You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-12-20 20:16:05 UTC
HMDB IDHMDB0000673
Secondary Accession Numbers
  • HMDB00673
Metabolite Identification
Common NameLinoleic acid
DescriptionLinoleic acid is a doubly unsaturated fatty acid, also known as an omega-6 fatty acid, occurring widely in plant glycosides. In this particular polyunsaturated fatty acid (PUFA), the first double bond is located between the sixth and seventh carbon atom from the methyl end of the fatty acid (n-6). Linoleic acid is an essential fatty acid in human nutrition because it cannot be synthesized by humans. It is used in the biosynthesis of prostaglandins (via arachidonic acid) and cell membranes (From Stedman, 26th ed). Linoleic acid is found to be associated with isovaleric acidemia, which is an inborn error of metabolism.
Structure
Thumb
Synonyms
ValueSource
(9Z,12Z)-Octadecadienoic acidChEBI
(Z,Z)-9,12-Octadecadienoic acidChEBI
9-cis,12-cis-Octadecadienoic acidChEBI
9Z,12Z-Octadecadienoic acidChEBI
Acide cis-linoleiqueChEBI
Acide linoleiqueChEBI
acido LinoleicoChEBI
all-cis-9,12-Octadecadienoic acidChEBI
C18:2 9C, 12C Omega6 todos cis-9,12-octadienoicoChEBI
C18:2, N-6,9 all-cisChEBI
cis,cis-9,12-Octadecadienoic acidChEBI
cis,cis-Linoleic acidChEBI
cis-Delta(9,12)-Octadecadienoic acidChEBI
LAChEBI
Linolic acidChEBI
(9Z,12Z)-OctadecadienoateGenerator
LinoleateGenerator
(Z,Z)-9,12-OctadecadienoateGenerator
9-cis,12-cis-OctadecadienoateGenerator
9Z,12Z-OctadecadienoateGenerator
all-cis-9,12-OctadecadienoateGenerator
cis,cis-9,12-OctadecadienoateGenerator
cis,cis-LinoleateGenerator
cis-delta(9,12)-OctadecadienoateGenerator
cis-δ(9,12)-octadecadienoateGenerator
cis-δ(9,12)-octadecadienoic acidGenerator
LinolateGenerator
(9Z,12Z)-9,12-OctadecadienoateHMDB
(9Z,12Z)-9,12-Octadecadienoic acidHMDB
9-cis,12-cis-LinoleateHMDB
9-cis,12-cis-Linoleic acidHMDB
9Z,12Z-LinoleateHMDB
9Z,12Z-Linoleic acidHMDB
cis-9,cis-12-OctadecadienoateHMDB
cis-9,cis-12-Octadecadienoic acidHMDB
cis-D9,12-OctadecadienoateHMDB
cis-D9,12-Octadecadienoic acidHMDB
Emersol 315HMDB
Extra linoleic 90HMDB
Polylin 515HMDB
Unifac 6550HMDB
Acid, 9,12-octadecadienoicMeSH
Linoelaidic acidMeSH
Linoleic acid, (e,e)-isomerMeSH
Linoleic acid, (Z,Z)-isomerMeSH
Linoleic acid, (Z,Z)-isomer, 14C-labeledMeSH
Linoleic acid, ammonium salt, (Z,Z)-isomerMeSH
Linoleic acid, potassium salt, (Z,Z)-isomerMeSH
9 trans,12 trans Octadecadienoic acidMeSH
9-trans,12-trans-Octadecadienoic acidMeSH
Linoleic acid, sodium salt, (e,e)-isomerMeSH
Linoleic acid, sodium salt, (Z,Z)-isomerMeSH
trans,trans-9,12-Octadecadienoic acidMeSH
9,12-Octadecadienoic acidMeSH
Linoelaidic acid, (e,Z)-isomerMeSH
Linoleic acid, calcium salt, (Z,Z)-isomerMeSH
Linolelaidic acidMeSH
9,12 Octadecadienoic acidMeSH
Linoleic acid, (Z,e)-isomerMeSH
Chemical FormulaC18H32O2
Average Molecular Weight280.4455
Monoisotopic Molecular Weight280.240230268
IUPAC Name(9Z,12Z)-octadeca-9,12-dienoic acid
Traditional Namelinoleic
CAS Registry Number60-33-3
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-HZJYTTRNSA-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
Physiological effect

Health effect:

  Health condition:

    Cancer:

    Vascular disorders:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Tissue and substructures:

  Organ and components:

