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Record Information
Version1.0
Creation Date2016-09-30 22:34:43 UTC
Update Date2020-06-04 22:31:33 UTC
BMDB IDBMDB0000673
Secondary Accession Numbers
  • BMDB00673
Metabolite Identification
Common NameLinoleic acid
DescriptionLinoleic acid, also known as LA or 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 liquid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Linoleic acid exists in all living organisms, ranging from bacteria to humans. Linoleic acid is a potentially toxic compound. Linoleic acid has been found to be associated with several diseases known as hypertension, ulcerative colitis, essential hypertension, and thyroid cancer; also linoleic acid has been linked to the inborn metabolic disorders including isovaleric acidemia.
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
9-cis,12-cis-OctadecadienoateKegg
(9Z,12Z)-OctadecadienoateGenerator
(Z,Z)-9,12-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
LinoleateGenerator
(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-octadecadienoicHMDB
Linoelaidic acidHMDB
Linoleic acid, (e,e)-isomerHMDB
Linoleic acid, (Z,Z)-isomerHMDB
Linoleic acid, (Z,Z)-isomer, 14C-labeledHMDB
Linoleic acid, ammonium salt, (Z,Z)-isomerHMDB
Linoleic acid, potassium salt, (Z,Z)-isomerHMDB
9 trans,12 trans Octadecadienoic acidHMDB
9-trans,12-trans-Octadecadienoic acidHMDB
Linoleic acid, sodium salt, (e,e)-isomerHMDB
Linoleic acid, sodium salt, (Z,Z)-isomerHMDB
trans,trans-9,12-Octadecadienoic acidHMDB
9,12-Octadecadienoic acidHMDB
Linoelaidic acid, (e,Z)-isomerHMDB
Linoleic acid, calcium salt, (Z,Z)-isomerHMDB
Linolelaidic acidHMDB
9,12 Octadecadienoic acidHMDB
Linoleic acid, (Z,e)-isomerHMDB
FA(18:2(9Z,12Z))HMDB
Chemical FormulaC18H32O2
Average Molecular Weight280.4455
Monoisotopic Molecular Weight280.240230268
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number60-33-3
SMILESNot Available
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
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
  • Myelin sheath
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-8.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP7.05SANGSTER (1993)
Predicted PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
  • Myelin sheath
Biospecimen Locations
  • Adipose Tissue
  • Blood
  • Epidermis
  • Erythrocyte
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Mammary Gland
  • Milk
  • Muscle
  • Neuron
  • Oocyte
  • Placenta
  • Platelet
  • Prostate Tissue
  • Ruminal Fluid
  • Spleen
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Adipose TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
ErythrocyteExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
IntestineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified7.04 +/- 0.14 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified14 +/- 1 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified14 +/- 1 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified12.4 +/- 0.3 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified10.56 +/- 1.06 uMNot SpecifiedNot Specified
Normal
    • Bashar Amer, Caro...
details
MilkDetected and Quantified10.03 +/- 1.06 uMNot SpecifiedNot Specified
Normal
    • Bashar Amer, Caro...
details
MilkDetected and Quantified3.17 +/- 0.53 uMNot SpecifiedNot Specified
Normal
    • Bashar Amer, Caro...
details
MilkDetected and Quantified213.945 uMNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified178.288 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified9.49 +/- 0.08 uMNot SpecifiedNot Specified
Normal
    • Bashar Amer, Caro...
details
MilkDetected and Quantified213.945 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified2567.344 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified3779.701 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified3779.701 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified3209.185 +/- 1069.728 uMNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • Kurt J. Boudonck,...
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • Kurt J. Boudonck,...
details
MilkDetected and Quantified1854.196 +/- 392.234 uMNot SpecifiedNot Specified
Normal
    • M. Ferrand et al....
details
MilkDetected and Quantified2816.952 +/- 677.495 uMNot SpecifiedNot Specified
Normal
    • M. Ferrand et al....
details
MilkDetected and Quantified1747.223 +/- 356.576 uMNot SpecifiedNot Specified
Normal
    • M. Ferrand et al....
details
MilkDetected and Quantified2674.321 +/- 570.522 uMNot SpecifiedNot Specified
Normal
    • M. Ferrand et al....
