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


CAS No. :

(R)-(−)-Linoleyl-2/
Product Details
Cat No:R067546
Synonyms:N-((R)-2-hydroxypropyl)octadeca-9Z,12Z-dienamide
Molecular Formula:C21H39NO2
Molecular Weight:337.5
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Cat No:R067546
Product-Name:(R)-(−)-Linoleyl-2/'-Hydroxy-1/'-Propylamide
InChI:InChI=1S/C21H39NO2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-21(24)22-19-20(2)23/h7-8,10-11,20,23H,3-6,9,12-19H2,1-2H3,(H,22,24)/b8-7-,11-10-/t20-/m1/s1
InChIKey:QWQYZEAVCOQEQB-FNUGXZCYSA-N
SMILES:CCCCC/C=CC/C=CCCCCCCCC(NC[C@@H](C)O)=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, 25 μM for CB1, CB2, respectively) and inhibits voltage-gated K LOEA also inhibits fatty acid amide hydrolase (FAAH; Ki = 9 μM) and is hydrolyzed by FAAH. (R)-(−)-Linoleyl-2’-hydroxy-1’-propylamide is a homolog of LOEA which is characterized by the addition of an (R)-β-methyl group at the terminal ethanolamine carbon. A similar modification of arachidonoyl ethanolamide (Item No. 90050) to produce R-2 methanandamide (Item No. 90074) imparts diminished affinity for the CB receptor as well as reduced metabolic stability. 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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