CHEBI:17351 - linoleic acid

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ChEBI Name linoleic acid
ChEBI ID CHEBI:17351
Definition An octadecadienoic acid in which the two double bonds are at positions 9 and 12 and have Z (cis) stereochemistry.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:42395, CHEBI:6479, CHEBI:25047
Supplier Information eMolecules:537269, ZINC000004543724
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Wikipedia License
Docosatetraenoic acid designates any straight chain 22:4 fatty acid. (See Essential fatty acid for nomenclature.) One isomer is of particular interest: all-cis-7,10,13,16-docosatetraenoic acid is an ω-6 fatty acid with the common name adrenic acid (AdA). This is a naturally occurring polyunsaturated fatty acid formed through a 2-carbon chain elongation of arachidonic acid. It is one of the most abundant fatty acids in the early human brain. This unsaturated fatty acid is also metabolized by cells to biologically active products viz., dihomoprostaglandins, and epoxydocosatrienoic acids (EDTs, also known as dihomo-EETs). In addition to being endothelium-derived hyperpolarizing factors, EDTs have demonstrated anti-endoplasmic reticulum stress and anti-nociceptive activities. They are hydrolyzed by the soluble epoxide hydrolase (sEH) to dihydroxydocosatrienoic acids (DHDTs) and hence might play a role in the efficacy of sEH inhibitors.
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Formula C18H32O2
Net Charge 0
Average Mass 280.44550
Monoisotopic Mass 280.24023
InChI 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-
InChIKey OYHQOLUKZRVURQ-HZJYTTRNSA-N
SMILES CCCCC\C=C/C\C=C/CCCCCCCC(O)=O
Metabolite of Species Details
Carthamus oxyacantha (NCBI:txid122010) Found in aerial part (BTO:0001658). Crude ethanolic extract of aerial parts See: PubMed
Daphnia galeata (NCBI:txid27404) See: Is the fatty acid composition of Daphnia galeata determined by the fatty acid composition of the ingested diet?Weers P.M.M., Siewertsen K., and Gulati R.D.Freshwater Biology (1997), 38, 731-738
Chlamydomonas reinhardtii (NCBI:txid3055) See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): algal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in algae including unicellular organisms like chlorella and diatoms to multicellular organisms like giant kelps and brown algae.
Daphnia galeata metabolite
A Daphnia metabolite produced by the species Daphnia galeata.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing linoleic acid (CHEBI:17351) has role Daphnia galeata metabolite (CHEBI:83038)
linoleic acid (CHEBI:17351) has role algal metabolite (CHEBI:84735)
linoleic acid (CHEBI:17351) has role plant metabolite (CHEBI:76924)
linoleic acid (CHEBI:17351) is a ω−6 fatty acid (CHEBI:36009)
linoleic acid (CHEBI:17351) is a octadecadienoic acid (CHEBI:25627)
linoleic acid (CHEBI:17351) is conjugate acid of linoleate (CHEBI:30245)
Incoming (11S)-11-hydroperoxylinoleic acid (CHEBI:15657) has functional parent linoleic acid (CHEBI:17351)
(24S)-24-hydroxycholesterol 3-linoleoate (CHEBI:82875) has functional parent linoleic acid (CHEBI:17351)
(9S),10-epoxy-(10,12Z)-octadecadienoic acid (CHEBI:143790) has functional parent linoleic acid (CHEBI:17351)
(9Z,12Z)-11-hydroxyoctadecadienoic acid (CHEBI:137305) has functional parent linoleic acid (CHEBI:17351)
