Structure Database (LMSD)

Common Name
Oleoyl-EA(d2)
Systematic Name
N-(9Z-octadecenoyl)-ethanolamine(d2)
Synonyms
  • Oleoyl-ethanolamine(d2)
LM ID
LMFA08040048
Formula
Exact Mass
Calculate m/z
327.310633
Status
Curated

Classification

Biological Context

Oleoyl ethanolamide-d2 (OEA-d2) is intended for use as an internal standard for the quantification of OEA by GC- or LC-MS. OEA is an analogue of the endocannabinoid arachidonoyl ethanolamide (AEA) found in brain tissue and in chocolate.1 It is one of the long chain fatty acid ethanolamides that accumulates rapidly in infarcted tissue, but its biosynthesis is reduced in the intestine of rats following food deprivation.2,3 OEA is an endogenous, potent agonist for peroxisome proliferator-activated receptor α (PPARα), exhibiting an EC50 value of 120 nM in a transactivation assay.4 Systemic administration of OEA suppresses food intake and reduces weight gain in rats (10 mg/kg intraperitoneally) and PPARα wild-type mice, but not in PPARα knockout mice.3,4 These data indicate that OEA regulates food intake by a PPARα-mediated mechanism.

This information has been provided by Cayman Chemical

References

1. Epps, D.E., Palmer, J.W., Schmid, H.H.O., et al. Inhibition of permeability-dependent Ca2+ release from mitochondria by N-acelethanolamines, a class of lipids synthesized in ischemic heart tissue. The Journal of Biological Chemisty 257(3), 1383-1392 (1982).

References

Comments
Synthetic deuterated standard

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
Synthetic deuterated standard

String Representations

InChiKey (Click to copy)
BOWVQLFMWHZBEF-MSKGDGSWSA-N
InChi (Click to copy)
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-/i8D2
SMILES (Click to copy)
C(CCCCCCC/C=C\C([2H])([2H])CCCCCCC)(=O)NCCO

Other Databases

PubChem CID
Cayman ID

Admin

Created at
-
Updated at
29th Jan 2021