  Cell and elements:

    Cell:

    Element:

Source:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

Role

Industrial application:

Biological role:

Indirect biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-8.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP7.05SANGSTER (1993)
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
Polarizability35.86 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-000t-7900000000-b6ee03c4800464c37471View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-00vi-9300000000-c92dac639ced59eb5dbeView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-003s-9700000000-77e67d7b1a161e6ecfa6View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000t-7900000000-b6ee03c4800464c37471View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00vi-9300000000-c92dac639ced59eb5dbeView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-003s-9700000000-77e67d7b1a161e6ecfa6View in MoNA
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 - Quattro_QQQ 10V, Positive (Annotated)splash10-0f89-0190000000-2be9501b1d4a9fcbd1c0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0uk9-0790000000-7f6e35a591f977bc488eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0udi-0090000000-c56edc2bbf9d6752aec5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - FAB-EBEB (JMS-HX/HX 110A, JEOL) , Negativesplash10-004i-0090000000-baf4579e26c6b393d391View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-004i-0090000000-815c1682b2c59ba96f10View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004i-0090000000-3406b2b2d5756807e1cdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-0090000000-2fb4975278fa4d118f43View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a6r-9380000000-37f833673c248405c8efView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4i-9200000000-7d34ed5900a17ffe3f9bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0090010000-f8df6099e003402f2566View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0091021000-0e44779958d5744d873bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0091021000-0e44779958d5744d873bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0091021000-0e44779958d5744d873bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004i-0091021000-0e44779958d5744d873bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0090010000-f8df6099e003402f2566View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0091021000-0e44779958d5744d873bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0090000000-adbf36f0a17c33ac33f8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0090000000-2747c83af78732eb6e16View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004i-0090000000-a0415b1cb63b4562b40eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0090000000-8bdf8d54a29f73494242View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0239-4590000000-e5ee57553b064eae2efeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00rf-9830000000-b26ba057a2b4d135b478View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-f1e9e4b543f7d4f48bf8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ti-0090000000-665523c6142ff4e39c96View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9240000000-dca36a25ad7519d500c3View in MoNA
MSMass Spectrum (Electron Ionization)splash10-015a-9200000000-a193c27810bedf93c498View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Location
  • Adipose Tissue
  • Erythrocyte
  • Fibroblasts
  • Intestine
  • Kidney
  • Muscle
  • Myelin
  • Placenta
  • Platelet
  • Prostate
  • Skin
  • Spleen
  • Stratum Corneum
Pathways
NameSMPDB/PathwhizKEGG
Alpha Linolenic Acid and Linoleic Acid MetabolismPw000006Pw000006 greyscalePw000006 simpleMap00592
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified23.39 +/- 2.75 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified110 (42-370) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified83.8 +/- 38 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified193.7 +/- 72.0 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified264 +/- 17.0 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified3217.0 +/- 630.1 uMAdult (>18 years old)Not Specified
Normal
details
