IUPAC name
ChemSpider  N
Jmol-3D images Image
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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 N  (: YesY/N?)

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]


  1. ^
  2. ^
  3. ^
  4. ^
  5. ^ illustration
  6. ^
  7. ^
  8. ^
  9. ^

External links

  • Science Magazine
  • BBC: Fatty foods 'offer memory boost'