1,1ʼ,2-trilinoleoyl-2ʼ-oleoyl cardiolipin (CHEBI:84399) has functional parent linoleic acid (CHEBI:17351)
1,1ʼ,2-trilinoleoyl-2ʼ-palmitoyl cardiolipin (CHEBI:84400) has functional parent linoleic acid (CHEBI:17351)
1,1'-dilinoleoyl-2-oleoyl monolysocardiolipin (CHEBI:84583) has functional parent linoleic acid (CHEBI:17351)
1,2,2ʼ-trilinoleoyl-,1ʼ-monolysocardiolipin (CHEBI:84581) has functional parent linoleic acid (CHEBI:17351)
1,2,3-trilinoleoylglycerol (CHEBI:75844) has functional parent linoleic acid (CHEBI:17351)
1,2-di-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphoethanolamine (CHEBI:84846) has functional parent linoleic acid (CHEBI:17351)
1,2-di-[(9Z,12Z)-octadecadienoyl]-sn-glycero-3-phosphocholine (CHEBI:42027) has functional parent linoleic acid (CHEBI:17351)
1,2-dilinoleoyl-3-[α-D-galactosyl-(1→6)-β-D-galactosyl]-sn-glycerol (CHEBI:136796) has functional parent linoleic acid (CHEBI:17351)
1,2-dilinoleoyl-sn-glycero-3-phospho-1D-myo-inositol (CHEBI:77348) has functional parent linoleic acid (CHEBI:17351)
1,2-dilinoleoyl-sn-glycero-3-phospho-1D-myo-inositol 5-phosphate (CHEBI:77349) has functional parent linoleic acid (CHEBI:17351)
1,2-dilinoleoyl-sn-glycerol (CHEBI:77127) has functional parent linoleic acid (CHEBI:17351)
1,2-dioleoyl-3-linoleoyl-sn-glycerol (CHEBI:77683) has functional parent linoleic acid (CHEBI:17351)
1,3-dilinoleoylglycerol (CHEBI:75850) has functional parent linoleic acid (CHEBI:17351)
1-(1Z,11Z-octadecadienyl)-2-linoleoyl-sn-glycero-3-phosphoethanolamine (CHEBI:90486) has functional parent linoleic acid (CHEBI:17351)
1-(1Z-hexadecenyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine (CHEBI:84557) has functional parent linoleic acid (CHEBI:17351)
1-(1Z-hexadecenyl)-2-linoleoyl-sn-glycero-3-phosphoethanolamine (CHEBI:84532) has functional parent linoleic acid (CHEBI:17351)
1-(1Z-octadecenyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine (CHEBI:84555) has functional parent linoleic acid (CHEBI:17351)
1-(1Z-octadecenyl)-2-linoleoyl-sn-glycero-3-phosphoethanolamine (CHEBI:90483) has functional parent linoleic acid (CHEBI:17351)
1-O-linoleoyl-N-acetylsphingosine (CHEBI:76086) has functional parent linoleic acid (CHEBI:17351)
1-[(10Z,13Z,16Z)-docosatrienoyl]-2-linoleoyl-sn-glycero-3-phospho-1D-myo-inositol (CHEBI:89249) has functional parent linoleic acid (CHEBI:17351)
1-[(13Z,16Z)-docosadienoyl]-2-linoleoyl-sn-glycero-3-phospho-1D-myo-inositol (CHEBI:89245) has functional parent linoleic acid (CHEBI:17351)
1-[(5Z,8Z,11Z,14Z)-eicosatetraenoyl]-2-[(9Z,12Z)-octadecadienoyl]-sn-glycero-3-phosphocholine (CHEBI:86184) has functional parent linoleic acid (CHEBI:17351)
1-[(9Z,12Z)-octadecadienoyl]-2-[(5Z,8Z,11Z,14Z)-icosatetraenoyl]-sn-glycero-3-phosphocholine (CHEBI:84563) has functional parent linoleic acid (CHEBI:17351)
1-[(9Z,12Z)-octadecadienoyl]-2-hexadecanoyl-sn-glycero-3-phosphocholine (CHEBI:86099) has functional parent linoleic acid (CHEBI:17351)
1-[(9Z,12Z)-octadecadienoyl]-2-icosanoyl-sn-glycerol (CHEBI:86985) has functional parent linoleic acid (CHEBI:17351)
1-[(9Z,12Z)-octadecadienoyl]-2-octadecanoyl-sn-glycero-3-phosphocholine (CHEBI:86112) has functional parent linoleic acid (CHEBI:17351)
1-[(9Z,12Z)-octadecadienoyl]-2-octadecanoyl-sn-glycerol (CHEBI:86337) has functional parent linoleic acid (CHEBI:17351)
1-acyl-2-linoleoyl-sn-glycero-3-phosphate (CHEBI:75110) has functional parent linoleic acid (CHEBI:17351)
1-acyl-2-linoleoyl-sn-glycero-3-phosphocholine betaine (CHEBI:60000) has functional parent linoleic acid (CHEBI:17351)
1-acyl-2-linoleoyl-sn-glycero-3-phosphoethanolamine zwitterion (CHEBI:75069) has functional parent linoleic acid (CHEBI:17351)
1-eicosyl-2-linolenyl-sn-glycero-3-phosphoethanolamine (CHEBI:84535) has functional parent linoleic acid (CHEBI:17351)
1-heptadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine (CHEBI:84566) has functional parent linoleic acid (CHEBI:17351)
1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphoethanolamine (CHEBI:73121) has functional parent linoleic acid (CHEBI:17351)
1-hexadecyl-2-[(9Z,12Z)-octadecadienoyl]-sn-glycero-3-phosphocholine (CHEBI:86231) has functional parent linoleic acid (CHEBI:17351)
1-icosyl-2-[(9Z,12Z)-octadecadienoyl]-sn-glycero-3-phosphocholine (CHEBI:136381) has functional parent linoleic acid (CHEBI:17351)
1-linolenyl-2-linoleyl-PAP (CHEBI:53755) has functional parent linoleic acid (CHEBI:17351)
1-linoleoyl-2-oleoyl-sn-glycero-3-phosphate (CHEBI:74830) has functional parent linoleic acid (CHEBI:17351)
1-linoleoyl-2-oleoylglycerol (CHEBI:75614) has functional parent linoleic acid (CHEBI:17351)
1-linoleoyl-sn-glycero-3-phospho-D-myo-inositol (CHEBI:133077) has functional parent linoleic acid (CHEBI:17351)
1-linoleoyl-sn-glycero-3-phosphocholine (CHEBI:28733) has functional parent linoleic acid (CHEBI:17351)
1-linoleoyl-sn-glycero-3-phosphoethanolamine (CHEBI:83058) has functional parent linoleic acid (CHEBI:17351)
1-linoleoylglycerone 3-phosphate (CHEBI:78173) has functional parent linoleic acid (CHEBI:17351)
1-monolinolein (CHEBI:75568) has functional parent linoleic acid (CHEBI:17351)
1-myristoyl-2-linoleoyl-sn-glycerol (CHEBI:84392) has functional parent linoleic acid (CHEBI:17351)
1-octadecanoyl-2-[(9Z,12Z)-octadecadienoyl]-sn-glycero-3-phosphocholine (CHEBI:84822) has functional parent linoleic acid (CHEBI:17351)
1-oleoyl-2,3-di-linoleoyl-sn-glycerol (CHEBI:84458) has functional parent linoleic acid (CHEBI:17351)
1-oleoyl-2-linoleoyl-sn-glycero-3-phosphate (CHEBI:74849) has functional parent linoleic acid (CHEBI:17351)
1-oleoyl-2-linoleoyl-sn-glycero-3-phospho-L-serine (CHEBI:75096) has functional parent linoleic acid (CHEBI:17351)
1-oleoyl-2-linoleoyl-sn-glycerol (CHEBI:75450) has functional parent linoleic acid (CHEBI:17351)
1-oleoyl-2-linoleyl-sn-glycero-3-phosphoethanolamine (CHEBI:84543) has functional parent linoleic acid (CHEBI:17351)
1-oleoyl-3-linoleoylglycerol (CHEBI:133484) has functional parent linoleic acid (CHEBI:17351)
1-oleyl-2-linoleyl-PAP (CHEBI:53752) has functional parent linoleic acid (CHEBI:17351)
1-palmitoleoyl-2-linoleoyl-sn-glycero-3-phosphocholine (CHEBI:84567) has functional parent linoleic acid (CHEBI:17351)
1-palmitoleoyl-2-linoleoyl-sn-glycerol (CHEBI:84419) has functional parent linoleic acid (CHEBI:17351)
1-palmitoyl-2-linoleoyl-sn-glycerol (CHEBI:82927) has functional parent linoleic acid (CHEBI:17351)
1-palmitoyl-3-linoleoylglycerol (CHEBI:133640) has functional parent linoleic acid (CHEBI:17351)
1-palmityl-2-acetyl-3-linoleoyl-sn-glycerol (CHEBI:77676) has functional parent linoleic acid (CHEBI:17351)
1-pentadecanoyl-2-linoleoyl-sn-glycero-3-phosphocholine (CHEBI:133617) has functional parent linoleic acid (CHEBI:17351)
