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9,11-Octadecadienoic acid

PubChem CID
5282796
Structure
9,11-Octadecadienoic acid_small.png
9,11-Octadecadienoic acid_3D_Structure.png
Molecular Formula
Synonyms
  • Isolinoleic acid
  • 544-71-8
  • 9,11-Octadecadienoic acid
  • Conjugated linoleic acid
  • Ricineic acid
Molecular Weight
280.4 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2004-09-16
  • Modify:
    2025-01-18
Description
(9E,11E)-octadecadienoic acid is an octadeca-9,11-dienoic acid having 9-trans,11-trans-stereochemistry. It has a role as an apoptosis inducer, an antineoplastic agent, an anti-inflammatory agent, an antiatherogenic agent, a bacterial xenobiotic metabolite and a human metabolite. It is a conjugate acid of a (9E,11E)-octadecadienoate.
9,11-Octadecadienoic acid has been reported in Brassica napus with data available.
Conjugated Linoleic Acid is a slightly altered form of linoleic acid, which is an omega-6 fatty acid important to human health. It is found in beef and dairy fats.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
9,11-Octadecadienoic acid.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(9E,11E)-octadeca-9,11-dienoic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h7-10H,2-6,11-17H2,1H3,(H,19,20)/b8-7+,10-9+
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

JBYXPOFIGCOSSB-XBLVEGMJSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CCCCCC/C=C/C=C/CCCCCCCC(=O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C18H32O2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

1839-11-8
544-71-8

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEBI ID

2.3.5 ChEMBL ID

2.3.6 DSSTox Substance ID

2.3.7 HMDB ID

2.3.8 Lipid Maps ID (LM_ID)

2.3.9 Metabolomics Workbench ID

2.3.10 NCI Thesaurus Code

2.3.11 Nikkaji Number

2.3.12 RXCUI

2.3.13 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
280.4 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
7.1
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
1
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
14
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
280.240230259 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
280.240230259 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
37.3 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
20
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
267
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
2
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

Liquid

3.3 Chemical Classes

3.3.1 Cosmetics

Cosmetic ingredients (Isomerized Linoleic Acid) -> CIR (Cosmetic Ingredient Review)

3.3.2 Lipids

Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Unsaturated fatty acids [FA0103]

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 MS-MS

1 of 6
View All
Spectra ID
Ionization Mode
Positive
Top 5 Peaks

279.2344 100

280.2372 18.12

Thumbnail
Thumbnail
2 of 6
View All
Spectra ID
Ionization Mode
Positive
Top 5 Peaks

279.2345 100

280.2377 16.02

Thumbnail
Thumbnail

4.1.2 LC-MS

1 of 8
View All
Accession ID
Authors
Plant Biology, The Noble Foundation, Ardmore, OK, US/Dennis Fine, Daniel Wherritt, and Lloyd Sumner
Instrument
Bruker impact HD
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
NEGATIVE
Ionization
ESI
Collision Energy
20 eV
Column Name
Waters Acquity BEH C18 1.7um x 2.1 x 150 mm
Retention Time
1852.8 sec
Precursor m/z
279.2344
Precursor Adduct
[M-H]-
Top 5 Peaks

279.2344 999

280.2372 181

Thumbnail
Thumbnail
License
CC BY-NC-SA
2 of 8
View All
Accession ID
Authors
Plant Biology, The Noble Foundation, Ardmore, OK, US/Dennis Fine, Daniel Wherritt, and Lloyd Sumner
Instrument
Bruker impact HD
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
NEGATIVE
Ionization
ESI
Collision Energy
10 eV
Column Name
Waters Acquity BEH C18 1.7um x 2.1 x 150 mm
Retention Time
1852.8 sec
Precursor m/z
279.2345
Precursor Adduct
[M-H]-
Top 5 Peaks

