An endogenous, potent agonist for PPARα
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Labeled Version(s)
10007823Oleoyl Ethanolamide-d2
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Oleoyl Ethanolamide

Item No. 90265

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-(2-hydroxyethyl)-9Z-octadecenamide
CAS Number
111-58-0
Synonyms
  • Oleic Acid Ethanolamide
  • OEA
Molecular Formula
C20H39NO2
Formula Weight
325.5
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
basic PBS: 100 µg/mlDMF: 100 mg/mlDMSO: 100 mg/mlEtOH: 100 mg/mlPBS pH 7.2: 100 µg/ml
SMILES
CCCCCCCC/C=C\CCCCCCCC(=O)NCCO
InChi Code
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-
InChi Key
BOWVQLFMWHZBEF-KTKRTIGZSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    100 mg

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    Cayman Chemical
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    OBESITY RESEARCH SOLUTIONS
    Product Description

    Oleoyl ethanolamide (OEA) is an analog of the endocannabinoid 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,2 but its biosynthesis is reduced in the intestine of rats following food deprivation.3 OEA is an endogenous, potent agonist for 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.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. di Tomaso, E., Beltramo, M., and Piomelli, D. Brain cannabinoids in chocolate. Nature 382(6593), 677-678 (1996).

    2. 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).

    3. de Fonseca, F.R., Navarro, M., Gómez, R., et al. An anorexic lipid mediator regulated by feeding. Nature 414(6860), 209-212 (2001).

    4. Fu, J., Gaetani, S., Oveisi, F., et al. Oleylethanolamide regulates feeding and body weight through activation of the nuclear receptor PPAR-α. Nature 425(6953), 90-93 (2003).

    Product Citations

    Gouveia-Figueira, S., Karlsson, J., Deplano, A., et al. Characterisation of (R)-2-(2-fluorobiphenyl-4-yl)-N-(3-methylpyridin-2-yl)propanamide as a dual fatty acid amide hydrolase: Cyclooxygenase inhibitor. PLoS One 10(9), e0139212 (2015).