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gamma-BISABOLENE, (E)-

PubChem CID
5352437
Structure
gamma-BISABOLENE, (E)-_small.png
gamma-BISABOLENE, (E)-_3D_Structure.png
Molecular Formula
Synonyms
  • (E)-gamma-Bisabolene
  • 53585-13-0
  • gamma-Bisabolene, (E)-
  • gamma-Bisabolene, (4E)-
  • UNII-L8M7R52O3B
Molecular Weight
204.35 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-27
  • Modify:
    2025-01-18
Description
(E)-gamma-bisabolene is a gamma-bisabolene.
(E)-gamma-Bisabolene has been reported in Symphyopappus reticulatus, Helichrysum mimetes, and other organisms with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
gamma-BISABOLENE, (E)-.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(4E)-1-methyl-4-(6-methylhept-5-en-2-ylidene)cyclohexene
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8H,5,7,9-11H2,1-4H3/b15-14-
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

XBGUIVFBMBVUEG-PFONDFGASA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CC1=CC/C(=C(\C)/CCC=C(C)C)/CC1
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C15H24
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

495-62-5
53585-13-0
13062-00-5

2.3.2 Deprecated CAS

11003-31-9

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 HMDB ID

2.3.9 JECFA Number

1336

2.3.10 KEGG ID

2.3.11 Lipid Maps ID (LM_ID)

2.3.12 Metabolomics Workbench ID

2.3.13 Nikkaji Number

2.3.14 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
204.35 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
4.7
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
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
204.187800766 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
204.187800766 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
0 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
15
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
296
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
0
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 slightly viscous oil; pleasant, warm sweet-spicy-balsamic aroma

3.2.2 Boiling Point

280.00 to 281.00 °C. @ 760.00 mm Hg
The Good Scents Company Information System

3.2.3 Solubility

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

3.2.4 Density

0.850-0.858

3.2.5 Refractive Index

1.493-1.497

3.2.6 Kovats Retention Index

Standard non-polar
1523 , 1528 , 1521 , 1521 , 1520 , 1525 , 1524 , 1518 , 1531 , 1532 , 1528 , 1529 , 1515 , 1527 , 1531 , 1510 , 1528 , 1550 , 1482
Semi-standard non-polar
1538.4 , 1534 , 1523 , 1533 , 1539 , 1544 , 1535 , 1537 , 1535 , 1535 , 1533 , 1535 , 1517 , 1547 , 1535 , 1533 , 1520 , 1530 , 1532 , 1528 , 1538 , 1525 , 1538 , 1529 , 1531 , 1533 , 1528 , 1531 , 1535 , 1527 , 1527 , 1527 , 1531 , 1520 , 1533 , 1533 , 1539 , 1535 , 1537 , 1523 , 1527 , 1538 , 1515 , 1531 , 1577 , 1534 , 1531 , 1535 , 1531 , 1541 , 1533.1 , 1543.6 , 1533 , 1535 , 1515 , 1530 , 1531 , 1532 , 1527 , 1539 , 1535 , 1535
Standard polar
1727 , 1737 , 1737 , 1761 , 1766 , 1775 , 1761 , 1745 , 1745 , 1771 , 1766 , 1758 , 1790 , 1762 , 1773

3.3 SpringerMaterials Properties

3.4 Chemical Classes

3.4.1 Food Additives

ANTIMICROBIAL AGENT, FLAVOR ENHANCER, FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food

3.4.2 Fragrances

Fragrance Ingredient (Bisabolene) -> IFRA transparency List

3.4.3 Lipids

Lipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C15 isoprenoids (sesquiterpenes) [PR0103]

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 GC-MS

1 of 3
View All
NIST Number
412681
Library
Main library
Total Peaks
60
m/z Top Peak
93
m/z 2nd Highest
107
m/z 3rd Highest
135
Thumbnail
Thumbnail
2 of 3
View All
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

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

Floral

7.3 FDA Substances Added to Food

Substance
Used for (Technical Effect)
ANTIMICROBIAL AGENT, FLAVOR ENHANCER, FLAVORING AGENT OR ADJUVANT
FEMA Number
3331
GRAS Number
6, 25
JECFA Flavor Number
1336

7.4 Associated Foods

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

Chemical Name
BISABOLENE
Evaluation Year
2004
ADI
No safety concern at current levels of intake when used as a flavouring agent
Tox Monograph

8 Pharmacology and Biochemistry

8.1 Human Metabolite Information

8.1.1 Cellular Locations

  • Extracellular
  • Membrane

8.2 Biochemical Reactions

9 Use and Manufacturing

9.1 Uses

9.1.1 Use Classification

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

9.2 General Manufacturing Information

EPA TSCA Commercial Activity Status
Cyclohexene, 4-(1,5-dimethyl-4-hexen-1-ylidene)-1-methyl-: ACTIVE

