System (GSRS) I9V075M61R .ALPHA.-IONONE The FDA Global Substance Registration System (GSRS) enables the efficient and accurate exchange of information on what substances are in regulated products. Instead of relying on names, which vary across regulatory domains, countries, and regions, the GSRS knowledge base makes it possible for substances to be defined by standardized, scientific descriptions. https://gsrs.ncats.nih.gov/ginas/app/beta/substances/I9V075M61R Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required. https://www.fda.gov/about-fda/about-website/website-policies#linking 5798745 26 Hazardous Substances Data Bank (HSDB) 8268 alpha-Ionone The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. https://pubchem.ncbi.nlm.nih.gov/source/hsdb/8268 https://www.nlm.nih.gov/web_policies.html true 5777 30 International Fragrance Association (IFRA) 6e3039e800a36668b37845c4d1eb5445 alpha-Ionone The IFRA Fragrance Ingredient Glossary (FIG), provides a harmonized list of positive olfactory descriptors of fragrance ingredients. https://ifrafragrance.org/priorities/ingredients/ifra-transparency-list (c) The International Fragrance Association, 2007-2021. All rights reserved. https://ifrafragrance.org/links/copyright 37135094 44 New Zealand Environmental Protection Authority (EPA) 713f34765a872b458716cdd626c52e47 alpha-Ionone The New Zealand Environmental Protection Authority is a government agency for regulating activities that affect Aotearoa New Zealand's environment. https://www.epa.govt.nz/industry-areas/hazardous-substances/guidance-for-importers-and-manufacturers/hazardous-substances-databases/ This work is licensed under the Creative Commons Attribution-ShareAlike 4.0 International licence. https://www.epa.govt.nz/about-this-site/general-copyright-statement/ 37142220 2 ChEBI CHEBI:OBO:5282108 Alpha-ionone Chemical Entities of Biological Interest (ChEBI) is a database and ontology of molecular entities focused on 'small' chemical compounds, that is part of the Open Biomedical Ontologies effort. The term "molecular entity" refers to any constitutionally or isotopically distinct atom, molecule, ion, ion pair, radical, radical ion, complex, conformer, etc., identifiable as a separately distinguishable entity. https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:32319 2491026 38 LOTUS - the natural products occurrence database Q27114869 alpha-Ionone LOTUS is one of the biggest and best annotated resources for natural products occurrences available free of charge and without any restriction. https://www.wikidata.org/wiki/Q27114869 The code for LOTUS is released under the GNU General Public License v3.0. https://lotus.nprod.net/ 19828262 72 Toxin and Toxin Target Database (T3DB) Compound::T3D4940 alpha-Ionone The Toxin and Toxin Target Database (T3DB), or, soon to be referred as, the Toxic Exposome Database, is a unique bioinformatics resource that combines detailed toxin data with comprehensive toxin target information. http://www.t3db.ca/toxins/T3D4940 T3DB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (T3DB) and the original publication. http://www.t3db.ca/downloads 20444028 3 ChEMBL Compound::CHEMBL472877 ChEMBL or ChEMBLdb is a manually curated chemical database of bioactive molecules with drug-like properties. It is maintained by the European Bioinformatics Institute (EBI), of the European Molecular Biology Laboratory (EMBL), based at the Wellcome Trust Genome Campus, Hinxton, UK. https://www.ebi.ac.uk/chembl/compound_report_card/CHEMBL472877/ Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/). http://www.ebi.ac.uk/Information/termsofuse.html 31678328 8 ChemIDplus r_134974059 The toxicity data was from the legacy RTECS data set in ChemIDplus. https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0000127413 https://www.nlm.nih.gov/copyright.html true 19465480 9 Comparative Toxicogenomics Database (CTD) C011879::Compound alpha-ionone CTD is a robust, publicly available database that aims to advance understanding about how environmental exposures affect human health. https://ctdbase.org/detail.go?type=chem&acc=C011879 It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University. http://ctdbase.org/about/legal.jsp 9013741 10 Consumer Product Information Database (CPID) 504 Alpha-Ionone The Consumer Product Information Database (CPID) contains health effects information for products used in the home and in some commercial/institutional settings that contain chemicals. The CPID is unique in that it will, for the first time, link brand names to health effects and allow consumers to select brands based on their individual sensitivity to specific chemical ingredients. https://www.whatsinproducts.com/chemicals/view/1/6296/000127-41-3 Copyright (c) 2023 DeLima Associates. All rights reserved. Unless otherwise indicated, all materials from CPID are copyrighted by DeLima Associates. No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission. https://www.whatsinproducts.com/contents/view/1/6 5124518 12 EPA Chemical and Products Database (CPDat) 1273_DTXSID0035160 The US EPA Chemical and Products Database (CPDat) is a database containing information mapping more than 49,000 chemicals to a set of terms categorizing their usage or function in 16,000 consumer products (e.g. shampoo, soap) types based on what chemicals they contain. https://comptox.epa.gov/dashboard/DTXSID0035160#exposure https://www.epa.gov/privacy/privacy-act-laws-policies-and-resources 13731780 35 Joint FAO/WHO Expert Committee on Food Additives (JECFA) f_667 alpha-Ionone The flavoring agent databse provides the most recent specifications for flavorings evaluated by JECFA. https://www.fao.org/food/food-safety-quality/scientific-advice/jecfa/jecfa-flav/details/en/c/667/ Permission from WHO is not required for the use of WHO materials issued under the Creative Commons Attribution-NonCommercial-ShareAlike 3.0 Intergovernmental Organization (CC BY-NC-SA 3.0 IGO) licence. https://www.who.int/about/policies/publishing/copyright 9156814 16 EU Food Improvement Agents 07.007 alpha-Ionone Commission Implementing Regulation (EU) No 872/2012 of 1 October 2012 adopting the list of flavouring substances provided for by Regulation (EC) No 2232/96 of the European Parliament and of the Council, introducing it in Annex I to Regulation (EC) No 1334/2008 of the European Parliament and of the Council and repealing Commission Regulation (EC) No 1565/2000 and Commission Decision 1999/217/EC Text with EEA relevance https://eur-lex.europa.eu/legal-content/EN/TXT/?uri=CELEX:32012R0872 5177923 34 Joint FAO/WHO Expert Committee on Food Additives (JECFA) wf_610 alpha-CYCLOCITRYLIDENEACETONE Evaluations of the Joint FAO/WHO Expert Committee on Food Additives (JECFA) database contains the summaries of all the evaluations of flavors, food additives, contaminants, toxicants, and veterinary drugs. https://apps.who.int/food-additives-contaminants-jecfa-database/Home/Chemical/610 Permission from WHO is not required for the use of WHO materials issued under the Creative Commons Attribution-NonCommercial-ShareAlike 3.0 Intergovernmental Organization (CC BY-NC-SA 3.0 IGO) licence. https://www.who.int/about/policies/publishing/copyright 9153010 36 Joint FAO/WHO Expert Committee on Food Additives (JECFA) wf_901 alpha-IONONE Evaluations of the Joint FAO/WHO Expert Committee on Food Additives (JECFA) database contains the summaries of all the evaluations of flavors, food additives, contaminants, toxicants, and veterinary drugs. https://apps.who.int/food-additives-contaminants-jecfa-database/Home/Chemical/901 Permission from WHO is not required for the use of WHO materials issued under the Creative Commons Attribution-NonCommercial-ShareAlike 3.0 Intergovernmental Organization (CC BY-NC-SA 3.0 IGO) licence. https://www.who.int/about/policies/publishing/copyright 15262588 17 European Chemicals Agency (ECHA) 78026 4-(2,6,6-trimethylcyclohex-2-ene-1-yl)-but-3-ene-2-one The information provided here is aggregated from the "Notified classification and labelling" from ECHA's C&L Inventory. Read more: https://echa.europa.eu/information-on-chemicals/cl-inventory-database https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/78026 Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page. https://echa.europa.eu/web/guest/legal-notice 1874119 25 Hazardous Chemical Information System (HCIS), Safe Work Australia 5903 127-41-3 The Hazardous Chemical Information System (HCIS) at the Safe Work Australia is a database of chemical classifications and workplace exposure standards. It allows users to find