 | |
| Names | |
|---|---|
| Preferred IUPAC name (9Z)-N-(2-Hydroxyethyl)octadec-9-enamide | |
| Identifiers | |
| |
3D model (JSmol) | |
| ChEBI | |
| ChemSpider |
|
| ECHA InfoCard | 100.003.532 |
| UNII | |
| |
| |
| Properties | |
| C20H39NO2 | |
| Molar mass | 325.537 g·mol−1 |
| Appearance | White solid |
| Melting point | 59–60 °C (138–140 °F; 332–333 K) |
| Solubility in ethanol and DMSO | Soluble |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Oleoylethanolamide (OEA) is anendogenousperoxisome proliferator-activated receptor alpha (PPAR-α)agonist. It is a naturally occurringethanolamide lipid that regulates feeding and body weight invertebrates ranging from mice to pythons.[1][2][3]
OEA is a shorter, monounsaturatedanalogue of theendocannabinoidanandamide, but unlike anandamide it acts independently of the cannabinoid pathway, regulating PPAR-α activity to stimulatelipolysis.[4]
OEA is produced by thesmall intestine following feeding in two steps. First anN-acyl transferase (NAT) activity joins the free amino terminus ofphosphatidylethanolamine (PE) to theoleoyl group (one variety ofacyl group) derived fromsn-1-oleoyl-phosphatidylcholine, which contains thefatty acidoleic acid at the sn-1 position.[5] This produces anN-acylphosphatidylethanolamine, which is then split (hydrolyzed) byN-acyl phosphatidylethanolamine-specific phospholipase D (NAPE-PLD) intophosphatidic acid and OEA. The biosynthesis of OEA and other bioactive lipid amides is modulated bybile acids.[6]
OEA has been demonstrated to bind to the novelcannabinoid receptorGPR119.[7] OEA has been suggested to be the receptor's endogenous ligand.[8]
OEA has been hypothesized to play a key role in the inhibition of food seeking behavior and in the lipolysis of brown bears "ursus arctos" during the hibernation season together with the alteration of the endocannabinoid system required for the metabolic changes for hibernation.[9]
OEA has been reported to lengthen the life span of the roundwormCaenorhabditis elegans through interactions with lysomal molecules.[10]
OEA is mainly known by its anorexigenic effects. However, it has also neuroprotective properties. In this sense, recent research has demonstrated that OEA reduces neuronal death in a murine model of aggressive neurodegeneration.[11] Such neuroprotective effect is triggered by a stabilization of microtubule dynamics and by the modulation of neuroinflammation[12]
