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(-)-Fenchone

PubChem CID
82229
Structure
(-)-Fenchone_small.png
(-)-Fenchone_3D_Structure.png
(-)-Fenchone__Crystal_Structure.png
Molecular Formula
Synonyms
  • EINECS 232-107-5
  • ( -)-Fenchone
  • (-)-1,3,3-Trimethyl-2-norbornanone
  • (1R)-(-)-Fenchone
  • (1R,4S)-(-)-Fenchone
Molecular Weight
152.23 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-07-10
  • Modify:
    2024-12-07
Description
(1R,4S)-fenchone is a fenchone that has (1R,4S)-stereochemistry. It is a constituent of the essential oils obtained from fennel. It has a role as a plant metabolite. It is an enantiomer of a (1S,4R)-fenchone.
(-)-Fenchone has been reported in Magnolia officinalis and Thuja occidentalis with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
(-)-Fenchone.png

1.2 3D Conformer

1.3 Crystal Structures

1 of 2
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CCDC Number
Crystal Structure Data
Crystal Structure Depiction
Crystal Structure Depiction

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1R,4S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-one
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C10H16O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7H,4-6H2,1-3H3/t7-,10+/m0/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

LHXDLQBQYFFVNW-OIBJUYFYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C[C@@]12CC[C@@H](C1)C(C2=O)(C)C
Computed by OEChem 2.3.0 (PubChem release 2021.10.14)

2.2 Molecular Formula

C10H16O
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

1195-79-5

2.3.2 Deprecated CAS

1071582-04-1, 126-21-6, 18492-37-0
11000-29-6, 1421788-37-5, 1822335-31-8, 1980023-27-5, 2180102-04-7, 2308507-23-3, 2566622-27-1

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 ChEBI ID

2.3.6 DSSTox Substance ID

2.3.7 FEMA Number

2.3.8 JECFA Number

2200

2.3.9 Lipid Maps ID (LM_ID)

2.3.10 Metabolomics Workbench ID

2.3.11 Nikkaji Number

2.3.12 Wikidata

2.4 Synonyms

2.4.1 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
152.23 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
2.3
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
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
152.120115130 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
152.120115130 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
17.1Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
11
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
217
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
2
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
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

Clear colorless to pale yellow liquid, Camphor herbal earthy woody aroma

3.2.2 Solubility

Practically insoluble to insoluble
Soluble (in ethanol)

3.2.3 Density

0.941-0.946

3.2.4 Refractive Index

1.461-1.465

3.3 Chemical Classes

3.3.1 Food Additives

FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food

3.3.2 Fragrances

Fragrance Ingredient (l-Fenchone) -> IFRA transparency List

3.3.3 Lipids

Lipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C10 isoprenoids (monoterpenes) [PR0102]

4 Spectral Information

4.1 1D NMR Spectra

1D NMR Spectra

4.1.1 1H NMR Spectra

1 of 2
Instrument Name
Varian CFT-20
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Instrument Name
Varian CFT-20
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.1.2 13C NMR Spectra

1 of 2
Source of Sample
Aldrich Chemical Company, Inc., Milwaukee, Wisconsin
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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2 of 2
Source of Sample
Tokyo Kasei Kogyo Company, Ltd., Tokyo, Japan
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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4.1.3 17O NMR Spectra

Copyright
Copyright © 2016-2024 W. Robien, Inst. of Org. Chem., Univ. of Vienna. All Rights Reserved.
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4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 3
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MoNA ID
MS Category
Experimental
MS Type
GC-MS
MS Level
MS1
Instrument
HITACHI RMU-6M
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

81 99.99

152 27.53

69 20.61

80 15.63

82 8.41

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License
CC BY-NC-SA
2 of 3
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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.
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4.3 IR Spectra