BloodDetected and Quantified183.7 +/- 69.9 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified207.9 +/- 73.0 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified734.546 +/- 92.710 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified798.729 +/- 99.841 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified927.0964 +/- 110.538 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified930.662 +/- 89.144 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified61 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified17.7 +/- 4.7 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified14.733 +/- 4.331 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified61 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified74 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified134 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified192 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified246 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified291 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified308 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified311 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified525 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified563 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified618 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified1021.482 +/- 224.215 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified1065.519 +/- 201.893 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified3360 +/- 630 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified3250 +/- 600 uMAdult (>18 years old)MaleNormal details
BloodDetected but not Quantified Adult (>18 years old)Both
Normal
details
BloodDetected but not Quantified Adult (>18 years old)Female
Normal
details
BloodDetected and Quantified15.2 +/- 0.437 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified11.0 +/- 3.0 uMAdult (>18 years old)Not SpecifiedNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Infant (0-1 year old)Not Specified
Normal
details
FecesDetected but not Quantified Adult (>18 years old)BothNormal details
FecesDetected but not Quantified Infant (0-1 year old)Not Specified
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)BothNormal details
FecesDetected but not Quantified Children (1-13 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)BothNormal details
FecesDetected but not Quantified Not SpecifiedNot Specified
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Infant (0-1 year old)Both
Normal
details
FecesDetected but not Quantified Not SpecifiedNot Specified
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
details
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified0.05 +/- 0.05 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified1.19 +/- 0.61 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified22.61 +/- 2.80 uMAdult (>18 years old)FemaleGestational diabetes mellitus (GDM) details
BloodDetected and Quantified886.0 +/- 626.6 uMAdult (>18 years old)Both
Cirrhosis
details
BloodDetected but not Quantified Adult (>18 years old)Both
Oesophageal cancer
details
BloodDetected but not Quantified Adult (>18 years old)Both
Lung cancer
details
BloodDetected and Quantified175.9 +/- 65.0 uMAdult (>18 years old)BothHypertension details
BloodDetected and Quantified159 +/- 12.0 uMAdult (>18 years old)Both
Schizophrenia
details
BloodDetected and Quantified2796.7 +/- 493.9 uMAdult (>18 years old)Not Specified
Isovaleric acidemia
details
BloodDetected and Quantified167.0 +/- 63.8 uMAdult (>18 years old)MaleEssential hypertension details
BloodDetected and Quantified195.2 +/- 64.4 uMAdult (>18 years old)FemaleEssential hypertension details
BloodDetected but not Quantified Adult (>18 years old)BothColorectal cancer details
BloodDetected but not Quantified Adult (>18 years old)Both
Schizophrenia
details
BloodDetected but not Quantified Adult (>18 years old)Female
Breast cancer
details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>18 years old)BothICD details
FecesDetected but not Quantified Adult (>18 years old)BothCCD details
FecesDetected but not Quantified Adult (>18 years old)BothCCD details
FecesDetected but not Quantified Adult (>18 years old)BothICD details
FecesDetected but not Quantified Adult (>18 years old)Bothliver cirrhosis details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal cancer details
FecesDetected but not Quantified Adult (>18 years old)FemaleInterstitial cystits details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal cancer details
UrineDetected and Quantified0.18 +/- 0.45 umol/mmol creatinineAdult (>18 years old)FemaleThyroid cancer details
Associated Disorders and Diseases
Disease References
Thyroid cancer
  1. Kim KM, Jung BH, Lho DS, Chung WY, Paeng KJ, Chung BC: Alteration of urinary profiles of endogenous steroids and polyunsaturated fatty acids in thyroid cancer. Cancer Lett. 2003 Dec 30;202(2):173-9. [PubMed:14643447 ]
Cirrhosis
  1. Szebeni J, Eskelson C, Sampliner R, Hartmann B, Griffin J, Dormandy T, Watson RR: Plasma fatty acid pattern including diene-conjugated linoleic acid in ethanol users and patients with ethanol-related liver disease. Alcohol Clin Exp Res. 1986 Dec;10(6):647-50. [PubMed:3101533 ]
Essential hypertension
