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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2007-05-22 20:46:11 UTC
Update Date2018-05-20 02:33:43 UTC
HMDB IDHMDB0006270
Secondary Accession Numbers
  • HMDB06270
Metabolite Identification
Common NameLinoelaidic acid
DescriptionLinoelaidic acid is an isomer of linoleic acid, or conjugated linoleic acid (CLA), a derivative of a fatty acid linoleic acid. Conjugated linoleic acid (CLA) isomers, a group of positional and geometric isomers of linoleic acid [18:2(n-6)], have been studied extensively due to their ability to modulate cancer, atherosclerosis, obesity, immune function and diabetes in a variety of experimental models. CLA's ability to modulate human obesity remains controversial because data from clinical trials using mixed isomers are conflicting. (PMID 10759137 ). Trans fatty acids are characteristically produced during industrial hydrogenation of plant oils.
Structure
Thumb
Synonyms
ValueSource
18:2, N-6,9 all-transChEBI
9E,12E-Octadecadienoic acidChEBI
C18:2, N-6,9 all-transChEBI
trans-9,trans-12-Linoleic acidChEBI
LinoelaidateGenerator
9E,12E-OctadecadienoateGenerator
trans-9,trans-12-LinoleateGenerator
(9E,12E)-9,12-OctadecadienoateHMDB
(9E,12E)-9,12-Octadecadienoic acidHMDB
9,12-Octadecadienoic acidMeSH
Linoleic acidMeSH
Linoleic acid, (Z,Z)-isomer, 14C-labeledMeSH
Linolelaidic acidMeSH
cis,cis-9,12-Octadecadienoic acidMeSH
Linoleic acid, (e,e)-isomerMeSH
Linoleic acid, (Z,Z)-isomerMeSH
Linoleic acid, ammonium salt, (Z,Z)-isomerMeSH
Linoleic acid, potassium salt, (Z,Z)-isomerMeSH
Linoelaidic acid, (e,Z)-isomerMeSH
9 trans,12 trans Octadecadienoic acidMeSH
Linoleic acid, sodium salt, (e,e)-isomerMeSH
Linoleic acid, sodium salt, (Z,Z)-isomerMeSH
Acid, 9,12-octadecadienoicMeSH
trans,trans-9,12-Octadecadienoic acidMeSH
Linoleic acid, (Z,e)-isomerMeSH
9,12 Octadecadienoic acidMeSH
Linoleic acid, calcium salt, (Z,Z)-isomerMeSH
9-trans,12-trans-Octadecadienoic acidMeSH
LinoleateMeSH
Chemical FormulaC18H32O2
Average Molecular Weight280.4455
Monoisotopic Molecular Weight280.240230268
IUPAC Name(9E,12E)-octadeca-9,12-dienoic acid
Traditional Namelinoelaidic acid
CAS Registry Number506-21-8
SMILES
CCCCC\C=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/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6+,10-9+
InChI KeyOYHQOLUKZRVURQ-AVQMFFATSA-N
Chemical Taxonomy
DescriptionThis compound 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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point28 - 29 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00015 g/LALOGPS
logP7.06ALOGPS
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
Polarizability36.8 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0007-9750000000-50d69948d56dd2ba6e42View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0079-9631000000-cc93c24bbf14d81ae9b6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0udi-0009000000-4dd23c77f8e48c0ab9ecView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0udi-0009000000-4dd23c77f8e48c0ab9ecView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0092000000-b8aabbdc61f9b89ac359View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0092000000-b8aabbdc61f9b89ac359View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004i-0092000000-b8aabbdc61f9b89ac359View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0090000000-dd6cf3859995c0ba8be8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0090000000-fdabfebc98e900a3a52bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0092000000-b8aabbdc61f9b89ac359View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0091000000-d8e32f26b102cfd39457View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004i-0090000000-e1aa5a6fc5d53c0d0cb6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-dd6cf3859995c0ba8be8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-fdabfebc98e900a3a52bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-e1aa5a6fc5d53c0d0cb6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0190000000-76fe39ad6bbee3f769e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0239-5690000000-9af1d7ecbc9ccf182d61View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-8930000000-0032f23abecb3b362ff2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-b26f2ec0d32875acf897View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004r-1090000000-08e28514e79444592bb5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9230000000-d3f27ea65196f222f6cdView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Infant (0-1 year old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not Quantified Adult (>18 years old)Both
Lung cancer
details
Associated Disorders and Diseases
Disease References
Lung Cancer
  1. Chen Y, Ma Z, Min L, Li H, Wang B, Zhong J, Dai L: Biomarker identification and pathway analysis by serum metabolomics of lung cancer. Biomed Res Int. 2015;2015:183624. doi: 10.1155/2015/183624. Epub 2015 Apr 16. [PubMed:25961003 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023868
KNApSAcK IDNot Available
Chemspider ID4445609
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG ID2217974
Wikipedia LinkLinoelaidic_acid
METLIN IDNot Available
PubChem Compound5282457
PDB IDNot Available
ChEBI ID75108
References
Synthesis ReferenceGunstone, Frank D.; Lie Ken Jie, M. Fatty acids. 24. Synthesis of ten octadecadiynoic acids and of the related cis,cis- and trans,trans-octadecadienoic acids. Chemistry and Physics of Lipids (1970), 4(1), 1-14.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. MacDonald HB: Conjugated linoleic acid and disease prevention: a review of current knowledge. J Am Coll Nutr. 2000 Apr;19(2 Suppl):111S-118S. [PubMed:10759137 ]