1-stearoyl-2-linoleoyl-sn-glycero-3-phospho-1D-myo-inositol (CHEBI:77343) has functional parent linoleic acid (CHEBI:17351)
1-stearoyl-2-linoleoyl-sn-glycero-3-phospho-1D-myo-inositol 5-phosphate (CHEBI:77344) has functional parent linoleic acid (CHEBI:17351)
1-stearoyl-2-linoleoyl-sn-glycero-3-phospho-L-serine (CHEBI:84513) has functional parent linoleic acid (CHEBI:17351)
1-stearoyl-2-linoleoyl-sn-glycero-3-phosphoethanolamine (CHEBI:133600) has functional parent linoleic acid (CHEBI:17351)
1-stearoyl-2-linoleoyl-sn-glycerol (CHEBI:77097) has functional parent linoleic acid (CHEBI:17351)
1-tetradecanoyl-2-[(9Z,12Z)-octadecadienoyl]-sn-glycero-3-phosphocholine (CHEBI:86094) has functional parent linoleic acid (CHEBI:17351)
12,13-epoxy-18-hydroxy-(9Z)-octadecenoic acid (CHEBI:138270) has functional parent linoleic acid (CHEBI:17351)
13-hydroperoxylinoleic acid (CHEBI:50097) has functional parent linoleic acid (CHEBI:17351)
18-hydroxylinoleic acid (CHEBI:132472) has functional parent linoleic acid (CHEBI:17351)
2,3-dilinoleoyl-sn-glycerol (CHEBI:75854) has functional parent linoleic acid (CHEBI:17351)
2-hydroxylinoleic acid (CHEBI:136927) has functional parent linoleic acid (CHEBI:17351)
2-linoleoyl-sn-glycero-3-phosphocholine (CHEBI:76084) has functional parent linoleic acid (CHEBI:17351)
2-linoleoyl-sn-glycero-3-phosphoethanolamine (CHEBI:76233) has functional parent linoleic acid (CHEBI:17351)
2-linoleoyl-sn-glycero-3-phosphoethanolamine zwitterion (CHEBI:76090) has functional parent linoleic acid (CHEBI:17351)
2-linoleoylglycerol (CHEBI:75457) has functional parent linoleic acid (CHEBI:17351)
5(S),8(R)-DiHODE (CHEBI:63216) has functional parent linoleic acid (CHEBI:17351)
7(S),8(S)-DiHODE (CHEBI:15658) has functional parent linoleic acid (CHEBI:17351)
7-demethoxyegonol-9(Z),12(Z)linoleate (CHEBI:69547) has functional parent linoleic acid (CHEBI:17351)
8(R)-HPODE (CHEBI:34485) has functional parent linoleic acid (CHEBI:17351)
9,10-epoxy-18-hydroxy-(12Z)-octadecenoic acid (CHEBI:138265) has functional parent linoleic acid (CHEBI:17351)
all-trans-retinyl linoleate (CHEBI:70762) has functional parent linoleic acid (CHEBI:17351)
N,1-dipalmitoyl-2-linoleoyl-sn-glycero-3-phosphoethanolamine (CHEBI:85806) has functional parent linoleic acid (CHEBI:17351)
N-butyryl-1-palmitoyl-2-linoleoyl-sn-glycero-3-phosphoethanolamine (CHEBI:85799) has functional parent linoleic acid (CHEBI:17351)
N-caproyl-1-palmitoyl-2-linoleoyl-sn-glycero-3-phosphoethanolamine (CHEBI:85798) has functional parent linoleic acid (CHEBI:17351)
N-capryl-1-palmitoyl-2-linoleoyl-sn-glycero-3-phosphoethanolamine (CHEBI:85796) has functional parent linoleic acid (CHEBI:17351)
N-capryloyl-1-palmitoyl-2-linoleoyl-sn-glycero-3-phosphoethanolamine (CHEBI:85797) has functional parent linoleic acid (CHEBI:17351)
O-linoleyl-L-carnitine (CHEBI:84098) has functional parent linoleic acid (CHEBI:17351)
CDP-1,2-dilinoleoyl-sn-glycerol (CHEBI:85848) has functional parent linoleic acid (CHEBI:17351)
CDP-1-stearoyl-2-linoleoyl-sn-glycerol (CHEBI:85838) has functional parent linoleic acid (CHEBI:17351)
cholesteryl linoleate (CHEBI:41509) has functional parent linoleic acid (CHEBI:17351)
dilinoleoylglycerol (CHEBI:138658) has functional parent linoleic acid (CHEBI:17351)
egonol-9(Z),12(Z)linoleate (CHEBI:69546) has functional parent linoleic acid (CHEBI:17351)