information on chemicals that have been classified in accordance with the GHS or which have an Australian Workplace Exposure Standard. http://hcis.safeworkaustralia.gov.au/HazardousChemical/Details?chemicalID=5903 12656054 21 FDA Center for Food Safety and Applied Nutrition (CFSAN) e_1835 ALPHA-IONONE The Substances Added to Food (formerly EAFUS) inventory includes information on food additives, color additives, Generally Recognized As Safe (GRAS) and prior-sanctioned substances. https://www.cfsanappsexternal.fda.gov/scripts/fdcc/index.cfm?set=FoodSubstances https://www.cfsanappsexternal.fda.gov/scripts/fdcc/index.cfm?set=FoodSubstances&id=IONONEalpha Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required. https://www.fda.gov/about-fda/about-website/website-policies#linking 6476762 23 Flavor and Extract Manufacturers Association (FEMA) 2594 ALPHA-IONONE FEMA, The Flavor and Extract Manufacturers Association of the United States, is comprised of flavor manufacturers, flavor users, flavor ingredient suppliers, and others with an interest in the U.S. flavor industry. Read more: https://www.femaflavor.org/ https://www.femaflavor.org/flavor-library/alpha-ionone 6879190 24 FooDB Compound::FDB014484 alpha-Ionone FooDB is the world's largest and most comprehensive resource on food constituents, chemistry and biology. It provides information on both macronutrients and micronutrients, including many of the constituents that give foods their flavor, color, taste, texture and aroma. https://foodb.ca/compounds/FDB014484 FooDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (FooDB) and the original publication. https://foodb.ca/about 38491984 27 Human Metabolome Database (HMDB) HMDB0059883 alpha-Ionone The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. http://www.hmdb.ca/metabolites/HMDB0059883 HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. http://www.hmdb.ca/citing 2182262 28 Human Metabolome Database (HMDB) HMDB0059883_nmr_one_3500 HMDB0059883_nmr_one_3500 The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. https://hmdb.ca/metabolites/HMDB0059883#spectra HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. http://www.hmdb.ca/citing 15341063 68 SpectraBase 7zHL5kFbzPw alpha-Ionone Wiley Science Solutions (https://sciencesolutions.wiley.com) is a leading publisher of spectral databases and KnowItAll spectroscopy software. SpectraBase provides fast text access to hundreds of thousands of NMR, IR, Raman, UV-Vis, and mass spectra. https://spectrabase.com/spectrum/7zHL5kFbzPw 13586321 29 Human Metabolome Database (HMDB) HMDB0059883_nmr_one_3642 HMDB0059883_nmr_one_3642 The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. https://hmdb.ca/metabolites/HMDB0059883#spectra HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. http://www.hmdb.ca/citing 15341064 56 SpectraBase GKmjGMuUUZs alpha-IONONE Wiley Science Solutions (https://sciencesolutions.wiley.com) is a leading publisher of spectral databases and KnowItAll spectroscopy software. SpectraBase provides fast text access to hundreds of thousands of NMR, IR, Raman, UV-Vis, and mass spectra. https://spectrabase.com/spectrum/GKmjGMuUUZs 4621470 62 SpectraBase 7iFEQnZ32rh 3-BUTEN-2-ONE, 4-(2,6,6-TRIMETHYL-2-CYCLOHEXEN-1-YL)- Wiley Science Solutions (https://sciencesolutions.wiley.com) is a leading publisher of spectral databases and KnowItAll spectroscopy software. SpectraBase provides fast text access to hundreds of thousands of NMR, IR, Raman, UV-Vis, and mass spectra. https://spectrabase.com/spectrum/7iFEQnZ32rh 9781500 31 Japan Chemical Substance Dictionary (Nikkaji) J183.660I The Japan Chemical Substance Dictionary (Nikkaji) has a search system that helps obtain knowledge from dissimilar fields and discover concepts that cross boundaries of specializations. http://jglobal.jst.go.jp/en/redirect?Nikkaji_No=J183.660I 21364857 32 Japan Chemical Substance Dictionary (Nikkaji) J2.016H The Japan Chemical Substance Dictionary (Nikkaji) has a search system that helps obtain knowledge from dissimilar fields and discover concepts that cross boundaries of specializations. http://jglobal.jst.go.jp/en/redirect?Nikkaji_No=J2.016H 21398163 33 Japan Chemical Substance Dictionary (Nikkaji) J278.189A The Japan Chemical Substance Dictionary (Nikkaji) has a search system