(±)5-HEPE


CAS No. : 83952-40-3

(±)5-HEPE,83952-40-3
Product Details
Cat No:R067222
Synonyms:(±)-5-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid
Molecular Formula:C20H30O3
Molecular Weight:318.457
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Cat No:R067222
Cas No:83952-40-3
Product-Name:(±)5-HEPE
IUPAC Name:(6E,8Z,11Z,14Z,17Z)-5-hydroxyicosa-6,8,11,14,17-pentaenoic acid
InChI:InChI=1S/C20H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(21)17-15-18-20(22)23/h3-4,6-7,9-10,12-14,16,19,21H,2,5,8,11,15,17-18H2,1H3,(H,22,23)/b4-3-,7-6-,10-9-,13-12-,16-14+
InChIKey:FTAGQROYQYQRHF-FCWZHQICSA-N
SMILES:CCC=CCC=CCC=CCC=CC=CC(CCCC(=O)O)O
(±)5-HEPE is produced by non-enzymatic oxidation of EPA. It contains equal amounts of 5(S)-HEPE and 5(R)-HEPE. The biological activity of (±)5-HEPE is likely mediated by one of the individual isomers, most commonly the 5(S) isomer in mammalian systems. EPA can be metabolized to 5-HEPE in human and bovine neutrophils, and human eosinophils, which is further metabolized to 5-oxoEPE and LTB5. The 5-series metabolites of EPA, namely 5-HEPE, 5-oxoEPE, and LTB5, have significantly decreased biological effects compared to the arachidonic acid-derived metabolites.
1.Powell, W.S.,Gravel, S. and Gravelle, F. Formation of a 5-oxo metabolite of 5,8,11,14,17-eicosapentaenoic acid and its effects on human neutrophils and eosinophils. Journal of Lipid Research 36, 2590-2598 (1995).
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