Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2022-03-07 02:49:25 UTC |
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HMDB ID | HMDB0005047 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | (9E,11E)-Octadecadienoic acid |
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Description | Conjugated linoleic acid is an integral term for the mixture of positional and geometrical isomers of the octadecadienoic acids, whose two double-bonds are separated with one single-bond. The most common isomers are cis-9, trans-11, and trans-10, cis-12. Conjugated linoleic acid is present in the food namely in the red meat and dairy products which the contemporary dietary recommendations tend to limit. Those limitations should be compensated with dietary supplements. Much attention has focused on the therapeutic potential of conjugated linoleic acid. Initial animal studies associated conjugated linoleic acid with beneficial health properties, such as reducing the risk of cancer, diabetes, atherosclerosis, inflammation and obesity. More recent human conjugated linoleic acid supplementation studies have often shown conflicting and less convincing health benefits. The marked variation between studies may reflect the isomer-specific effect of the individual conjugated linoleic acid isomers, which can often have opposing effects. Detrimental effects have been observed in some studies, in particular after supplementation with the trans-10,cis-12 conjugated linoleic acid isomer. Diet composition may modulate CLA effects on body fat accumulation. As far as human studies are concerned, a specific dietary pattern has not been established. As a result differences among studies and also among subjects in the same study are likely. In rodents, the effects of CLA vary with genotype, suggesting that genetic predisposition to fat accumulation can play an important role in the effectiveness of CLA. Human volunteers with different body mass index have participated in the published studies and even in the same experiment. So, differences in lipid metabolism among subjects could help to explain the discrepancies observed in the literature. Age and maturity may also be crucial. (PMID: 17053429 , 17217167 , 17554969 , 16477173 ). |
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Structure | CCCCCC\C=C\C=C\CCCCCCCC(O)=O 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+ |
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Synonyms | Value | Source |
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(9E,11E)-9,11-Octadecadienoic acid | ChEBI | (e,e)-9,11-Octadecadienoic acid | ChEBI | (e,e)-Isolinoleic acid | ChEBI | 9-trans, 11-trans-CLA | ChEBI | 9-trans,11-trans-Conjugated linoleic acid | ChEBI | 9-trans,11-trans-Octadecadienoic acid | ChEBI | 9E,11E-CLA | ChEBI | 9t,11t-CLA | ChEBI | Conjugated (9E,11E)-linoleic acid | ChEBI | Isolinoleic acid | ChEBI | Mangold's acid | ChEBI | trans,trans-9,11-Octadecadienoic acid | ChEBI | trans-9, trans-11-Octadecadienoic acid | ChEBI | (9E,11E)-9,11-Octadecadienoate | Generator | (e,e)-9,11-Octadecadienoate | Generator | (e,e)-Isolinoleate | Generator | 9-trans,11-trans-Conjugated linoleate | Generator | 9-trans,11-trans-Octadecadienoate | Generator | Conjugated (9E,11E)-linoleate | Generator | Isolinoleate | Generator | trans,trans-9,11-Octadecadienoate | Generator | trans-9, trans-11-Octadecadienoate | Generator | (9E,11E)-Octadecadienoate | Generator | 9,11-Linoleic acid | HMDB, MeSH | CLA 80 | HMDB | Conjugated linoleic acid | HMDB | delta9,11-Octadecadienoate | HMDB | Nouracid de 554 | HMDB | Ricineic acid | HMDB | Ricinenic acid | HMDB | Selin cla | HMDB | 9,11-Linoleic acid, (E,E)-isomer | MeSH, HMDB | 9,11-Isolinoleic acid | MeSH, HMDB | Octadeca-9,11-dienoic acid | MeSH, HMDB | 9,11-Octadecadienoate | MeSH, HMDB | (9E,11E)-Octadecadienoic acid | HMDB | 9,11-Conjugated linoleic acid | HMDB | 9-trans,11-trans-Linoleic acid | HMDB | 9E,11E-Octadecadienoic acid | HMDB | FA(18:2(9E,11E)) | HMDB | delta9,11-Octadecadienoic acid | HMDB | trans-11-trans-9-Octadecadienoic acid | HMDB | trans-9,trans-11 Conjugated linoleic acid | HMDB | trans-9,trans-11-Octadecadienoic acid | HMDB | Δ9,11-Octadecadienoic acid | HMDB | 9E,11E-Octadecadienoate | Generator | 10E,12Z-Octadecadienoate | Generator |