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

Note
Pictograms displayed are for 99.8% (1715 of 1718) of reports that indicate hazard statements. This chemical does not meet GHS hazard criteria for 0.2% (3 of 1718) of reports.
Pictogram(s)
Irritant
Health Hazard
Signal
Danger
GHS Hazard Statements

H304 (99.8%): May be fatal if swallowed and enters airways [Danger Aspiration hazard]

H315 (99.8%): Causes skin irritation [Warning Skin corrosion/irritation]

H317 (99.8%): May cause an allergic skin reaction [Warning Sensitization, Skin]

Precautionary Statement Codes

P261, P264, P272, P280, P301+P316, P302+P352, P321, P331, P332+P317, P333+P317, P362+P364, P405, 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 1718 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria per 3 of 1718 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 6 notifications provided by 1715 of 1718 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

Asp. Tox. 1 (99.8%)

Skin Irrit. 2 (99.8%)

Skin Sens. 1 (99.8%)

10.2 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: Cyclohexene, 4-(1,5-dimethyl-4-hexenylidene)-1-methyl-
New Zealand EPA Inventory of Chemical Status
Cyclohexene, 4-(1,5-dimethyl-4-hexenylidene)-1-methyl-: Does not have an individual approval but may be used under an appropriate group standard

11 Literature

11.1 Consolidated References

11.2 Springer Nature References

11.3 Thieme References

11.4 Chemical Co-Occurrences in Literature

11.5 Chemical-Gene Co-Occurrences in Literature

11.6 Chemical-Disease Co-Occurrences in Literature

12 Patents

12.1 Depositor-Supplied Patent Identifiers

12.2 Chemical Co-Occurrences in Patents

12.3 Chemical-Disease Co-Occurrences in Patents

12.4 Chemical-Gene Co-Occurrences in Patents

13 Interactions and Pathways

13.1 Pathways

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 KEGG: Lipid

15.4 KEGG: Phytochemical Compounds

15.5 ChemIDplus

15.6 UN GHS Classification

15.7 NORMAN Suspect List Exchange Classification

15.8 EPA DSSTox Classification

15.9 EPA TSCA and CDR Classification

15.10 LOTUS Tree

15.11 MolGenie Organic Chemistry Ontology

16 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
    Cyclohexene, 4-(1,5-dimethyl-4-hexenylidene)-1-methyl-
    https://services.industrialchemicals.gov.au/search-inventory/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. EPA Chemicals under the TSCA
    Cyclohexene, 4-(1,5-dimethyl-4-hexen-1-ylidene)-1-methyl-
    https://www.epa.gov/chemicals-under-tsca
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  4. EPA DSSTox
    (4E)-1-Methyl-4-(6-methyl-5-hepten-2-ylidene)cyclohexene
    https://comptox.epa.gov/dashboard/DTXSID101037435
    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
    2-methyl-6-(4-methylcyclohex-3-en-1-ylidene)hept-2-ene
    https://echa.europa.eu/substance-information/-/substanceinfo/100.007.097
    2-methyl-6-(4-methylcyclohex-3-en-1-ylidene)hept-2-ene (EC: 207-805-8)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/58750
  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. 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
  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
  11. 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/
  12. EU Food Improvement Agents
  13. 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
  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. FooDB
    LICENSE
    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
    (Z)-2,6,10-Bisabolatriene
    https://foodb.ca/compounds/FDB015005
    (E)-2,6,10-Bisabolatriene
    https://foodb.ca/compounds/FDB021729
  17. Japan Chemical Substance Dictionary (Nikkaji)
  18. KEGG
    LICENSE
    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
  19. KNApSAcK Species-Metabolite Database
  20. Natural Product Activity and Species Source (NPASS)
  21. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  22. Metabolomics Workbench
  23. 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
    (E)-1-Methyl-4-(6-methylhept-5-en-2-ylidene)cyclohex-1-ene
    http://www.nist.gov/srd/nist1a.cfm
  24. SpectraBase
  25. Rhea - Annotated Reactions Database
    LICENSE
    Rhea has chosen to apply the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/). This means that you are free to copy, distribute, display and make commercial use of the database in all legislations, provided you credit (cite) Rhea.
    https://www.rhea-db.org/help/license-disclaimer
  26. Springer Nature
  27. SpringerMaterials
    4-(1,5-dimethyl-4-hexenylidene)-1-methylcyclohexene
    https://materials.springer.com/substanceprofile/docs/smsid_haittvgcqowxpwwz
  28. 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/
  29. Wikidata
  30. PubChem
  31. GHS Classification (UNECE)
  32. 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/
  33. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS