9E,11E-Octadecadienoic acid (CHEM035845)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 06:42:59 UTC
Update Date2016-11-09 01:21:23 UTC
Accession NumberCHEM035845
Identification
Common Name9E,11E-Octadecadienoic acid
ClassSmall Molecule
DescriptionAn octadeca-9,11-dienoic acid having 9-cis,11-trans-stereochemistry.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(9Z,11E)-Octadecadienoic acidChEBI
(Z,e)-Octadeca-9,11-dienoic acidChEBI
9(Z),11(e)-Octadecadienoic acidChEBI
9,11-cis,trans-Octadecanoic acidChEBI
9-cis-11-trans-Linoleic acidChEBI
C18:2, N-7,9 trans,cisChEBI
cis-9,trans-11 Conjugated linoleic acidChEBI
cis-9,trans-11-CLAChEBI
Rumenic acidChEBI
9-cis,11-trans-OctadecadienoateKegg
(9Z,11E)-OctadecadienoateGenerator
(Z,e)-Octadeca-9,11-dienoateGenerator
9(Z),11(e)-OctadecadienoateGenerator
9,11-cis,trans-OctadecanoateGenerator
9-cis-11-trans-LinoleateGenerator
cis-9,trans-11 Conjugated linoleateGenerator
RumenateGenerator
9-cis,11-trans-Octadecadienoic acidGenerator
BovinateGenerator
(9Z,11E)-Conjugated linoleic acidHMDB
(9Z,11E)-Octadeca-9,11-dienoateHMDB
(9Z,11E)-Octadeca-9,11-dienoic acidHMDB
9-cis,11-trans-Octadecadienoic acid solutionHMDB
9Z,11E-CLAHMDB
9Z,11E-OctadecadienoateHMDB
9Z,11E-Octadecadienoic acidHMDB
cis-9, trans-11-OctadecadienoateHMDB
cis-9, trans-11-Octadecadienoic acidHMDB
Conjugated (9Z,11E)-linoleic acid solutionHMDB
(9Z,11E)-9,11-Octadecadienoic acidHMDB
9,11-Linoleic acidHMDB
9,11-Linoleic acid, (Z,e)-isomerHMDB
cis-9-trans-11-Octadecadienoic acidHMDB
9,11-Isolinoleic acidHMDB
9,11-Octadecadienoic acidHMDB
9-cis-11-trans-Octadecadienoic acidHMDB
Octadeca-9,11-dienoic acidHMDB
9,11-OctadecadienoateHMDB
c9t11 CLAHMDB
9-cis,11-trans-Linoleic acidHMDB
FA(18:2(9Z,11E))HMDB
cis-9,trans-11-Octadecadienoic acidHMDB
trans-11-cis-9-Octadecadienoic acidHMDB
Bovinic acidHMDB
Chemical FormulaC18H32O2
Average Molecular Mass280.446 g/mol
Monoisotopic Mass280.240 g/mol
CAS Registry Number1839-11-8
IUPAC Name(9Z,11E)-octadeca-9,11-dienoic acid
Traditional Namecis-9,trans-11-CLA
SMILESCCCCCC\C=C\C=C\CCCCCCCC(O)=O
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
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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
Polarizability36.55 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9550000000-f91f775c11691e572339Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0079-9531000000-ff0f0a6283e777000b03Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0090000000-e92f42e010cf8de7d842Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004i-0090000000-b39dc5a43bb0b5730a2fSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0090000000-5eb9e4ae49ad1fb539cdSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0091010000-52cb4af6370469644ffaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-e92f42e010cf8de7d842Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-b39dc5a43bb0b5730a2fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-5eb9e4ae49ad1fb539cdSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-e92f42e010cf8de7d842Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-004i-0090000000-5eb9e4ae49ad1fb539cdSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-004i-0090000000-b39dc5a43bb0b5730a2fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-f1e9e4b543f7d4f48bf8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ti-0090000000-665523c6142ff4e39c96Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9230000000-b43315d97b9995f922a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-03fd7d53d39127d02766Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-1090000000-c03baa3d5c1c48e8c45cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9310000000-07f427d77d98dab09f40Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0090000000-f2c6c9de24118516f0dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-022j-5690000000-f4c090f44fe34f660b19Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9830000000-42ee75da80e6ee682b90Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01qa-5590000000-6740409ad0ee9d0c387cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05mk-9510000000-78bd3b0ecfca1dab2bacSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0apm-9000000000-98f6af2debd76c0c3c6eSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0003797
FooDB IDFDB093753
Phenol Explorer IDNot Available
KNApSAcK IDC00052217
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkRumenic acid
Chemspider ID4444245
ChEBI ID32798
PubChem Compound ID5280644
Kegg Compound IDC04056
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15829653
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=16303327
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=16890934
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=18567757
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=19083449
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=9727617
7. Soyeurt H, Dardenne P, Dehareng F, Lognay G, Veselko D, Marlier M, Bertozzi C, Mayeres P, Gengler N: Estimating fatty acid content in cow milk using mid-infrared spectrometry. J Dairy Sci. 2006 Sep;89(9):3690-5. doi: 10.3168/jds.S0022-0302(06)72409-2.
8. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.
9. van Gastelen S, Antunes-Fernandes EC, Hettinga KA, Dijkstra J: Relationships between methane emission of Holstein Friesian dairy cows and fatty acids, volatile metabolites and non-volatile metabolites in milk. Animal. 2017 Sep;11(9):1539-1548. doi: 10.1017/S1751731117000295. Epub 2017 Feb 21.
10. M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189
11. Jiang J, Wolk A, Vessby B: Relation between the intake of milk fat and the occurrence of conjugated linoleic acid in human adipose tissue. Am J Clin Nutr. 1999 Jul;70(1):21-7.
12. Lock AL, Bauman DE: Modifying milk fat composition of dairy cows to enhance fatty acids beneficial to human health. Lipids. 2004 Dec;39(12):1197-206.