Back to Compounds

Showing Compound 9E,11E-Octadecadienoic acid (FDB023609)

Record Information
Version1.0
Creation date2011-09-21 00:32:22 UTC
Update date2020-09-17 15:33:14 UTC
Primary IDFDB023609
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name9E,11E-Octadecadienoic acid
Description9E,11E-Octadecadienoic acid, also known as (e,e)-isolinoleic acid or (9E,11E)-9,11-octadecadienoate, 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. Conjugated linoleic acid (CLA) 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. 9E,11E-Octadecadienoic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 9E,11E-Octadecadienoic acid has been detected in milk and dairy products (from cow) and red meat. This could make 9E,11E-octadecadienoic acid a potential biomarker for the consumption of these foods. 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 CLA-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, after supplementation with the trans-10, cis-12 conjugated linoleic acid isomer. Diet composition may modulate CLA effects on body fat accumulation. Contemporary dietary recommendations tend to limit red meat and dairy products and the possible CLA deficiencies must be compensated with dietary supplements. However, with human studies, a specific dietary pattern that controls and includes CLA has not been established. As a result, differences among studies and 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 of the participants may also impact these studies (PMID: 17053429, 17217167, 17554969, 16477173).
CAS Number1839-11-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.00015 g/LALOGPS
logP7.11ALOGPS
logP6.42ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)4.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity88.52 m³·mol⁻¹ChemAxon
Polarizability37.12 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC18H32O2
IUPAC name(9E,11E)-octadeca-9,11-dienoic acid
InChI IdentifierInChI=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
Isomeric SMILESCCCCCC\C=C\C=C\CCCCCCCC(O)=O
Average Molecular Weight280.4455
Monoisotopic Molecular Weight280.240230268
Classification
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

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS9E,11E-Octadecadienoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-052f-9550000000-f91f775c11691e572339Spectrum
Predicted GC-MS9E,11E-Octadecadienoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0079-9531000000-ff0f0a6283e777000b03Spectrum
Predicted GC-MS9E,11E-Octadecadienoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0090000000-d3517fc9c425686f3f472017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0090000000-dfad2b4819a8e09aeb742017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0093020000-3713e3e16e9fc8ff9d4e2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004i-0090000000-1ab95baf25a47f7edbbe2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0091000000-88b67552039f5c14c7ea2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-d3517fc9c425686f3f472017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-dfad2b4819a8e09aeb742017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-1ab95baf25a47f7edbbe2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-004i-0090000000-d3517fc9c425686f3f472021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-dfad2b4819a8e09aeb742021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-004i-0090000000-1ab95baf25a47f7edbbe2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0090000000-f2c6c9de24118516f0db2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-022j-5690000000-f4c090f44fe34f660b192017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9830000000-42ee75da80e6ee682b902017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-f1e9e4b543f7d4f48bf82017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ti-0090000000-665523c6142ff4e39c962017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9230000000-b43315d97b9995f922a32017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01qa-5590000000-6740409ad0ee9d0c387c2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05mk-9510000000-78bd3b0ecfca1dab2bac2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0apm-9000000000-98f6af2debd76c0c3c6e2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-03fd7d53d39127d027662021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-1090000000-c03baa3d5c1c48e8c45c2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9310000000-07f427d77d98dab09f402021-09-24View Spectrum
NMRNot Available
ChemSpider ID4445923
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID5282796
Pubchem Substance IDNot Available
ChEBI ID36025
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB05047
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDConjugated linoleic acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference