Oleoylethanolamide
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IUPAC name
(Z)-N-(2-Hydroxyethyl)octadec-9-enamide
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Identifiers | |
111-58-0 | |
ChemSpider | 4446574 |
2661 | |
Jmol 3D model | Interactive image |
PubChem | 5283454 |
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Properties | |
C20H39NO2 | |
Molar mass | 325.54 g·mol−1 |
Appearance | White solid |
Melting point | 59–60 °C (138–140 °F; 332–333 K) |
Solubility in ethanol and DMSO | Soluble |
Vapor pressure | {{{value}}} |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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verify (what is ?) | |
Infobox references | |
Oleoylethanolamine (OEA) is an endogenous peroxisome proliferator-activated receptor alpha (PPAR-α) agonist. It is a naturally occurring ethanolamide lipid that regulates feeding and body weight in vertebrates ranging from mice to pythons.[1][2][3]
OEA is the monounsaturated analogue of the endocannabinoid anandamide, but unlike anandamide it acts independently of the cannabinoid pathway, regulating PPAR-α activity to stimulate lipolysis.[4]
OEA is produced by the small intestine following feeding in two steps. First an N-acyl transferase (NAT) activity joins the free amino terminus of phosphatidylethanolamine (PE) to the oleoyl group (one variety of acyl group) derived from sn-1-oleoyl-phosphatidylcholine, which contains the fatty acid oleic acid at the sn-1 position.[5] This produces an N-acylphosphatidylethanolamine, which is then split (hydrolyzed) by N-acyl phosphatidylethanolamine-specific phospholipase D (NAPE-PLD) into phosphatidic acid and OEA. The biosynthesis of OEA and other bioactive lipid amides is modulated by bile acids.[6]
OEA has been demonstrated to bind to the novel cannabinoid receptor GPR119.[7] OEA has been suggested to be the receptor's endogenous ligand.[8]
OEA has been reported to lengthen the life span of C. elegans through interactions with lysomal molecules.[9]
References
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