that helps obtain knowledge from dissimilar fields and discover concepts that cross boundaries of specializations. http://jglobal.jst.go.jp/en/redirect?Nikkaji_No=J278.189A 21717760 37 KEGG C12286 KEGG is an encyclopedia of genes and genomes. Assigning functional meanings to genes and genomes both at the molecular and higher levels is the primary objective of the KEGG database project. https://www.kegg.jp/entry/C12286 Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license https://www.kegg.jp/kegg/legal.html 31098968 43 Natural Product Activity and Species Source (NPASS) NPC14002 Alpha-Ionone The Natural Product Activity and Species Source Database (NPASS) is developed to provide a freely accessible database integrating detailed information of species sources and biological activities of natural products. https://bidd.group/NPASS/compound.php?compoundID=NPC14002 20337115 73 West Coast Metabolomics Center-UC Davis 1.08_193.16_1.09_175.15 alpha-Lonone or beta-Damascone The West Coast Metabolomics Center (WCMC) at the University of California Davis develops and applies liquid/gas chromatography and mass spectrometry assays and computational methods for measuring small molecules in biospecimens. 19796213 39 MassBank of North America (MoNA) JP002591 ALPHA-IONONE MassBank of North America (MoNA) is a metadata-centric, auto-curating repository designed for efficient storage and querying of mass spectral records. There are total 6 MS data records(6 experimental records) for this compound, click the link above to see all spectral information at MoNA website. https://mona.fiehnlab.ucdavis.edu/spectra/browse?query=exists(compound.metaData.name:%27InChIKey%27%20and%20compound.metaData.value:%27UZFLPKAIBPNNCA-GUOLPTJISA-N%27) The content of the MoNA database is licensed under CC BY 4.0. https://mona.fiehnlab.ucdavis.edu/documentation/license 3418524 40 MassBank of North America (MoNA) JP006612 ALPHA-IONONE MassBank of North America (MoNA) is a metadata-centric, auto-curating repository designed for efficient storage and querying of mass spectral records. There are total 6 MS data records(6 experimental records) for this compound, click the link above to see all spectral information at MoNA website. https://mona.fiehnlab.ucdavis.edu/spectra/browse?query=exists(compound.metaData.name:%27InChIKey%27%20and%20compound.metaData.value:%27UZFLPKAIBPNNCA-GUOLPTJISA-N%27) The content of the MoNA database is licensed under CC BY 4.0. https://mona.fiehnlab.ucdavis.edu/documentation/license 3422255 41 MassBank of North America (MoNA) JP007557 ALPHA-IONONE MassBank of North America (MoNA) is a metadata-centric, auto-curating repository designed for efficient storage and querying of mass spectral records. There are total 6 MS data records(6 experimental records) for this compound, click the link above to see all spectral information at MoNA website. https://mona.fiehnlab.ucdavis.edu/spectra/browse?query=exists(compound.metaData.name:%27InChIKey%27%20and%20compound.metaData.value:%27UZFLPKAIBPNNCA-GUOLPTJISA-N%27) The content of the MoNA database is licensed under CC BY 4.0. https://mona.fiehnlab.ucdavis.edu/documentation/license 3423128 45 NIST Mass Spectrometry Data Center GC-MS #1 for UZFLPKAIBPNNCA-BQYQJAHWSA-N Ionone The NIST Mass Spectrometry Data Center, a Group in the Biomolecular Measurement Division (BMD), develops evaluated mass spectral libraries and provides related software tools. These products are intended to assist compound identification by providing reference mass spectra for GC/MS (by electron ionization) and LC-MS/MS (by tandem mass spectrometry) as well as gas phase retention indices for GC. http://www.nist.gov/srd/nist1a.cfm Data covered by the Standard Reference Data Act of 1968 as amended. https://www.nist.gov/srd/public-law 107877 46 NIST Mass Spectrometry Data Center GC-MS #2 for UZFLPKAIBPNNCA-BQYQJAHWSA-N .alpha.