Oleoylethanolamine

Oleoylethanolamide
Names

IUPAC name (Z)-N-(2-Hydroxyethyl)octadec-9-enamide
Identifiers
CAS Number	111-58-0^Y
3D model (JSmol)	Interactive image
ChemSpider	4446574^N
ECHA InfoCard	100.003.532
IUPHAR/BPS	2661
PubChem CID	5283454
InChI 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
SMILES CCCCCCCC\C=C/CCCCCCCC(=O)NCCO
Properties
Chemical formula	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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N (what is ^YN ?)
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.

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.

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. 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.

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Wikipedia