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Chemical Formula | C18H32O2 |
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Average Molecular Weight | 280.4455 |
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Monoisotopic Molecular Weight | 280.240230268 |
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IUPAC Name | (9E,11E)-octadeca-9,11-dienoic acid |
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Traditional Name | 9E,11E-octadecadienoic acid |
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CAS Registry Number | 1839-11-8 |
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SMILES | CCCCCC\C=C\C=C\CCCCCCCC(O)=O |
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InChI Identifier | 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+ |
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InChI Key | JBYXPOFIGCOSSB-XBLVEGMJSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Fatty Acyls |
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Sub Class | Lineolic acids and derivatives |
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Direct Parent | Lineolic acids and derivatives |
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Alternative Parents | |
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Substituents | - Octadecanoid
- Long-chain fatty acid
- Fatty acid
- Unsaturated fatty acid
- Straight chain fatty acid
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | |
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Disposition | |
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Process | |
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Role | |
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Physical Properties |
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State | Liquid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized | Show more...
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - (9E,11E)-Octadecadienoic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-052f-9550000000-f91f775c11691e572339 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (9E,11E)-Octadecadienoic acid GC-MS (1 TMS) - 70eV, Positive | splash10-0079-9531000000-ff0f0a6283e777000b03 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (9E,11E)-Octadecadienoic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - (9E,11E)-Octadecadienoic acid ESI-TOF 20V, Negative-QTOF | splash10-004i-0090000000-d3517fc9c425686f3f47 | 2017-09-12 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - (9E,11E)-Octadecadienoic acid ESI-TOF 10V, Negative-QTOF | splash10-004i-0090000000-dfad2b4819a8e09aeb74 | 2017-09-12 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - (9E,11E)-Octadecadienoic acid ESI-TOF 10V, Negative-QTOF | splash10-004i-0093020000-3713e3e16e9fc8ff9d4e | 2017-09-12 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - (9E,11E)-Octadecadienoic acid ESI-TOF 30V, Negative-QTOF | splash10-004i-0090000000-1ab95baf25a47f7edbbe | 2017-09-12 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - (9E,11E)-Octadecadienoic acid ESI-TOF , Negative-QTOF | splash10-004i-0091000000-88b67552039f5c14c7ea | 2017-09-12 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - (9E,11E)-Octadecadienoic acid LC-ESI-TOF , negative-QTOF | splash10-004i-0090000000-d3517fc9c425686f3f47 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - (9E,11E)-Octadecadienoic acid LC-ESI-TOF , negative-QTOF | splash10-004i-0090000000-dfad2b4819a8e09aeb74 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - (9E,11E)-Octadecadienoic acid LC-ESI-TOF , negative-QTOF | splash10-004i-0090000000-1ab95baf25a47f7edbbe | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - (9E,11E)-Octadecadienoic acid 20V, Positive-QTOF | splash10-004i-0090000000-d3517fc9c425686f3f47 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - (9E,11E)-Octadecadienoic acid 10V, Positive-QTOF | splash10-004i-0090000000-dfad2b4819a8e09aeb74 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - (9E,11E)-Octadecadienoic acid 30V, Positive-QTOF | splash10-004i-0090000000-1ab95baf25a47f7edbbe | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (9E,11E)-Octadecadienoic acid 10V, Positive-QTOF | splash10-03di-0090000000-f2c6c9de24118516f0db | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (9E,11E)-Octadecadienoic acid 20V, Positive-QTOF | splash10-022j-5690000000-f4c090f44fe34f660b19 