-Ionone The NIST Mass Spectrometry Data Center, a Group in the Biomolecular Measurement Division (BMD), develops evaluated mass spectral libraries and provides related software tools. These products are intended to assist compound identification by providing reference mass spectra for GC/MS (by electron ionization) and LC-MS/MS (by tandem mass spectrometry) as well as gas phase retention indices for GC. http://www.nist.gov/srd/nist1a.cfm Data covered by the Standard Reference Data Act of 1968 as amended. https://www.nist.gov/srd/public-law 108432 47 NIST Mass Spectrometry Data Center GC-MS #3 for UZFLPKAIBPNNCA-BQYQJAHWSA-N 3-Buten-2-one, 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)- The NIST Mass Spectrometry Data Center, a Group in the Biomolecular Measurement Division (BMD), develops evaluated mass spectral libraries and provides related software tools. These products are intended to assist compound identification by providing reference mass spectra for GC/MS (by electron ionization) and LC-MS/MS (by tandem mass spectrometry) as well as gas phase retention indices for GC. http://www.nist.gov/srd/nist1a.cfm Data covered by the Standard Reference Data Act of 1968 as amended. https://www.nist.gov/srd/public-law 108433 48 NIST Mass Spectrometry Data Center GC-MS #4 for UZFLPKAIBPNNCA-BQYQJAHWSA-N .alpha.-Ionone The NIST Mass Spectrometry Data Center, a Group in the Biomolecular Measurement Division (BMD), develops evaluated mass spectral libraries and provides related software tools. These products are intended to assist compound identification by providing reference mass spectra for GC/MS (by electron ionization) and LC-MS/MS (by tandem mass spectrometry) as well as gas phase retention indices for GC. http://www.nist.gov/srd/nist1a.cfm Data covered by the Standard Reference Data Act of 1968 as amended. https://www.nist.gov/srd/public-law 266819 49 NIST Mass Spectrometry Data Center GC-MS #5 for UZFLPKAIBPNNCA-BQYQJAHWSA-N .alpha.-Ionone The NIST Mass Spectrometry Data Center, a Group in the Biomolecular Measurement Division (BMD), develops evaluated mass spectral libraries and provides related software tools. These products are intended to assist compound identification by providing reference mass spectra for GC/MS (by electron ionization) and LC-MS/MS (by tandem mass spectrometry) as well as gas phase retention indices for GC. http://www.nist.gov/srd/nist1a.cfm Data covered by the Standard Reference Data Act of 1968 as amended. https://www.nist.gov/srd/public-law 266820 50 NIST Mass Spectrometry Data Center GC-MS #6 for UZFLPKAIBPNNCA-BQYQJAHWSA-N .alpha.-Ionone The NIST Mass Spectrometry Data Center, a Group in the Biomolecular Measurement Division (BMD), develops evaluated mass spectral libraries and provides related software tools. These products are intended to assist compound identification by providing reference mass spectra for GC/MS (by electron ionization) and LC-MS/MS (by tandem mass spectrometry) as well as gas phase retention indices for GC. http://www.nist.gov/srd/nist1a.cfm Data covered by the Standard Reference Data Act of 1968 as amended. https://www.nist.gov/srd/public-law 266847 51 NIST Mass Spectrometry Data Center GC-MS #7 for UZFLPKAIBPNNCA-BQYQJAHWSA-N .alpha.-Ionone The NIST Mass Spectrometry Data Center, a Group in the Biomolecular Measurement Division (BMD), develops evaluated mass spectral libraries and provides related software tools. These products are intended to assist compound identification by providing reference mass spectra for GC/MS (by electron ionization) and LC-MS/MS (by tandem mass spectrometry) as well as gas phase retention indices for GC. http://www.nist.gov/srd/nist1a.cfm Data covered by the Standard Reference Data Act of 1968 as amended. https://www.nist.gov/srd/public-law 266848 52 NIST Mass Spectrometry Data Center GC-MS #8 for UZFLPKAIBPNNCA-BQYQJAHWSA-N 3-Buten-2-one, 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)- The NIST Mass Spectrometry Data Center, a Group in the Biomolecular Measurement Division (BMD), develops evaluated mass spectral libraries and provides related software tools. These products are intended to assist compound identification by providing reference mass spectra for GC/MS (by electron ionization) and LC-MS/MS (by tandem mass spectrometry) as well as gas phase retention indices for GC. http://www.nist.gov/srd/nist1a.cfm Data covered by the Standard Reference Data Act of 1968 as amended. https://www.nist.gov/srd/public-law 266850 60 SpectraBase KnudVAfFKn8 4-(2,6,6-TRIMETHYLCYCLOHEX-2-ENYL)BUT-3-EN-2-ONE Wiley Science Solutions (https://sciencesolutions.wiley.com) is a leading publisher of spectral databases and KnowItAll spectroscopy software. SpectraBase provides fast text access to hundreds of thousands of NMR, IR, Raman, UV-Vis, and mass spectra. https://spectrabase.com/spectrum/KnudVAfFKn8 9781497 61 SpectraBase GJGB9xsccAG alpha-IONONE Wiley Science Solutions (https://sciencesolutions.wiley.com) is a leading publisher of spectral databases and KnowItAll spectroscopy software. SpectraBase provides fast text access to hundreds of thousands of NMR, IR, Raman, UV-Vis, and mass spectra. https://spectrabase.com/spectrum/GJGB9xsccAG 9781498 42 Metabolomics Workbench 54536 alpha-ionone The Metabolomics Workbench serves as a national and international repository for metabolomics data and metadata and provides analysis tools and access to metabolite standards, protocols, tutorials, training, and more. https://www.metabolomicsworkbench.org/data/StructureData.php?RegNo=54536 20212954 53 NIST Mass Spectrometry Data Center RI for UZFLPKAIBPNNCA-BQYQJAHWSA-N .alpha.-Ionone , "Ionone" http://www.nist.gov/srd/nist1a.cfm Data covered by the Standard Reference Data Act of 1968 as amended. https://www.nist.gov/srd/public-law 292950 54 NLM RxNorm Terminology 1859172 alpha ionone RxNorm provides normalized names for clinical drugs and links its names to many of the drug vocabularies commonly used in pharmacy management and drug interaction software. https://rxnav.nlm.nih.gov/id/rxnorm/1859172 The RxNorm Terminology is created by the National Library of Medicine (NLM) and is in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from NLM. Credit to the U.S. National Library of Medicine as the source is appreciated but not required. The full RxNorm dataset requires a free license. https://www.nlm.nih.gov/research/umls/rxnorm/docs/termsofservice.html 31179229 55 SpectraBase 6eaTprYXZjt alpha-IONONE Wiley Science Solutions (https://sciencesolutions.wiley.com) is a leading publisher of spectral databases and KnowItAll spectroscopy software. SpectraBase provides fast text access to hundreds of thousands of NMR, IR, Raman, UV-Vis, and mass spectra. https://spectrabase.com/spectrum/6eaTprYXZjt 4621469 57 SpectraBase 2LHqg51Vkrl alpha-Jonon Wiley Science Solutions (https://sciencesolutions.wiley.com) is a leading publisher of spectral databases and KnowItAll spectroscopy software. SpectraBase provides fast text access to hundreds of thousands of NMR, IR, Raman, UV-Vis, and mass spectra. https://spectrabase.com/spectrum/2LHqg51Vkrl 9781494 58 SpectraBase emWYHfM2JY 3-Buten-2-one, 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-, (E)- Wiley Science Solutions (https://sciencesolutions.wiley.com) is a leading publisher of spectral databases and KnowItAll spectroscopy software. SpectraBase provides fast text access to hundreds of thousands of NMR, IR, Raman, UV-Vis, and mass spectra. https://spectrabase.com/spectrum/emWYHfM2JY 9781495 59 SpectraBase LYp6qOV659t 3-Buten-2-one, 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-, (E)- Wiley Science Solutions (https://sciencesolutions.wiley.com) is a leading publisher of spectral databases and KnowItAll spectroscopy software. SpectraBase provides fast text access to hundreds of thousands of NMR, IR, Raman, UV-Vis, and mass spectra. https://spectrabase.com/spectrum/LYp6qOV659t 9781496 63 SpectraBase 3NYFpDjUb38 (3E)-4-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-3-buten-2-one Wiley Science Solutions (https://sciencesolutions.wiley.com) is a leading publisher of spectral databases and KnowItAll spectroscopy software. SpectraBase provides fast text access to hundreds of thousands of NMR, IR, Raman, UV-Vis, and mass spectra. https://spectrabase.com/spectrum/3NYFpDjUb38 9781526 67 SpectraBase 5skKlG6C3jA alpha-Ionone Wiley Science Solutions (https://sciencesolutions.wiley.com) is a leading publisher of spectral databases and KnowItAll spectroscopy software. SpectraBase provides fast text access to hundreds of thousands of NMR, IR, Raman, UV-Vis, and mass spectra. https://spectrabase.com/spectrum/5skKlG6C3jA 9781560 64 SpectraBase LL3ynnehcLF (3E)-4-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-3-buten-2-one Wiley Science Solutions (https://sciencesolutions.wiley.com) is a leading publisher of spectral databases and KnowItAll spectroscopy software. SpectraBase provides fast text access to hundreds of thousands of