  1. Wang S, Ma A, Song S, Quan Q, Zhao X, Zheng X: Fasting serum free fatty acid composition, waist/hip ratio and insulin activity in essential hypertensive patients. Hypertens Res. 2008 Apr;31(4):623-32. doi: 10.1291/hypres.31.623. [PubMed:18633173 ]
Schizophrenia
  1. Fukushima T, Iizuka H, Yokota A, Suzuki T, Ohno C, Kono Y, Nishikiori M, Seki A, Ichiba H, Watanabe Y, Hongo S, Utsunomiya M, Nakatani M, Sadamoto K, Yoshio T: Quantitative analyses of schizophrenia-associated metabolites in serum: serum D-lactate levels are negatively correlated with gamma-glutamylcysteine in medicated schizophrenia patients. PLoS One. 2014 Jul 8;9(7):e101652. doi: 10.1371/journal.pone.0101652. eCollection 2014. [PubMed:25004141 ]
  2. Xuan J, Pan G, Qiu Y, Yang L, Su M, Liu Y, Chen J, Feng G, Fang Y, Jia W, Xing Q, He L: Metabolomic profiling to identify potential serum biomarkers for schizophrenia and risperidone action. J Proteome Res. 2011 Dec 2;10(12):5433-43. doi: 10.1021/pr2006796. Epub 2011 Nov 8. [PubMed:22007635 ]
Gestational diabetes
  1. Min Y, Ghebremeskel K, Lowy C, Thomas B, Crawford MA: Adverse effect of obesity on red cell membrane arachidonic and docosahexaenoic acids in gestational diabetes. Diabetologia. 2004 Jan;47(1):75-81. Epub 2003 Nov 22. [PubMed:14634727 ]
Hypertension
  1. Wang S, Ma A, Song S, Quan Q, Zhao X, Zheng X: Fasting serum free fatty acid composition, waist/hip ratio and insulin activity in essential hypertensive patients. Hypertens Res. 2008 Apr;31(4):623-32. doi: 10.1291/hypres.31.623. [PubMed:18633173 ]
Isovaleric acidemia
  1. Dercksen M, Kulik W, Mienie LJ, Reinecke CJ, Wanders RJ, Duran M: Polyunsaturated fatty acid status in treated isovaleric acidemia patients. Eur J Clin Nutr. 2016 Oct;70(10):1123-1126. doi: 10.1038/ejcn.2016.100. Epub 2016 Jun 22. [PubMed:27329611 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012760
KNApSAcK IDC00001224
Chemspider ID4444105
KEGG Compound IDC01595
BioCyc IDLINOLEIC_ACID
BiGG ID37956
Wikipedia LinkLinoleic_acid
METLIN ID191
PubChem Compound5280450
PDB IDEIC
ChEBI ID17351
References
Synthesis ReferenceWalborsky, Harry M.; Davis, Robert H.; Howton, David R. A total synthesis of linoleic acid. Journal of the American Chemical Society (1951), 73 2590-4.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
  2. Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. [PubMed:8412012 ]
  3. Schurer NY, Stremmel W, Grundmann JU, Schliep V, Kleinert H, Bass NM, Williams ML: Evidence for a novel keratinocyte fatty acid uptake mechanism with preference for linoleic acid: comparison of oleic and linoleic acid uptake by cultured human keratinocytes, fibroblasts and a human hepatoma cell line. Biochim Biophys Acta. 1994 Feb 10;1211(1):51-60. [PubMed:8123682 ]
  4. Valianpour F, Wanders RJ, Overmars H, Vaz FM, Barth PG, van Gennip AH: Linoleic acid supplementation of Barth syndrome fibroblasts restores cardiolipin levels: implications for treatment. J Lipid Res. 2003 Mar;44(3):560-6. Epub 2002 Dec 16. [PubMed:12562862 ]
  5. Horrobin DF: Essential fatty acid metabolism and its modification in atopic eczema. Am J Clin Nutr. 2000 Jan;71(1 Suppl):367S-72S. [PubMed:10617999 ]
  6. Imokawa G, Yada Y, Higuchi K, Okuda M, Ohashi Y, Kawamata A: Pseudo-acylceramide with linoleic acid produces selective recovery of diminished cutaneous barrier function in essential fatty acid-deficient rats and has an inhibitory effect on epidermal hyperplasia. J Clin Invest. 1994 Jul;94(1):89-96. [PubMed:8040295 ]
  7. Kawajiri H, Hsi LC, Kamitani H, Ikawa H, Geller M, Ward T, Eling TE, Glasgow WC: Arachidonic and linoleic acid metabolism in mouse intestinal tissue: evidence for novel lipoxygenase activity. Arch Biochem Biophys. 2002 Feb 1;398(1):51-60. [PubMed:11811948 ]
  8. Iso H, Sato S, Umemura U, Kudo M, Koike K, Kitamura A, Imano H, Okamura T, Naito Y, Shimamoto T: Linoleic acid, other fatty acids, and the risk of stroke. Stroke. 2002 Aug;33(8):2086-93. [PubMed:12154268 ]
  9. Seidel D, Heipertz R, Weisner B: Cerebrospinal fluid lipids in demyelinating disease. II. Linoleic acid as an index of impaired blood-CSF barrier. J Neurol. 1980 Jan;222(3):177-82. [PubMed:6153705 ]
  10. Salo P, Seppanen-Laakso T, Laakso I, Seppanen R, Niinikoski H, Viikari J, Simell O: Low-saturated fat, low-cholesterol diet in 3-year-old children: effect on intake and composition of trans fatty acids and other fatty acids in serum phospholipid fraction-The STRIP study. Special Turku coronary Risk factor Intervention Project for children. J Pediatr. 2000 Jan;136(1):46-52. [PubMed:10636973 ]
  11. Grimsgaard S, Bonaa KH, Jacobsen BK, Bjerve KS: Plasma saturated and linoleic fatty acids are independently associated with blood pressure. Hypertension. 1999 Sep;34(3):478-83. [PubMed:10489397 ]

