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4-Hydroxy-4-methyl-7-decenoic acid gamma-lactone

PubChem CID
6436439
Structure
4-Hydroxy-4-methyl-7-decenoic acid gamma-lactone_small.png
4-Hydroxy-4-methyl-7-decenoic acid gamma-lactone_3D_Structure.png
Molecular Formula
Synonyms
  • 14252-84-7
  • (E)-3-Hexenyldihydro-5-methylfuran-2(3H)-one
  • 4-Hydroxy-4-methyl-7-decenoic acid gamma-lactone
  • Cis-jasmonolactone
  • 4-Methyl-cis-decene gamma-lactone
Molecular Weight
182.26 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2006-04-28
  • Modify:
    2025-01-18
Description
4-Hydroxy-4-methyl-7-decenoic acid gamma-lactone is a gamma-lactone.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
4-Hydroxy-4-methyl-7-decenoic acid gamma-lactone.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

5-[(E)-hex-3-enyl]-5-methyloxolan-2-one
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C11H18O2/c1-3-4-5-6-8-11(2)9-7-10(12)13-11/h4-5H,3,6-9H2,1-2H3/b5-4+
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

NIKDJTTZUYNCMM-SNAWJCMRSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CC/C=C/CCC1(CCC(=O)O1)C
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C11H18O2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

70851-61-5
14252-84-7

2.3.2 European Community (EC) Number

2.3.3 ChEBI ID

2.3.4 DSSTox Substance ID

2.3.5 FEMA Number

2.3.6 HMDB ID

2.3.7 JECFA Number

1159

2.3.8 Metabolomics Workbench ID

2.3.9 Nikkaji Number

2.4 Synonyms

2.4.1 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
182.26 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
2.6
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
182.130679813 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
182.130679813 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
26.3 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
13
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
208
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

Colourless liquid; fresh herbaceous note

3.2.2 Boiling Point

150.00 °C. @ 6.00 mm Hg
The Good Scents Company Information System

3.2.3 Solubility

Insoluble in water; soluble in oil
soluble (in ethanol)

3.2.4 Density

0.960-0.967

3.2.5 Refractive Index

1.463-1.468

3.2.6 Kovats Retention Index

Standard polar
1893

3.3 Chemical Classes

3.3.1 Food Additives

FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food

3.3.2 Fragrances

Fragrance Ingredient (5-(cis-3-Hexenyl)dihydro-5-methyl-2(3H)furanone) -> IFRA transparency List

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 GC-MS

1 of 2
Source of Spectrum
Adams' Essential Oil Components (GC-MS), Version 4
Copyright
Database Compilation Copyright © 2023-2024 John Wiley and Sons, Inc. Copyright © 2023-2024 John Wiley and Sons, Inc., Portions Copyright Wiley-VCH GmbH, Adams Library under license from Diablo Analytical. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Source of Spectrum
Prof. L. Mondello (Chromaleont s.r.l./Univ. Messina, Italy)
Copyright
Database Compilation Copyright © 2023-2024 John Wiley and Sons, Inc. Copyright © 2023-2024 John Wiley and Sons, Inc., Portions Copyright Wiley-VCH GmbH, Adams Library under license from Diablo Analytical. All Rights Reserved.
Thumbnail
Thumbnail

6 Chemical Vendors

7 Food Additives and Ingredients

7.1 Food Additive Classes

Flavoring Agents
JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT;

7.2 FEMA Flavor Profile

Savory

7.3 FDA Substances Added to Food

Used for (Technical Effect)
FLAVORING AGENT OR ADJUVANT
FEMA Number
3937
GRAS Number
19
JECFA Flavor Number
1159

7.4 Evaluations of the Joint FAO / WHO Expert Committee on Food Additives - JECFA

Chemical Name
4-HYDROXY-4-METHYL-7-cis-DECENOIC ACID gamma LACTONE
Evaluation Year
2008
ADI
No safety concern at current levels of intake when used as a flavouring agent

8 Pharmacology and Biochemistry

8.1 Human Metabolite Information

8.1.1 Cellular Locations

Membrane

9 Use and Manufacturing

9.1 Uses

9.1.1 Use Classification

Food additives -> Flavoring Agents
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT; -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index

9.2 General Manufacturing Information

EPA TSCA Commercial Activity Status
2(3H)-Furanone, 5-(3Z)-3-hexen-1-yldihydro-5-methyl-: ACTIVE

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

Note
This chemical does not meet GHS hazard criteria for 99.2% (125 of 126) of all reports. Pictograms displayed are for 0.8% (1 of 126) of reports that indicate hazard statements.
GHS Hazard Statements

Not Classified

Reported as not meeting GHS hazard criteria by 125 of 126 companies (only 0.8% companies provided GHS information). For more detailed information, please visit ECHA C&L website.

