Oleoylethanolamide

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Oleoylethanolamide
Oea.svg
Names
IUPAC name
(Z)-N-(2-Hydroxyethyl)octadec-9-enamide
Identifiers
111-58-0 YesY
ChemSpider 4446574 N
2661
Jmol 3D model Interactive image
PubChem 5283454
  • InChI=1S/C20H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h9-10,22H,2-8,11-19H2,1H3,(H,21,23)/b10-9- N
    Key: BOWVQLFMWHZBEF-KTKRTIGZSA-N N
  • InChI=1/C20H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h9-10,22H,2-8,11-19H2,1H3,(H,21,23)/b10-9-
    Key: BOWVQLFMWHZBEF-KTKRTIGZBW
  • CCCCCCCC\C=C/CCCCCCCC(=O)NCCO
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).
N verify (what is YesYN ?)
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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External links

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  5. ↑ illustration
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