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • Lawrence K. Cream...
details
MilkDetected and Quantified21394.531 uMNot SpecifiedNot SpecifiedNormal
    • M.J. Abarghuei, Y...
details
MilkDetected and Quantified26386.588 uMNot SpecifiedNot SpecifiedNormal
    • M.J. Abarghuei, Y...
details
MilkDetected and Quantified27456.315 uMNot SpecifiedNot SpecifiedNormal
    • M.J. Abarghuei, Y...
details
MilkDetected and Quantified28882.617 uMNot SpecifiedNot SpecifiedNormal
    • M.J. Abarghuei, Y...
details
MuscleDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
OocyteDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlateletExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Ruminal FluidDetected and Quantified3.5 +/- 2.6 uMNot SpecifiedNot SpecifiedNormal
    • Fozia Saleem, Sou...
details
SpleenExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Heat stress
details
HMDB IDHMDB0000673
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB006287
KNApSAcK IDC00001224
Chemspider ID4444105
KEGG Compound IDC01595
BioCyc IDLINOLEIC_ACID
BiGG ID37956
Wikipedia LinkLinoleic_acid
METLIN ID191
PubChem Compound5280450
PDB IDNot Available
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)Not Available
General References
  1. 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. [PubMed:16899705 ]
  2. Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. [PubMed:11913692 ]
  3. Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11. [PubMed:9718493 ]
  4. Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3. [PubMed:1779072 ]
  5. Colman E, Fokkink WB, Craninx M, Newbold JR, De Baets B, Fievez V: Effect of induction of subacute ruminal acidosis on milk fat profile and rumen parameters. J Dairy Sci. 2010 Oct;93(10):4759-73. doi: 10.3168/jds.2010-3158. [PubMed:20855010 ]
  6. Keenan TW, Morre DJ, Olson DE, Yunghans WN, Patton S: Biochemical and morphological comparison of plasma membrane and milk fat globule membrane from bovine mammary gland. J Cell Biol. 1970 Jan;44(1):80-93. [PubMed:5409465 ]
  7. 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. [PubMed:28219465 ]
  8. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
  9. M. Ferrand, B. Huquet. S. Barbey, F. Barillet, F. Faucon, H. Larroque, O. Leray, J.M. Trommenschlager, M. Brochard (2011). 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. Chemometrics and Intelligent Laboratory Systems.
  10. Lawrence K. Creamer, Alastair K.H. MacGibbon (1996). Lawrence K. Creamer, Alastair K.H. MacGibbon. Some recent advances in the basic chemistry of milk proteins and lipids. International Dairy J. (1996) 6(6):539-568 doi: 10.1016/0958-6946(96)85309-X. International Dairy Journal.
  11. M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri (2014). M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80 doi: 10.1016/j.livsci.2014.03.021. Livestock Science.
  12. Fooddata+, The Technical University of Denmark (DTU) [Link]

Enzymes

General function:
Lipid transport and metabolism
Specific function:
Acts as a fatty acyl-coenzyme A (CoA) desaturase that introduces a cis double bond at carbon 6 of the fatty acyl chain. Involved in biosynthesis of highly unsaturated fatty acids (HUFA) from the essential polyunsaturated fatty acids (PUFA) linoleic acid (LA) (18:2n-6) and alpha-linolenic acid (ALA) (18:3n-3) precursors. Catalyzes the first and rate limiting step in this pathway which is the desaturation of LA (18:2n-6) and ALA (18:3n-3) into gamma-linoleate (GLA) (18:3n-6) and stearidonate (18:4n-3), respectively (By similarity). Subsequently, in the biosynthetic pathway of HUFA n-3 series, desaturates tetracosapentaenoate (24:5n-3) to tetracosahexaenoate (24:6n-3), which is then converted to docosahexaenoate (DHA)(22:6n-3), an important lipid for nervous system function (By similarity). Desaturates palmitate to produce the mono-unsaturated fatty acid sapienate, the most abundant fatty acid in sebum (By similarity). Also desaturates (11E)-octadecenoate (trans-vaccenoate)(18:1n-9), a metabolite in the biohydrogenation pathway of LA (18:2n-6) (By similarity).
Gene Name:
FADS2
Uniprot ID:
A4FV48
Molecular weight:
52533.0
Reactions
Linoleic acid → Gamma-Linolenic aciddetails