Record Information
Version1.0
Creation Date2016-09-30 23:21:03 UTC
Update Date2020-06-04 22:43:33 UTC
BMDB IDBMDB0006270
Secondary Accession Numbers
  • BMDB06270
Metabolite Identification
Common NameLinoelaidic acid
DescriptionLinoleic acid, also known as linoleate, 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. Linoleic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Linoleic acid exists in all eukaryotes, ranging from yeast to humans.
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
9E,12E-OctadecadienoateGenerator
trans-9,trans-12-LinoleateGenerator
LinoelaidateGenerator
(9E,12E)-9,12-OctadecadienoateHMDB
(9E,12E)-9,12-Octadecadienoic acidHMDB
9,12-Octadecadienoic acidMeSH, HMDB
Linoleic acidMeSH, HMDB
Linoleic acid, (Z,Z)-isomer, 14C-labeledMeSH, HMDB
Linolelaidic acidMeSH, HMDB
cis,cis-9,12-Octadecadienoic acidMeSH, HMDB
Linoleic acid, (e,e)-isomerMeSH, HMDB
Linoleic acid, (Z,Z)-isomerMeSH, HMDB
Linoleic acid, ammonium salt, (Z,Z)-isomerMeSH, HMDB
Linoleic acid, potassium salt, (Z,Z)-isomerMeSH, HMDB
Linoelaidic acid, (e,Z)-isomerMeSH, HMDB
9 trans,12 trans Octadecadienoic acidMeSH, HMDB
Linoleic acid, sodium salt, (e,e)-isomerMeSH, HMDB
Linoleic acid, sodium salt, (Z,Z)-isomerMeSH, HMDB
Acid, 9,12-octadecadienoicMeSH, HMDB
trans,trans-9,12-Octadecadienoic acidMeSH, HMDB
Linoleic acid, (Z,e)-isomerMeSH, HMDB
9,12 Octadecadienoic acidMeSH, HMDB
Linoleic acid, calcium salt, (Z,Z)-isomerMeSH, HMDB
9-trans,12-trans-Octadecadienoic acidMeSH, HMDB
LinoleateMeSH, HMDB, Generator
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
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
StatusDetected and Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
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
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
Polarizability35.45 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
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
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-004i-0090000000-fdabfebc98e900a3a52bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-dd6cf3859995c0ba8be8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-004i-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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-03fd7d53d39127d02766View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-1090000000-e5b6404e73269d5a2528View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9210000000-da81d6d1d7b1e626e905View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Adipose Tissue
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Adipose TissueDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Adipose TissueDetected and Quantified5522.11 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • C. Mapiye, T.D.Tu...
details
Adipose TissueDetected and Quantified5275.89 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • C. Mapiye, T.D.Tu...
details
Adipose TissueDetected and Quantified38145.42 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • C. Mapiye, T.D.Tu...
details
Adipose TissueDetected and Quantified47861.6 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • C. Mapiye, T.D.Tu...
details
Adipose TissueDetected and Quantified37266.63 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • C. Mapiye, T.D.Tu...
details
Adipose TissueDetected and Quantified44394.79 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • C. Mapiye, T.D.Tu...
details
Adipose TissueDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Adipose TissueDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Adipose TissueDetected and Quantified42361.17 nmol/g of tissueNot SpecifiedNot Specified
Normal
details
Adipose TissueDetected and Quantified46533.11 nmol/g of tissueNot SpecifiedNot Specified
Normal
details
Adipose TissueDetected and Quantified40678.14 nmol/g of tissueNot SpecifiedNot Specified
Normal
details
Adipose TissueDetected and Quantified45099.67 nmol/g of tissueNot SpecifiedNot Specified
Normal
details
Adipose TissueDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Adipose TissueDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Adipose TissueDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Adipose TissueDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Adipose TissueDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0006270
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023868
KNApSAcK IDC00036669
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)Not Available
General References
  1. Trimigno A, Munger L, Picone G, Freiburghaus C, Pimentel G, Vionnet N, Pralong F, Capozzi F, Badertscher R, Vergeres G: GC-MS Based Metabolomics and NMR Spectroscopy Investigation of Food Intake Biomarkers for Milk and Cheese in Serum of Healthy Humans. Metabolites. 2018 Mar 23;8(2). pii: metabo8020026. doi: 10.3390/metabo8020026. [PubMed:29570652 ]