(±)12-HEPE


CAS No. : 81187-21-5

(±)12-HEPE,81187-21-5
Product Details
Cat No:R067229
Synonyms:(±)-12-hydroxy-5Z,8Z,10E,14Z,17Z-eicosapentaenoic acid
Molecular Formula:C20H30O3
Molecular Weight:318.457
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Cat No:R067229
Cas No:81187-21-5
Product-Name:(±)12-HEPE
IUPAC Name:(5Z,8Z,10E,14Z,17Z)-12-hydroxyicosa-5,8,10,14,17-pentaenoic acid
InChI:InChI=1S/C20H30O3/c1-2-3-4-5-10-13-16-19(21)17-14-11-8-6-7-9-12-15-18-20(22)23/h3-4,7-11,13-14,17,19,21H,2,5-6,12,15-16,18H2,1H3,(H,22,23)/b4-3-,9-7-,11-8-,13-10-,17-14+
InChIKey:MCRJLMXYVFDXLS-QGQBRVLBSA-N
SMILES:CCC=CCC=CCC(C=CC=CCC=CCCCC(=O)O)O
(±)12-HEPE is produced by non-enzymatic oxidation of EPA. It contains equal amounts of 12(S)-HEPE and 12(R)-HEPE. The biological activity of (±)12-HEPE is likely mediated by one of the individual isomers, most commonly the 12(S) isomer in mammalian systems. 12-HEPE inhibits platelet aggregation with the same potency as 12-HETE, exhibiting IC50 values of 24 and 25 µM, respectively. These compounds are also equipotent as inhibitors of U46619-induced contraction of rat aorta (IC50s = 8.6-8.8 µM).
1.Takenaga, M.,Hirai, A.,Terano, T., et al. Comparison of the in vitro effect of eicosapentaenoic acid (EPA)-derived lipoxygenase metabolites on human platelet function with those of arachidonic acid. Thrombosis Research 37, 373-384 (1986).
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