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


CAS No. :

(S)-(−)-Linoleyl-1/
Product Details
Cat No:R067548
Synonyms:N-((S)-1-hydroxypropan-2-yl)octadeca-9Z,12Z-dienamide
Molecular Formula:C21H39NO2
Molecular Weight:337.5
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Cat No:R067548
Product-Name:(S)-(−)-Linoleyl-1/'-Hydroxy-2/'-Propylamide
InChI:InChI=1S/C21H39NO2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-21(24)22-20(2)19-23/h7-8,10-11,20,23H,3-6,9,12-19H2,1-2H3,(H,22,24)/b8-7-,11-10-/t20-/m0/s1
InChIKey:ADRRUPVKLINJKD-YNLHEVEDSA-N
SMILES:CCCCC/C=CC/C=CCCCCCCCC(N[C@@H](C)CO)=O
N-Acyl ethanolamines (NAEs) have diverse biological actions that are strongly affected by the associated acyl group. Linoleoyl ethanolamide (LOEA) has potential signaling roles in aging and neurological functioning. LOEA has a weak affinity for cannabinoid (CB) receptors (Ki = 10 and 25 μM for CB1 and CB2, respectively). It also inhibits fatty acid amide hydrolase (FAAH; Ki = 9 μM) and is hydrolyzed by FAAH, and inhibits voltage-gated K (S)-(−)-Linoleyl-1’-hydroxy-2’-propylamide is a homolog of LOEA, 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.Lucanic, M.,Held, J.M.,Vantipalli, M.C., et al. N-acylethanolamine signalling mediates the effect of diet on lifespan in Caenorhabditis elegans. Nature 473(7346), 226-229 (2011).
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