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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:25 UTC
HMDB IDHMDB0005047
Secondary Accession Numbers
  • HMDB05047
Metabolite Identification
Common Name(9E,11E)-Octadecadienoic acid
DescriptionConjugated 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 ).
Structure
Thumb
Synonyms
Chemical FormulaC18H32O2
Average Molecular Weight280.4455
Monoisotopic Molecular Weight280.240230268
IUPAC Name(9E,11E)-octadeca-9,11-dienoic acid
Traditional Name9E,11E-octadecadienoic acid
CAS Registry Number1839-11-8
SMILES
CCCCCC\C=C\C=C\CCCCCCCC(O)=O
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+
InChI KeyJBYXPOFIGCOSSB-XBLVEGMJSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassLineolic acids and derivatives
Direct ParentLineolic acids and derivatives
Alternative Parents
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
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified19.3 +/- 3.9 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified25.3 +/- 1.1 uMAdult (>18 years old)Both
Lipid peroxidation
details
BloodDetected and Quantified24.0 +/- 11.0 uMAdult (>18 years old)BothPrimary biliary Cirrhosis details
Associated Disorders and Diseases
Disease References
Lipid peroxidation
  1. 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
  1. Braganza JM, Day JP: Serum octadeca-9-11 dienoic acid concentrations in primary biliary cirrhosis. Lancet. 1987 Apr 25;1(8539):987. [PubMed:2882386 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023610
KNApSAcK IDC00053367
Chemspider ID4445923
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5282796
PDB IDNot Available
ChEBI ID88464
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferencePriester, Remmet. 9,11-Octadecadienoic acid. (1939), US 2156737 19390502 CAN 33:44507 AN 1939:44507
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]