4.3.1 FTIR Spectra

1 of 2
Technique
CAPILLARY CELL: NEAT
Source of Sample
Aldrich Chemical Company, Inc., Milwaukee, Wisconsin
Catalog Number
19643
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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2 of 2
Instrument Name
Bruker Tensor 27 FT-IR
Technique
Neat
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
Alfa Aesar, Thermo Fisher Scientific
Catalog Number
L15151
Lot Number
10117689
Copyright
Copyright © 2016-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.3.2 ATR-IR Spectra

1 of 2
Instrument Name
Bruker Tensor 27 FT-IR
Technique
ATR-Neat (DuraSamplIR II)
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
Alfa Aesar, Thermo Fisher Scientific
Catalog Number
L15151
Lot Number
10117689
Copyright
Copyright © 2016-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Source of Sample
Aldrich
Catalog Number
196436
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.3.3 Vapor Phase IR Spectra

1 of 2
Instrument Name
DIGILAB FTS-14
Technique
Vapor Phase
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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2 of 2
Technique
Vapor Phase
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Aldrich
Catalog Number
196436
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.4 Raman Spectra

1 of 2
Instrument Name
Bruker MultiRAM Stand Alone FT-Raman Spectrometer
Technique
FT-Raman
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
Alfa Aesar, Thermo Fisher Scientific
Catalog Number
L15151
Lot Number
10117689
Copyright
Copyright © 2016-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Catalog Number
196436
Copyright
Copyright © 2017-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2017-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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6 Chemical Vendors

7 Food Additives and Ingredients

7.1 Food Additive Classes

Flavoring Agents
JECFA Functional Classes
FLAVOURING_AGENT;

7.2 FEMA Flavor Profile

Floral

7.3 FDA Substances Added to Food

Substance
Used for (Technical Effect)
FLAVORING AGENT OR ADJUVANT
FEMA Number
4519
GRAS Number
24
JECFA Flavor Number
2200

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

Chemical Name
L-FENCHONE
Evaluation Year
2014
ADI
No safety concern at current levels of intake when used as a flavouring agent

8 Use and Manufacturing

8.1 Uses

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

8.1.1 Use Classification

Fragrance Ingredients
Flavoring Agents -> JECFA Flavorings Index
FLAVOURING_AGENT; -> JECFA Functional Classes

8.2 General Manufacturing Information

EPA TSCA Commercial Activity Status
Bicyclo[2.2.1]heptan-2-one, 1,3,3-trimethyl-, (1R,4S)-: ACTIVE

9 Safety and Hazards

9.1 Hazards Identification

9.1.1 GHS Classification

1 of 2
View All
Note
This chemical does not meet GHS hazard criteria for 84.8% (284 of 335) of all reports. Pictograms displayed are for 15.2% (51 of 335) of reports that indicate hazard statements.
Pictogram(s)
Flammable
Signal
Warning
GHS Hazard Statements
H226 (14%): Flammable liquid and vapor [Warning Flammable liquids]
Precautionary Statement Codes

P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 335 reports by companies from 3 notifications to the ECHA C&L Inventory.

Reported as not meeting GHS hazard criteria per 284 of 335 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 2 notifications provided by 51 of 335 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.

9.1.2 Hazard Classes and Categories

Flam. Liq. 3 (14%)
Flam. Liq. 3 (13%)

9.2 Regulatory Information

REACH Registered Substance
REACH Registered Substance
New Zealand EPA Inventory of Chemical Status
Bicyclo2.2.1heptan-2-one, 1,3,3-trimethyl-, (1R,4S)-: Does not have an individual approval but may be used under an appropriate group standard