ethyl linoleate (CHEBI:31572) has functional parent linoleic acid (CHEBI:17351)
HPODE (CHEBI:36329) has functional parent linoleic acid (CHEBI:17351)
laetisaric acid (CHEBI:28932) has functional parent linoleic acid (CHEBI:17351)
linoleamide (CHEBI:82984) has functional parent linoleic acid (CHEBI:17351)
linoleic acid hydroperoxide (CHEBI:78013) has functional parent linoleic acid (CHEBI:17351)
linoleoyl bioconjugate (CHEBI:76186) has functional parent linoleic acid (CHEBI:17351)
linoleoyl ethanolamide (CHEBI:64032) has functional parent linoleic acid (CHEBI:17351)
linoleoyl-sn-glycero-3-phosphocholine (CHEBI:140444) has functional parent linoleic acid (CHEBI:17351)
linoleoyl-containing glycerolipid (CHEBI:88351) has functional parent linoleic acid (CHEBI:17351)
linoleylanilide (CHEBI:53722) has functional parent linoleic acid (CHEBI:17351)
methyl linoleate (CHEBI:69080) has functional parent linoleic acid (CHEBI:17351)
propyl linoleate (CHEBI:91035) has functional parent linoleic acid (CHEBI:17351)
tetralinoleoyl cardiolipin (CHEBI:84398) has functional parent linoleic acid (CHEBI:17351)
trilinoleoyl 2-monolysocardiolipin (CHEBI:84302) has functional parent linoleic acid (CHEBI:17351)
corn oil (CHEBI:195250) has part linoleic acid (CHEBI:17351)
soybean oil (CHEBI:166975) has part linoleic acid (CHEBI:17351)
linoleate (CHEBI:30245) is conjugate base of linoleic acid (CHEBI:17351)
linoleoyl group (CHEBI:32386) is substituent group from linoleic acid (CHEBI:17351)
IUPAC Name
(9Z,12Z)-octadeca-9,12-dienoic acid
Synonyms Sources
(9Z,12Z)-Octadecadienoic acid KEGG COMPOUND
(Z,Z)-9,12-octadecadienoic acid NIST Chemistry WebBook
9-cis,12-cis-Octadecadienoic acid KEGG COMPOUND
9Z,12Z-octadecadienoic acid LIPID MAPS
acide cis-linoléique ChEBI
acide linoléique ChEBI
ácido linoleico ChEBI
all-cis-9,12-octadecadienoic acid ChEBI
C18:2 9c, 12c ω6 todos cis-9,12-octadienoico ChEBI
C18:2, n-6,9 all-cis ChEBI
cis,cis-9,12-octadecadienoic acid ChEBI
cis,cis-linoleic acid ChEBI
cis,cis-linoleic acid NIST Chemistry WebBook
cis-Δ9,12-octadecadienoic acid ChemIDplus
LA ChEBI
Linoleic acid KEGG COMPOUND
LINOLEIC ACID PDBeChem
linolic acid ChEBI
Manual Xrefs Databases
3323 DrugCentral
C00001224 KNApSAcK
C01595 KEGG COMPOUND
EIC PDBeChem
HMDB0000673 HMDB
Linoleic_acid Wikipedia
LINOLEIC_ACID MetaCyc
LMFA01030120 LIPID MAPS
View more database links
Registry Numbers Types Sources
1727101 Reaxys Registry Number Reaxys
57557 Gmelin Registry Number Gmelin
60-33-3 CAS Registry Number KEGG COMPOUND
60-33-3 CAS Registry Number NIST Chemistry WebBook
60-33-3 CAS Registry Number ChemIDplus
Citations Types Sources
11113630 PubMed citation Europe PMC
11304127 PubMed citation Europe PMC
11322990 PubMed citation Europe PMC
14667063 PubMed citation Europe PMC
14993245 PubMed citation Europe PMC
15115315 PubMed citation Europe PMC
15642793 PubMed citation Europe PMC
15969511 PubMed citation Europe PMC
16254037 PubMed citation Europe PMC
16563718 PubMed citation Europe PMC
17647039 PubMed citation Europe PMC
18044828 PubMed citation Europe PMC
18990554 PubMed citation Europe PMC
19628674 PubMed citation Europe PMC
19936816 PubMed citation Europe PMC
23900039 PubMed citation Europe PMC
24081493 PubMed citation Europe PMC
6205897 PubMed citation Europe PMC
Last Modified
31 May 2023
General Comment
2011-01-17 One of two essential fatty acids required by most animals for optimal health.