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 ChemicalBook:CB9125821, eMolecules:524840, eMolecules:26755855, ZINC000004474613
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Linoleic acid (LA) is an organic compound with the formula HOOC(CH2)7CH=CHCH2CH=CH(CH2)4CH3. Both alkene groups (−CH=CH−) are cis. It is a fatty acid sometimes denoted 18:2 (n−6) or 18:2 cis-9,12. A linoleate is a salt or ester of this acid. Linoleic acid is a polyunsaturated, omega−6 fatty acid. It is a colorless liquid that is virtually insoluble in water but soluble in many organic solvents. It typically occurs in nature as a triglyceride (ester of glycerin) rather than as a free fatty acid. It is one of two essential fatty acids for humans, who must obtain it through their diet, and the most essential, because the body uses it as a base to make the others. The word "linoleic" derives from Latin linum 'flax' and oleum 'oil', reflecting the fact that it was first isolated from linseed oil.
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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 Waiting for Citations
Last Modified
31 May 2023
General Comment
2011-01-17 One of two essential fatty acids required by most animals for optimal health.