9,11-Octadecadienoic acid
PubChem CID
5282796
Structure
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.
Chemical Structure Depiction
(9E,11E)-octadeca-9,11-dienoic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)
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)
JBYXPOFIGCOSSB-XBLVEGMJSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
CCCCCC/C=C/C=C/CCCCCCCC(=O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)
C18H32O2
Computed by PubChem 2.2 (PubChem release 2021.10.14)
- Isolinoleic acid
- 544-71-8
- 9,11-Octadecadienoic acid
- Conjugated linoleic acid
- Ricineic acid
- 9E,11E-octadecadienoic acid
- (9E,11E)-octadeca-9,11-dienoic acid
- trans,trans-9,11-Octadecadienoicacid
- Nouracid DE 554
- Mangold's acid
- 9,11-Linoleic acid
- OCTADECA-9,11-DIENOIC ACID
- Ricinenic acid
- delta9,11-Octadecadienoic acid
- 9(E),11(E)-Conjugated Linoleic Acid
- 9(E),11(E)-Octadecadienoic acid
- K3BO6AJ7F7
- LinoleicAcid
- 9-trans,11-trans-Octadecadienoic acid
- 1839-11-8
- UNII-K3BO6AJ7F7
- 9,11-Octadecadienoic acid, (E,E)-
- trans-9, trans-11-octadecadienoic acid
- 9,11-Octadecadienoic acid, (9E,11E)-
- Conjugated linoleic acid (9Z,11E)
- Conjugated Linoleic Acid (9E,11E)
- C18:2n-7,9
- NSC 7886
- 9t,11t-CLA
- 9E,11E-CLA
- Selin CLA
- Conjugated (9E,11E)-Linoleic acid
- (9E,11E)-9,11-Octadecadienoic acid
- | cent-Eleostearic acid
- (E,E)-isolinoleic acid
- 9E, 11E-Linoleic acid
- 9-trans, 11-trans-CLA
- Delta9,11-Octadecadienoate
- SCHEMBL288695
- CLA 80
- CHEMBL4529739
- (9E,11E)-Octadecadienoic acid
- CHEBI:36025
- CHEBI:88464
- DTXSID60873030
- JBYXPOFIGCOSSB-XBLVEGMJSA-N
- Conjugated linoleic acid(9E,11E)
- (E,E)-9,11-Octadecadienoic Acid
- 9tr,11tr-OCTADECADIENOIC ACID
- LMFA01030119
- AKOS015911855
- trans,trans-9,11-octadecadienoic acid
- HY-113102A
- PD020527
- 9-trans,11-trans-conjugated linoleic acid
- DB-257125
- CS-0138297
- G90979
- A891827
- J-015983
- Q27116671
- Q27160342
- Conjugated (9E,11E)-Linoleic acid, analytical standard
Property Name
Property Value
Reference
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)
Liquid
Cosmetic ingredients (Isomerized Linoleic Acid) -> CIR (Cosmetic Ingredient Review)
Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Unsaturated fatty acids [FA0103]
Spectra ID
Ionization Mode
Positive
Top 5 Peaks
279.2344 100
280.2372 18.12
Spectra ID
Ionization Mode
Positive
Top 5 Peaks
279.2345 100
280.2377 16.02
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
License
CC BY-NC-SA
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
License
CC BY-NC-SA
Follow these links to do a live 2D search or do a live 3D search for this compound, sorted by annotation score. This section is deprecated (see here for details), but these live search links provide equivalent functionality to the table that was previously shown here.
