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

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+ channels. 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)-beta-methyl group at the terminal ethanolamine carbon. A similar modification of arachidonoyl ethanolamide (Cay-90050) to produce R-2 methanandamide (Cay-90074) imparts diminished affinity for the CB receptor as well as reduced metabolic stability. The physiological actions of this compound have not been evaluated.Formal Name: N-((R)-2-hydroxypropyl)octadeca-9Z,12Z-dienamide. Molecular Formula: C21H39NO2. Formula Weight: 337.5. Purity: >98%. Formulation: (Request formulation change), A solution in ethanol. Solubility: DMF: 11 mg/ml, DMSO: 5 mg/ml, Ethanol: 20 mg/ml, Ethanol:PBS (pH 7.2)(1:2): 11 mg/ml. SMILES: CCCCC/C=C\C/C=C\CCCCCCCC(NC[C@@H](C)O)=O. InChi Code: 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. InChi Key: QWQYZEAVCOQEQB-FNUGXZCYSA-N.