Only showing the first 10 proteins. There are 52 proteins in total.

Enzymes

General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. This isozyme hydrolyzes more efficiently L-alpha-1-palmitoyl-2-oleoyl phosphatidylcholine than L-alpha-1-palmitoyl-2-arachidonyl phosphatidylcholine, L-alpha-1-palmitoyl-2-arachidonyl phosphatidylethanolamine, or L-alpha-1-stearoyl-2-arachidonyl phosphatidylinositol. May be involved in the production of lung surfactant, the remodeling or regulation of cardiac muscle.
Gene Name:
PLA2G5
Uniprot ID:
P39877
Molecular weight:
15674.065
Reactions
Phosphatidylcholine + Water → 1-Acyl-sn-glycero-3-phosphocholine + Linoleic aciddetails
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Hydrolyzes phosphatidylglycerol versus phosphatidylcholine with a 15-fold preference.
Gene Name:
PLA2G2F
Uniprot ID:
Q9BZM2
Molecular weight:
23256.29
Reactions
Phosphatidylcholine + Water → 1-Acyl-sn-glycero-3-phosphocholine + Linoleic aciddetails
General function:
Involved in metabolic process
Specific function:
Selectively hydrolyzes arachidonyl phospholipids in the sn-2 position releasing arachidonic acid. Together with its lysophospholipid activity, it is implicated in the initiation of the inflammatory response.
Gene Name:
PLA2G4A
Uniprot ID:
P47712
Molecular weight:
85210.19
Reactions
Phosphatidylcholine + Water → 1-Acyl-sn-glycero-3-phosphocholine + Linoleic aciddetails
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides.
Gene Name:
PLA2G1B
Uniprot ID:
P04054
Molecular weight:
16359.535
Reactions
Phosphatidylcholine + Water → 1-Acyl-sn-glycero-3-phosphocholine + Linoleic aciddetails
General function:
Involved in phospholipase A2 activity
Specific function:
Not known; does not seem to have catalytic activity.
Gene Name:
PLA2G12B
Uniprot ID:
Q9BX93
Molecular weight:
Not Available
Reactions
Phosphatidylcholine + Water → 1-Acyl-sn-glycero-3-phosphocholine + Linoleic aciddetails
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a powerful potency for releasing arachidonic acid from cell membrane phospholipids. Prefers phosphatidylethanolamine and phosphatidylcholine liposomes to those of phosphatidylserine.
Gene Name:
PLA2G10
Uniprot ID:
O15496
Molecular weight:
18153.04
Reactions
Phosphatidylcholine + Water → 1-Acyl-sn-glycero-3-phosphocholine + Linoleic aciddetails
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a preference for arachidonic-containing phospholipids.
Gene Name:
PLA2G2E
Uniprot ID:
Q9NZK7
Molecular weight:
15988.525
Reactions
Phosphatidylcholine + Water → 1-Acyl-sn-glycero-3-phosphocholine + Linoleic aciddetails
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Does not exhibit detectable activity toward sn-2-arachidonoyl- or linoleoyl-phosphatidylcholine or -phosphatidylethanolamine.
Gene Name:
PLA2G12A
Uniprot ID:
Q9BZM1
Molecular weight:
21066.99
Reactions
Phosphatidylcholine + Water → 1-Acyl-sn-glycero-3-phosphocholine + Linoleic aciddetails
General function:
Involved in metabolic process
Specific function:
Catalyzes the release of fatty acids from phospholipids. It has been implicated in normal phospholipid remodeling, nitric oxide-induced or vasopressin-induced arachidonic acid release and in leukotriene and prostaglandin production. May participate in fas mediated apoptosis and in regulating transmembrane ion flux in glucose-stimulated B-cells. Has a role in cardiolipin (CL) deacylation. Required for both speed and directionality of monocyte MCP1/CCL2-induced chemotaxis through regulation of F-actin polymerization at the pseudopods. Isoform ankyrin-iPLA2-1 and isoform ankyrin-iPLA2-2, which lack the catalytic domain, are probably involved in the negative regulation of iPLA2 activity.
Gene Name:
PLA2G6
Uniprot ID:
O60733
Molecular weight:
84092.635
Reactions
Phosphatidylcholine + Water → 1-Acyl-sn-glycero-3-phosphocholine + Linoleic aciddetails
General function:
Involved in phospholipase A2 activity
Specific function:
Thought to participate in the regulation of the phospholipid metabolism in biomembranes including eicosanoid biosynthesis. Catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides.
Gene Name:
PLA2G2A
Uniprot ID:
P14555
Molecular weight:
16082.525
Reactions
Phosphatidylcholine + Water → 1-Acyl-sn-glycero-3-phosphocholine + Linoleic aciddetails

Only showing the first 10 proteins. There are 52 proteins in total.