10 Toxicity

10.1 Toxicological Information

10.1.1 Acute Effects

11 Literature

11.1 Consolidated References

11.2 Springer Nature References

11.3 Thieme References

11.4 Wiley References

11.5 Chemical Co-Occurrences in Literature

11.6 Chemical-Gene Co-Occurrences in Literature

11.7 Chemical-Disease Co-Occurrences in Literature

12 Patents

12.1 Depositor-Supplied Patent Identifiers

12.2 WIPO PATENTSCOPE

12.3 Chemical Co-Occurrences in Patents

12.4 Chemical-Disease Co-Occurrences in Patents

13 Biological Test Results

13.1 BioAssay Results

14 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

15 Classification

15.1 ChEBI Ontology

15.2 LIPID MAPS Classification

15.3 ChemIDplus

15.4 UN GHS Classification

15.5 EPA CPDat Classification

15.6 NORMAN Suspect List Exchange Classification

15.7 EPA DSSTox Classification

15.8 EPA TSCA and CDR Classification

15.9 LOTUS Tree

15.10 EPA Substance Registry Services Tree

15.11 MolGenie Organic Chemistry Ontology

16 Information Sources

  1. 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. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. EPA Chemicals under the TSCA
    Bicyclo[2.2.1]heptan-2-one, 1,3,3-trimethyl-, (1R,4S)-
    https://www.epa.gov/chemicals-under-tsca
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  4. EPA DSSTox
    Bicyclo[2.2.1]heptan-2-one, 1,3,3-trimethyl-, (1R,4S)-
    https://comptox.epa.gov/dashboard/DTXSID30884431
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  5. 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
    3,3-dimethyl-8,9-dinorbornan-2-one
    https://chem.echa.europa.eu/100.013.458
    1,3,3-trimethylnorbornan-2-one
    https://chem.echa.europa.eu/100.029.188
  6. FDA Global Substance Registration System (GSRS)
    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
  7. International Fragrance Association (IFRA)
    LICENSE
    (c) The International Fragrance Association, 2007-2021. All rights reserved.
    https://ifrafragrance.org/links/copyright
  8. 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/
  9. ChEBI
  10. LOTUS - the natural products occurrence database
    LICENSE
    The code for LOTUS is released under the GNU General Public License v3.0.
    https://lotus.nprod.net/
  11. Crystallography Open Database (COD)
    LICENSE
    All data in the COD and the database itself are dedicated to the public domain and licensed under the CC0 License. Users of the data should acknowledge the original authors of the structural data.
    https://creativecommons.org/publicdomain/zero/1.0/
  12. The Cambridge Structural Database
  13. EPA Chemical and Products Database (CPDat)
    Bicyclo[2.2.1]heptan-2-one, 1,3,3-trimethyl-, (1R,4S)-
    https://comptox.epa.gov/dashboard/DTXSID30884431#exposure
  14. 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
  15. Flavor and Extract Manufacturers Association (FEMA)
  16. 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
  17. Japan Chemical Substance Dictionary (Nikkaji)
  18. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  19. Natural Product Activity and Species Source (NPASS)
  20. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  21. SpectraBase
    1,3,3-TRIMETHYL-BICYCLO-[2.2.1]-HEPTAN-2-ONE
    https://spectrabase.com/spectrum/1eb38wkPN8m
    1-1,3,3-TRIMETHYL-2-NORBORNANONE
    https://spectrabase.com/spectrum/ENUHK7DOtZI
    L-(-)-1,3,3-TRIMETHYL-2-NORBORNANONE
    https://spectrabase.com/spectrum/6cnTDJxRKgp
    (-)-1,3,3-trimethyl-2-norbornanone
    https://spectrabase.com/spectrum/4jAh91YKLCu
    L-1,3,3-trimethyl-2-norbornanone
    https://spectrabase.com/spectrum/I4huR09zfhx
    L-1,3,3-TRIMETHYL-2-NORBORNANONE
    https://spectrabase.com/spectrum/KB6bDIAagT4
    2-NORBORNANONE, 1,3,3-TRIMETHYL-, L-/MINUS/-,
    https://spectrabase.com/spectrum/1Qiddz89bAs
  22. Metabolomics Workbench
  23. NMRShiftDB
  24. Springer Nature
  25. Thieme Chemistry
    LICENSE
    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/
  26. Wikidata
  27. Wiley
  28. PubChem
  29. GHS Classification (UNECE)
  30. 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/
  31. EPA Substance Registry Services
  32. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  33. PATENTSCOPE (WIPO)
CONTENTS