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (9E,11E)-Octadecadienoic acid 40V, Positive-QTOF | splash10-006x-9830000000-42ee75da80e6ee682b90 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (9E,11E)-Octadecadienoic acid 10V, Negative-QTOF | splash10-004i-0090000000-f1e9e4b543f7d4f48bf8 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (9E,11E)-Octadecadienoic acid 20V, Negative-QTOF | splash10-01ti-0090000000-665523c6142ff4e39c96 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (9E,11E)-Octadecadienoic acid 40V, Negative-QTOF | splash10-0a4l-9230000000-b43315d97b9995f922a3 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (9E,11E)-Octadecadienoic acid 10V, Positive-QTOF | splash10-01qa-5590000000-6740409ad0ee9d0c387c | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (9E,11E)-Octadecadienoic acid 20V, Positive-QTOF | splash10-05mk-9510000000-78bd3b0ecfca1dab2bac | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (9E,11E)-Octadecadienoic acid 40V, Positive-QTOF | splash10-0apm-9000000000-98f6af2debd76c0c3c6e | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (9E,11E)-Octadecadienoic acid 10V, Negative-QTOF | splash10-004i-0090000000-03fd7d53d39127d02766 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (9E,11E)-Octadecadienoic acid 20V, Negative-QTOF | splash10-01t9-1090000000-c03baa3d5c1c48e8c45c | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (9E,11E)-Octadecadienoic acid 40V, Negative-QTOF | splash10-0006-9310000000-07f427d77d98dab09f40 | 2021-09-24 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | - Extracellular
- Membrane (predicted from logP)
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 19.3 +/- 3.9 uM | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected and Quantified | 25.3 +/- 1.1 uM | Adult (>18 years old) | Both | Lipid peroxidation | | details | Blood | Detected and Quantified | 24.0 +/- 11.0 uM | Adult (>18 years old) | Both | Primary biliary Cirrhosis | | details |
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Associated Disorders and Diseases |
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Disease References | Lipid peroxidation |
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- Thompson S, Smith MT: Measurement of the diene conjugated form of linoleic acid in plasma by high performance liquid chromatography: a questionable non-invasive assay of free radical activity? Chem Biol Interact. 1985 Nov;55(3):357-66. [PubMed:4075442 ]
| Primary biliary cirrhosis |
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- Braganza JM, Day JP: Serum octadeca-9-11 dienoic acid concentrations in primary biliary cirrhosis. Lancet. 1987 Apr 25;1(8539):987. [PubMed:2882386 ]
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Associated OMIM IDs | - 109720 (Primary biliary cirrhosis)
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB023610 |
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KNApSAcK ID | C00053367 |
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Chemspider ID | 4445923 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 5282796 |
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PDB ID | Not Available |
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ChEBI ID | 88464 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Priester, Remmet. 9,11-Octadecadienoic acid. (1939), US 2156737 19390502 CAN 33:44507 AN 1939:44507 |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Toomey S, McMonagle J, Roche HM: Conjugated linoleic acid: a functional nutrient in the different pathophysiological components of the metabolic syndrome? Curr Opin Clin Nutr Metab Care. 2006 Nov;9(6):740-7. [PubMed:17053429 ]
- Navarro V, Fernandez-Quintela A, Churruca I, Portillo MP: The body fat-lowering effect of conjugated linoleic acid: a comparison between animal and human studies. J Physiol Biochem. 2006 Jun;62(2):137-47. [PubMed:17217167 ]
- Tvrzicka E, Vecka M, Zak A: [Conjugated linoleic acid--the dietary supplement in the prevention of cardiovascular diseases]. Cas Lek Cesk. 2007;146(5):459-65. [PubMed:17554969 ]
- Tricon S, Yaqoob P: Conjugated linoleic acid and human health: a critical evaluation of the evidence. Curr Opin Clin Nutr Metab Care. 2006 Mar;9(2):105-10. [PubMed:16477173 ]
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