279.2345 999

280.2377 160

Thumbnail
Thumbnail
License
CC BY-NC-SA

6 Chemical Vendors

7 Drug and Medication Information

7.1 Clinical Trials

7.1.1 ClinicalTrials.gov

8 Food Additives and Ingredients

8.1 Associated Foods

9 Pharmacology and Biochemistry

9.1 Human Metabolite Information

9.1.1 Cellular Locations

  • Extracellular
  • Membrane

9.2 Biochemical Reactions

10 Use and Manufacturing

10.1 Uses

Cosmetic Ingredient Review Link
CIR ingredient: Isomerized Linoleic Acid

10.2 General Manufacturing Information

EPA TSCA Commercial Activity Status
9,11-Octadecadienoic acid: ACTIVE

11 Safety and Hazards

11.1 Regulatory Information

New Zealand EPA Inventory of Chemical Status
9,11-Octadecadienoic acid: Does not have an individual approval but may be used under an appropriate group standard

12 Associated Disorders and Diseases

Disease
Lipid peroxidation
References
PubMed: 4075442
Disease
Primary biliary cirrhosis
References

13 Literature

13.1 Consolidated References

13.2 Springer Nature References

13.3 Chemical Co-Occurrences in Literature

13.4 Chemical-Gene Co-Occurrences in Literature

13.5 Chemical-Disease Co-Occurrences in Literature

14 Patents

14.1 Depositor-Supplied Patent Identifiers

14.2 WIPO PATENTSCOPE

14.3 Chemical Co-Occurrences in Patents

14.4 Chemical-Disease Co-Occurrences in Patents

14.5 Chemical-Gene Co-Occurrences in Patents

15 Interactions and Pathways

15.1 Chemical-Target Interactions

15.2 Pathways

16 Biological Test Results

16.1 BioAssay Results

17 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106
A metabolome atlas of the aging mouse brain. Nat Commun. 2021 Oct 15;12(1):6021. DOI:10.1038/s41467-021-26310-y. PMID:34654818; PMCID:PMC8519999.
The Metabolome Atlas of the Aging Mouse Brain: https://mouse.atlas.metabolomics.us

18 Classification

18.1 ChEBI Ontology

18.2 LIPID MAPS Classification

18.3 ChemIDplus

18.4 ChEMBL Target Tree

18.5 EPA DSSTox Classification

18.6 EPA TSCA and CDR Classification

18.7 LOTUS Tree

18.8 MolGenie Organic Chemistry Ontology

19 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
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  4. EPA DSSTox
    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
  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
    (9E,11E)-Octadecadienoic acid
    http://www.hmdb.ca/metabolites/HMDB0005047
  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. NCI Thesaurus (NCIt)
    LICENSE
    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
  12. ChEMBL
    LICENSE
    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
  13. ClinicalTrials.gov
    LICENSE
    The ClinicalTrials.gov data carry an international copyright outside the United States and its Territories or Possessions. Some ClinicalTrials.gov data may be subject to the copyright of third parties; you should consult these entities for any additional terms of use.
    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  14. Comparative Toxicogenomics Database (CTD)
    LICENSE
    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
  15. Cosmetic Ingredient Review (CIR)
  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
    9E,11E-Octadecadienoic acid
    https://foodb.ca/compounds/FDB023609
    10E,12Z-Octadecadienoic acid
    https://foodb.ca/compounds/FDB023610
  17. Japan Chemical Substance Dictionary (Nikkaji)
  18. KNApSAcK Species-Metabolite Database
  19. Natural Product Activity and Species Source (NPASS)
  20. West Coast Metabolomics Center-UC Davis
    FA 18:2; (linoleic acid)
  21. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  22. MassBank Europe
  23. 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
  24. Metabolomics Workbench
  25. NLM RxNorm Terminology
    LICENSE
    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
  26. Springer Nature
  27. Wikidata
    (9E,11E)-octadeca-9,11-dienoic acid
    https://www.wikidata.org/wiki/Q27160342
  28. PubChem
  29. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  30. PATENTSCOPE (WIPO)
CONTENTS