ECHA C&L Notifications Summary

Aggregated GHS information provided per 126 reports by companies from 2 notifications to the ECHA C&L Inventory.

Reported as not meeting GHS hazard criteria per 125 of 126 reports by companies. For more detailed information, please visit ECHA C&L website.

There is 1 notification provided by 1 of 126 reports by companies with hazard statement code(s).

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

10.1.2 Hazard Classes and Categories

Not Classified

10.2 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: 2(3H)-Furanone, 5-(3-hexenyl)dihydro-5-methyl-, (E)-
The Australian Inventory of Industrial Chemicals
Chemical: 2(3H)-Furanone, 5-(3-hexenyl)dihydro-5-methyl-, (Z)-
New Zealand EPA Inventory of Chemical Status
2(3H)-Furanone, 5-(3Z)-3-hexenyldihydro-5-methyl-: Does not have an individual approval but may be used under an appropriate group standard

10.3 Other Safety Information

Chemical Assessment
IMAP assessments - 2(3H)-Furanone, 5-(3-hexenyl)dihydro-5-methyl-, (Z)-: Environment tier I assessment
Chemical Assessment
Evaluation - Chemicals not considered for in depth evaluation - Not commercially active in Australia

11 Literature

11.1 Consolidated References

11.2 Chemical Co-Occurrences in Literature

12 Patents

12.1 Depositor-Supplied Patent Identifiers

12.2 Chemical Co-Occurrences in Patents

12.3 Chemical-Gene Co-Occurrences in Patents

13 Classification

13.1 ChEBI Ontology

13.2 ChemIDplus

13.3 UN GHS Classification

13.4 NORMAN Suspect List Exchange Classification

13.5 EPA DSSTox Classification

13.6 EPA TSCA and CDR Classification

13.7 MolGenie Organic Chemistry Ontology

14 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
    2(3H)-Furanone, 5-(3-hexenyl)dihydro-5-methyl-, (Z)-
    https://services.industrialchemicals.gov.au/search-assessments/
    2(3H)-Furanone, 5-(3-hexenyl)dihydro-5-methyl-, (E)-
    https://services.industrialchemicals.gov.au/search-inventory/
  2. CAS Common Chemistry
    LICENSE
    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/
    2(3H)-Furanone, 5-(3-hexenyl)dihydro-5-methyl-, (E)-
    https://commonchemistry.cas.org/detail?cas_rn=14252-84-7
  3. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  4. EPA Chemicals under the TSCA
    2(3H)-Furanone, 5-(3Z)-3-hexen-1-yldihydro-5-methyl-
    https://www.epa.gov/chemicals-under-tsca
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  5. EPA DSSTox
    2(3H)-Furanone, 5-(3-hexenyl)dihydro-5-methyl-, (E)-
    https://comptox.epa.gov/dashboard/DTXSID701216879
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  6. European Chemicals Agency (ECHA)
    LICENSE
    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
    (Z)-5-hex-3-enyldihydro-5-methylfuran-2(3H)-one (EC: 274-942-8)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/20787
  7. Human Metabolome Database (HMDB)
    LICENSE
    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
    4-Hydroxy-4-methyl-7-decenoic acid gamma-lactone
    http://www.hmdb.ca/metabolites/HMDB0036191
  8. International Fragrance Association (IFRA)
    LICENSE
    (c) The International Fragrance Association, 2007-2021. All rights reserved.
    https://ifrafragrance.org/links/copyright
  9. New Zealand Environmental Protection Authority (EPA)
    LICENSE
    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/
  10. ChEBI
    4-Hydroxy-4-methyl-7-decenoic acid gamma-lactone
    https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:195884
  11. EU Food Improvement Agents
  12. Joint FAO/WHO Expert Committee on Food Additives (JECFA)
    LICENSE
    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
  13. FDA Substances Added to Food
    LICENSE
    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
  14. Flavor and Extract Manufacturers Association (FEMA)
  15. Japan Chemical Substance Dictionary (Nikkaji)
  16. Metabolomics Workbench
    4-Hydroxy-4-methyl-7-decenoic acid gamma-lactone
    https://www.metabolomicsworkbench.org/data/StructureData.php?RegNo=47252
  17. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
  18. SpectraBase
  19. PubChem
  20. GHS Classification (UNECE)
  21. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  22. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS