(R)-(−)-Docosahexaenyl-2'-Hydroxy-1'-Propylamide

• CAT Number: R067542
• Molecular Formula: C25H39NO2
• Molecular Weight: 385.6
• Purity: ≥95%
• Synonyms: N-((R)-2-hydroxypropyl)docosa-4Z,7Z,10Z,13Z,16Z,19Z-hexaenamide
• Storage: -20°C
• InChI: InChI=1S/C25H39NO2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-25(28)26-23-24(2)27/h4-5,7-8,10-11,13-14,16-17,19-20,24,27H,3,6,9,12,15,18,21-23H2,1-2H3,(H,26,28)/b5-4-,8-7-,11-10-,14-13-,17-16-,20-19-/t24-/m1/s1
• InChIKey: YYWKDWHNOALABR-BSBZWLAMSA-N
• SMILES: CC/C=CC/C=CC/C=CC/C=CC/C=CC/C=CCCC(NC[C@@H](C)O)=O

N-<wbr></wbr>Acyl ethanolamines (NAEs) have diverse biological actions that are strongly affected by the associated acyl group. Docosahexaenoyl ethanolamide (DHEA) has potential signaling roles in cancer, inflammation, and neurological development and functioning. At least some of DHEA’s effects are mediated through cannabinoid (CB) receptors, while some NAEs also act as vanilloid receptor agonists and voltage-<wbr></wbr>gated K (R)-<wbr></wbr>(−)-<wbr></wbr>Docosahexaenyl-<wbr></wbr>2’-<wbr></wbr>hydroxy-<wbr></wbr>1’-<wbr></wbr>propylamide is a homolog of DHEA, characterized by the addition of an (R)-<wbr></wbr>β-<wbr></wbr>methyl group at the terminal ethanolamine carbon. A similar modification of arachidonoyl ethanolamide (Item No. 90050) to produce R-<wbr></wbr>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.

Reference

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