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.
Read full article at Wikipedia
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
cis9,12-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
Choque B, Catheline D, Rioux V, Legrand P (2014)
Linoleic acid: between doubts and certainties.
Biochimie 96, 14-21 [PubMed:23900039]
[show Abstract]
Alvheim AR, Torstensen BE, Lin YH, Lillefosse HH, Lock EJ, Madsen L, Frøyland L, Hibbeln JR, Malde MK (2014)
Dietary linoleic acid elevates the endocannabinoids 2-AG and anandamide and promotes weight gain in mice fed a low fat diet.
Lipids 49, 59-69 [PubMed:24081493]
[show Abstract]
Nomura T, Horikawa M, Shimamura S, Hashimoto T, Sakamoto K (2010)
Fat accumulation in Caenorhabditis elegans is mediated by SREBP homolog SBP-1.
Genes & nutrition 5, 17-27 [PubMed:19936816]
[show Abstract]
IBD in EPIC Study Investigators, Tjonneland A, Overvad K, Bergmann MM, Nagel G, Linseisen J, Hallmans G, Palmqvist R, Sjodin H, Hagglund G, Berglund G, Lindgren S, Grip O, Palli D, Day NE, Khaw KT, Bingham S, Riboli E, Kennedy H, Hart A (2009)
Linoleic acid, a dietary n-6 polyunsaturated fatty acid, and the aetiology of ulcerative colitis: a nested case-control study within a European prospective cohort study.
Gut 58, 1606-1611 [PubMed:19628674]
[show Abstract]
Whelan J (2008)
The health implications of changing linoleic acid intakes.
Prostaglandins, leukotrienes, and essential fatty acids 79, 165-167 [PubMed:18990554]
[show Abstract]
Haddada FM, Manaï H, Oueslati I, Daoud D, Sánchez J, Osorio E, Zarrouk M (2007)
Fatty acid, triacylglycerol, and phytosterol composition in six Tunisian olive varieties.
Journal of agricultural and food chemistry 55, 10941-10946 [PubMed:18044828]
[show Abstract]
Pérez-Matute P, Martínez JA, Marti A, Moreno-Aliaga MJ (2007)
Linoleic acid decreases leptin and adiponectin secretion from primary rat adipocytes in the presence of insulin.
Lipids 42, 913-920 [PubMed:17647039]
[show Abstract]
Feng DD, Luo Z, Roh SG, Hernandez M, Tawadros N, Keating DJ, Chen C (2006)
Reduction in voltage-gated K+ currents in primary cultured rat pancreatic beta-cells by linoleic acids.
Endocrinology 147, 674-682 [PubMed:16254037]
[show Abstract]
Hennig B, Lei W, Arzuaga X, Ghosh DD, Saraswathi V, Toborek M (2006)
Linoleic acid induces proinflammatory events in vascular endothelial cells via activation of PI3K/Akt and ERK1/2 signaling.
The Journal of nutritional biochemistry 17, 766-772 [PubMed:16563718]
[show Abstract]
Tritt KL, O'Bara CJ, Wells MJ (2005)
Chemometric discrimination among wild and cultured age-0 largemouth bass, black crappies, and white crappies based on fatty acid composition.
Journal of agricultural and food chemistry 53, 5304-5312 [PubMed:15969511]
[show Abstract]
Cheng Z, Elmes M, Kirkup SE, Chin EC, Abayasekara DR, Wathes DC (2005)
The effect of a diet supplemented with the n-6 polyunsaturated fatty acid linoleic acid on prostaglandin production in early- and late-pregnant ewes.
The Journal of endocrinology 184, 165-178 [PubMed:15642793]
[show Abstract]
Namazi MR (2004)
The beneficial and detrimental effects of linoleic acid on autoimmune disorders.
Autoimmunity 37, 73-75 [PubMed:15115315]
[show Abstract]
Saraswathi V, Wu G, Toborek M, Hennig B (2004)
Linoleic acid-induced endothelial activation: role of calcium and peroxynitrite signaling.
Journal of lipid research 45, 794-804 [PubMed:14993245]
[show Abstract]
Ramadan MF, Mörsel JT (2003)
Determination of the lipid classes and fatty acid profile of Niger (Guizotia abyssinica Cass.) seed oil.
Phytochemical analysis : PCA 14, 366-370 [PubMed:14667063]
[show Abstract]
Wulferink M, González J, Goebel C, Gleichmann E (2001)
T cells ignore aniline, a prohapten, but respond to its reactive metabolites generated by phagocytes: possible implications for the pathogenesis of toxic oil syndrome.
Chemical research in toxicology 14, 389-397 [PubMed:11304127]
[show Abstract]
Spiteller G (2001)
Peroxidation of linoleic acid and its relation to aging and age dependent diseases.
Mechanisms of ageing and development 122, 617-657 [PubMed:11322990]
[show Abstract]
Fitch CD, Cai GZ, Shoemaker JD (2000)
A role for linoleic acid in erythrocytes infected with Plasmodium berghei.
Biochimica et biophysica acta 1535, 45-49 [PubMed:11113630]
[show Abstract]
Marquet A, Larraga V, Diez JL, Amela C, Rodrigo J, Muñoz E, Pestaña A (1984)
Immunogenicity of fatty acid anilides in rabbits and the pathogenesis of the Spanish toxic oil syndrome.
Experientia 40, 977-980 [PubMed:6205897]
[show Abstract]
Last Modified
31 May 2023
General Comment
2011-01-17 One of two essential fatty acids required by most animals for optimal health.