(S)-(−)-Eicosapentaenyl-1/'-Hydroxy-2/'-Propylamide


CAS No. :

(S)-(−)-Eicosapentaenyl-1/
Product Details
Cat No:R067540
Synonyms:N-((S)-1-hydroxypropan-2-yl)icosa-5Z,8Z,11Z,14Z,17Z-pentaenamide
Molecular Formula:C23H37NO2
Molecular Weight:359.6
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Cat No:R067540
Product-Name:(S)-(−)-Eicosapentaenyl-1/'-Hydroxy-2/'-Propylamide
InChI:InChI=1S/C23H37NO2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-23(26)24-22(2)21-25/h4-5,7-8,10-11,13-14,16-17,22,25H,3,6,9,12,15,18-21H2,1-2H3,(H,24,26)/b5-4-,8-7-,11-10-,14-13-,17-16-/t22-/m0/s1
InChIKey:XOYVLIGJHWVUFH-ZVBGTZBRSA-N
SMILES:CC/C=CC/C=CC/C=CC/C=CC/C=CCCCC(N[C@@H](C)CO)=O
N-Acyl ethanolamines (NAEs) have diverse biological actions that are strongly affected by the associated acyl group. Eicosapentaenoyl ethanolamide (EPEA) has potential signaling roles in aging, cancer, inflammation, and neurological development. At least some of EPEA’s effects are mediated through cannabinoid (CB) receptors, while some NAEs also act as vanilloid receptor agonists. S-(−)-Eicosapentaenyl-1’-hydroxy-2’-propylamide is a homolog of EPEA, characterized by the addition of an (S)-α-methyl group at the methylene carbon adjacent to the amide nitrogen. A similar modification of arachidonoyl ethanolamide (Item No. 90050) to produce S-1 methanandamide (Item No. 90072) results in a diminished affinity for the CB receptor but greatly improved metabolic stability to aminopeptidase hydrolysis. The physiological actions of this compound have not been evaluated.
1.Brown, I.,Cascio, M.G.,Wahle, K.W.J., et al. Cannabinoid receptor-dependent and -independent anti-proliferative effects of omega-3 ethanolamides in androgen receptor-positive and -negative prostate cancer cell lines. Carcinogenesis 31(9), 1584-1591 (201
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