NMR, IR, Raman, UV-Vis, and mass spectra. https://spectrabase.com/spectrum/LL3ynnehcLF 9781527 65 SpectraBase GvqjEAdBObj alpha-Ionone Wiley Science Solutions (https://sciencesolutions.wiley.com) is a leading publisher of spectral databases and KnowItAll spectroscopy software. SpectraBase provides fast text access to hundreds of thousands of NMR, IR, Raman, UV-Vis, and mass spectra. https://spectrabase.com/spectrum/GvqjEAdBObj 9781556 66 SpectraBase hpSRzykhzR alpha-Ionone Wiley Science Solutions (https://sciencesolutions.wiley.com) is a leading publisher of spectral databases and KnowItAll spectroscopy software. SpectraBase provides fast text access to hundreds of thousands of NMR, IR, Raman, UV-Vis, and mass spectra. https://spectrabase.com/spectrum/hpSRzykhzR 9781559 69 SpectraBase CaP6WsJy2Nq alpha-Ionone Wiley Science Solutions (https://sciencesolutions.wiley.com) is a leading publisher of spectral databases and KnowItAll spectroscopy software. SpectraBase provides fast text access to hundreds of thousands of NMR, IR, Raman, UV-Vis, and mass spectra. https://spectrabase.com/spectrum/CaP6WsJy2Nq 13586322 70 Springer Nature 14044385-205728090 Springer Nature is the world's largest academic book publisher, publisher of the world's most influential journals, and a pioneer in the field of open research. SpringerLink provides electronic access to its book and journal content. https://pubchem.ncbi.nlm.nih.gov/substance/?source=15745&sourceid=14044385-205728090 3847105 71 Thieme Chemistry 14044385-205728090 Thieme Chemistry is part of the privately owned Thieme Group and publishes highly evaluated information about synthetic and general chemistry for professional chemists and advanced students since 1909. Our portfolio includes the journals SYNFACTS, SYNLETT, SYNTHESIS and SynOpen, the synthetic methodology reference work Science of Synthesis, the German chemical encyclopedia ROEMPP, and monographs in electronic and printed format. The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license (https://creativecommons.org/licenses/by-nc-nd/4.0/), unless otherwise stated. https://pubchem.ncbi.nlm.nih.gov/substance/?source=22163&sourceid=14044385-205728090 The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated. https://creativecommons.org/licenses/by-nc-nd/4.0/ 5297491 74 Wikidata Q27114869 alpha-ionone Link to the compound information in Wikidata. https://www.wikidata.org/wiki/Q27114869 CCZero https://creativecommons.org/publicdomain/zero/1.0/ 16338006 75 PubChem PubChem Data deposited in or computed by PubChem https://pubchem.ncbi.nlm.nih.gov 76 Medical Subject Headings (MeSH) 67011879 alpha-ionone MeSH (Medical Subject Headings) is the U.S. National Library of Medicine's controlled vocabulary thesaurus used for indexing articles for PubMed. https://www.ncbi.nlm.nih.gov/mesh/67011879 Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S. https://www.nlm.nih.gov/copyright.html 77 Medical Subject Headings (MeSH) DescTree MeSH Tree MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed. http://www.nlm.nih.gov/mesh/meshhome.html Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S. https://www.nlm.nih.gov/copyright.html 78 ChEBI OBO ChEBI Ontology The ChEBI Ontology is a structured classification of the entities contained within ChEBI. http://www.ebi.ac.uk/chebi/userManualForward.do#ChEBI%20Ontology 79 KEGG br08003 Phytochemical compounds KEGG is an encyclopedia of genes and genomes. Assigning functional meanings to genes and genomes both at the molecular and higher levels is the primary objective of the KEGG database project. http://www.genome.jp/kegg-bin/get_htext?br08003.keg Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license https://www.kegg.jp/kegg/legal.html 81 GHS Classification (UNECE) UN_GHS_tree GHS Classification Tree The United Nations' Globally Harmonized System of Classification and Labeling of Chemicals (GHS) provides a harmonized basis for globally uniform physical, environmental, and health and safety information on hazardous chemical substances and mixtures. It sets up criteria for the classification of chemicals for physical-chemical, health, and environmental hazards of chemical substances and mixtures and sets up standardized hazard information to facilitate global trade of chemicals. Please note