Record Information
Version1.0
Creation date2011-09-21 00:32:22 UTC
Update date2019-11-26 03:21:09 UTC
Primary IDFDB023610
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name10E,12Z-Octadecadienoic acid
DescriptionConjugated linoleic acid (CLA) is a collective term for a mixture of positional and geometric isomers of linoleic acid (18:2) in which the two double bonds are conjugated. CLA has been suggested to have effects on human health, including effects on body composition, blood lipids, liver metabolism, insulin sensitivity and immune function, with mixed results. Some reported data suggest that the effects of the substance may be isomer dependent and that cis-9,trans-11 and trans-10,cis-12 conjugated linoleic acids have opposing effects, the later (trans-10,cis-12 CLA) having a relative detrimental effect on blood lipids. (PMID 16477173) [HMDB]
CAS Number2420-56-6
Structure
Thumb
Synonyms
SynonymSource
(9E,11E)-9,11-Octadecadienoic acidChEBI
(e,e)-9,11-Octadecadienoic acidChEBI
(e,e)-Isolinoleic acidChEBI
9-trans, 11-trans-CLAChEBI
9-trans,11-trans-Conjugated linoleic acidChEBI
9-trans,11-trans-Octadecadienoic acidChEBI
9E,11E-CLAChEBI
9t,11t-CLAChEBI
Conjugated (9E,11E)-linoleic acidChEBI
Isolinoleic acidChEBI
Mangold's acidChEBI
trans,trans-9,11-Octadecadienoic acidChEBI
trans-9, trans-11-Octadecadienoic acidChEBI
(9E,11E)-9,11-OctadecadienoateGenerator
(e,e)-9,11-OctadecadienoateGenerator
(e,e)-IsolinoleateGenerator
9-trans,11-trans-Conjugated linoleateGenerator
9-trans,11-trans-OctadecadienoateGenerator
Conjugated (9E,11E)-linoleateGenerator
IsolinoleateGenerator
trans,trans-9,11-OctadecadienoateGenerator
trans-9, trans-11-OctadecadienoateGenerator
(9E,11E)-OctadecadienoateGenerator
9,11-Linoleic acidHMDB, MeSH
CLA 80HMDB
Conjugated linoleic acidHMDB
delta9,11-OctadecadienoateHMDB
Nouracid de 554HMDB
Ricineic acidHMDB
Ricinenic acidHMDB
Selin claHMDB
9,11-Linoleic acid, (E,E)-isomerMeSH, HMDB
9,11-Isolinoleic acidMeSH, HMDB
Octadeca-9,11-dienoic acidMeSH, HMDB
9,11-OctadecadienoateMeSH, HMDB
(9E,11E)-Octadecadienoic acidHMDB
9,11-Conjugated linoleic acidHMDB
9-trans,11-trans-Linoleic acidHMDB
9E,11E-Octadecadienoic acidHMDB
FA(18:2(9E,11E))HMDB
delta9,11-Octadecadienoic acidHMDB
trans-11-trans-9-Octadecadienoic acidHMDB
trans-9,trans-11 Conjugated linoleic acidHMDB
trans-9,trans-11-Octadecadienoic acidHMDB
Δ9,11-Octadecadienoic acidHMDB
9E,11E-OctadecadienoateGenerator
10E,12Z-OctadecadienoateGenerator
(10E,12Z)-10,12-Octadecadienoatehmdb
(10E,12Z)-10,12-Octadecadienoic acidhmdb
10-trans-12-cis-Octadecadienoatehmdb
10-trans-12-cis-Octadecadienoic acidhmdb
10-trans,12-cis-Linoleic acidhmdb
10E,12Z-Octadecadienoic acidhmdb
trans-10-cis-12-Octadecadienoatehmdb
trans-10-cis-12-Octadecadienoic acidhmdb
trans-10,cis-12 Conjugated linoleic acidhmdb
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
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
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-d3517fc9c425686f3f47Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0090000000-dfad2b4819a8e09aeb74Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0093020000-3713e3e16e9fc8ff9d4eSpectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004i-0090000000-1ab95baf25a47f7edbbeSpectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0091000000-88b67552039f5c14c7eaSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-d3517fc9c425686f3f47Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-dfad2b4819a8e09aeb74Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-1ab95baf25a47f7edbbeSpectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-004i-0090000000-d3517fc9c425686f3f47Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-dfad2b4819a8e09aeb74Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-004i-0090000000-1ab95baf25a47f7edbbeSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0090000000-f2c6c9de24118516f0dbSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-022j-5690000000-f4c090f44fe34f660b19Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9830000000-42ee75da80e6ee682b90Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-f1e9e4b543f7d4f48bf8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ti-0090000000-665523c6142ff4e39c96Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9230000000-b43315d97b9995f922a3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01qa-5590000000-6740409ad0ee9d0c387cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05mk-9510000000-78bd3b0ecfca1dab2bacSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0apm-9000000000-98f6af2debd76c0c3c6eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-03fd7d53d39127d02766Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-1090000000-c03baa3d5c1c48e8c45cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9310000000-07f427d77d98dab09f40Spectrum
NMRNot Available
ChemSpider ID4508489
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID5351472
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB05048
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 IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
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