Same Connectivity Count
Same Isotope Count
Same Parent, Connectivity Count
Same Parent, Isotope Count
Same Parent, Exact Count
Mixtures, Components, and Neutralized Forms Count
Similar Compounds (2D)
Similar Conformers (3D)
- Extracellular
- Membrane
Cosmetic Ingredient Review Link
CIR ingredient: Isomerized Linoleic Acid
EPA TSCA Commercial Activity Status
9,11-Octadecadienoic acid: ACTIVE
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
Disease
References
Patents are available for this chemical structure:
https://patentscope.wipo.int/search/en/result.jsf?inchikey=JBYXPOFIGCOSSB-XBLVEGMJSA-N
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
- CAS Common ChemistryLICENSEThe 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/Conjugated linoleic acidhttps://commonchemistry.cas.org/detail?cas_rn=121250-47-3
- ChemIDplusChemIDplus Chemical Information Classificationhttps://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
- EPA Chemicals under the TSCA9,11-Octadecadienoic acidhttps://www.epa.gov/chemicals-under-tscaEPA TSCA Classificationhttps://www.epa.gov/tsca-inventory
- EPA DSSToxIsolinoleic acidhttps://comptox.epa.gov/dashboard/DTXSID60873030CompTox Chemicals Dashboard Chemical Listshttps://comptox.epa.gov/dashboard/chemical-lists/
- European Chemicals Agency (ECHA)LICENSEUse 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-notice9,11-Octadecadienoic acidhttps://echa.europa.eu/substance-information/-/substanceinfo/100.110.794
- FDA Global Substance Registration System (GSRS)LICENSEUnless 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#linkingISOLINOLEIC ACIDhttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/K3BO6AJ7F7
- Human Metabolome Database (HMDB)LICENSEHMDB 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 acidhttp://www.hmdb.ca/metabolites/HMDB0005047HMDB0005047_msms_2256472https://hmdb.ca/metabolites/HMDB0005047#spectra
- New Zealand Environmental Protection Authority (EPA)LICENSEThis work is licensed under the Creative Commons Attribution-ShareAlike 4.0 International licence.https://www.epa.govt.nz/about-this-site/general-copyright-statement/
- ChEBI(9E,11E)-octadecadienoic acidhttps://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:88464
- LOTUS - the natural products occurrence databaseLICENSEThe code for LOTUS is released under the GNU General Public License v3.0.https://lotus.nprod.net/9,11-Octadecadienoic acidhttps://www.wikidata.org/wiki/Q27160342LOTUS Treehttps://lotus.naturalproducts.net/
- NCI Thesaurus (NCIt)LICENSEUnless 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
- ChEMBLLICENSEAccess 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.htmlChEMBL Protein Target Treehttps://www.ebi.ac.uk/chembl/g/#browse/targets
- ClinicalTrials.govLICENSEThe 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
- Comparative Toxicogenomics Database (CTD)LICENSEIt 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.jsp9,11-linoleic acidhttps://ctdbase.org/detail.go?type=chem&acc=C046938Linoleic Acids, Conjugatedhttps://ctdbase.org/detail.go?type=chem&acc=D044243
- Cosmetic Ingredient Review (CIR)
- FooDBLICENSEFooDB 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/about9E,11E-Octadecadienoic acidhttps://foodb.ca/compounds/FDB02360910E,12Z-Octadecadienoic acidhttps://foodb.ca/compounds/FDB023610
- Japan Chemical Substance Dictionary (Nikkaji)
- KNApSAcK Species-Metabolite Database
- Natural Product Activity and Species Source (NPASS)
- West Coast Metabolomics Center-UC DavisFA 18:2; (linoleic acid)
- LIPID MAPSLipid Classificationhttps://www.lipidmaps.org/
- MassBank Europe9E, 11E-Linoleic acidhttps://massbank.eu/MassBank/Result.jsp?inchikey=JBYXPOFIGCOSSB-XBLVEGMJSA-N
- MassBank of North America (MoNA)LICENSEThe content of the MoNA database is licensed under CC BY 4.0.https://mona.fiehnlab.ucdavis.edu/documentation/license
- Metabolomics Workbench
- NLM RxNorm TerminologyLICENSEThe 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.htmllinoleic acids, conjugatedhttps://rxnav.nlm.nih.gov/id/rxnorm/382272
- Springer Nature
- Wikidata(9E,11E)-octadeca-9,11-dienoic acidhttps://www.wikidata.org/wiki/Q27160342
- PubChem
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
- PATENTSCOPE (WIPO)SID 403426835https://pubchem.ncbi.nlm.nih.gov/substance/403426835
CONTENTS