that obsolete codes are added in this classification for completeness purposes, as they are still in use. Any obsolete codes are annotated as such. http://www.unece.org/trans/danger/publi/ghs/ghs_welcome_e.html 82 ChemIDplus ChemIDplus_tree ChemIDplus Chemical Information Classification ChemIDplus is a TOXNET (TOXicology Data NETwork) databases that contain chemicals and drugs related information. It is a product of the National Library of Medicine (NLM). https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus https://www.nlm.nih.gov/copyright.html true 83 ChEMBL Target Tree ChEMBL Protein Target Tree The ChEMBL Protein Target Tree is a structured classification of the protein target entities contained with the ChEMBL resource release version 34 ChEMBL. https://www.ebi.ac.uk/chembl/g/#browse/targets Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/). http://www.ebi.ac.uk/Information/termsofuse.html 84 EPA Chemical and Products Database (CPDat) cpdat_tree EPA CPDat Classification CPDat (Chemical and Products Database) is a database containing information mapping more than 49,000 chemicals to a set of terms categorizing their usage or function in 16,000 consumer products. Ref: The Chemical and Products Database, a resource for exposure-relevant data on chemicals in consumer products, Scientific Data, volume 5, Article number: 180125 (2018), DOI:10.1038/sdata.2018.125 https://www.epa.gov/chemical-research/chemical-and-products-database-cpdat https://www.epa.gov/privacy/privacy-act-laws-policies-and-resources 85 NORMAN Suspect List Exchange norman_sle_tree NORMAN Suspect List Exchange Classification The NORMAN Suspect List Exchange (NORMAN-SLE) is a central access point for NORMAN members (and others) to find suspect lists relevant for their environmental monitoring questions.<br>Update: 2024-05-28 18:00:01 https://www.norman-network.com/nds/SLE/ Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0 https://creativecommons.org/licenses/by/4.0/ 86 EPA DSSTox dsstoxlist_tree CompTox Chemicals Dashboard Chemical Lists This classification lists the chemical categories from the EPA CompTox Chemicals Dashboard.<br>Update: 2024-04-30 09:21:02 https://comptox.epa.gov/dashboard/chemical-lists/ https://www.epa.gov/privacy/privacy-act-laws-policies-and-resources 87 Consumer Product Information Database (CPID) cpid_tree Consumer Products Category Classification The Consumer product category classification is based on the Consumer Product Information Database ©2001-2021 by DeLima Associates. https://www.whatsinproducts.com/ Copyright (c) 2024 DeLima Associates. All rights reserved. Unless otherwise indicated, all materials from CPID are copyrighted by DeLima Associates. No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission. https://www.whatsinproducts.com/contents/view/1/6 89 LOTUS - the natural products occurrence database biochem LOTUS Tree Biological and chemical tree provided by the LOTUS (naturaL products occurrence database) https://lotus.naturalproducts.net/ The code for LOTUS is released under the GNU General Public License v3.0. https://lotus.nprod.net/ 90 EPA Chemicals under the TSCA epa_tsca_tree EPA TSCA and CDR Classification EPA Chemicals under the Toxic Substances Control Act (TSCA) collection contains information on chemicals and their regulation under TSCA. The chemical classification tree is created based on the TSCA substance regulatory flag, UVCB, and commercial activity status.<br>Update: 2024-04-22 17:13:45 https://www.epa.gov/tsca-inventory https://www.epa.gov/privacy/privacy-act-laws-policies-and-resources 91 PATENTSCOPE (WIPO) SID 403385553 The PATENTSCOPE database from WIPO includes patent and chemical structure search (with a free account) that gives access to millions of patent documents. The World Intellectual Property Organisation (WIPO) is a specialized United Nations (UN) agency headquartered in Geneva (Switzerland). Our mission is to lead the development of a balanced and effective international Intellectual Property (IP) system that enables innovation and creativity for the benefit of all. We help governments, businesses and society realize the benefits of Intellectual Property and are notably a world reference source for IP information. https://pubchem.ncbi.nlm.nih.gov/substance/403385553