Oleoylethanolamide

Source: Wikipedia, the free encyclopedia.
Oleoylethanolamide
Names
Preferred IUPAC name
(9Z)-N-(2-Hydroxyethyl)octadec-9-enamide
Identifiers
3D model (
JSmol
)
ChEBI
ChemSpider
ECHA InfoCard
 100.003.532 Edit this at Wikidata
IUPHAR/BPS
UNII
  • 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 325.537 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 their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Oleoylethanolamide (OEA) is an

vertebrates ranging from mice to pythons.[1][2][3]

OEA is a shorter, monounsaturated

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

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 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 roundworm Caenorhabditis elegans through interactions with lysomal molecules.[10]

References

  1. PMID 12700681
    .
  2. S2CID 26838764
    .
  3. S2CID 11852711
    .
  4. PMID 19011363
    .
  5. ^ illustration
  6. PMID 25684574
    .
  7. PMID 16517404
    .
  8. PMID 17906678
    .
  9. PMID 33292302
    .
  10. PMID 25554789
    .

External links