Oleoyl Ethanolamide

Oleoyl Ethanolamide

Cayman Chemical Item Number 90265

Oleic Acid Ethanolamide; OEA (CAS 111-58-0)

Oleoyl Ethanolamide (CAS 111-58-0)

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.

1 di Tomaso, E., Beltramo, M., and Piomelli, D. Brain cannabinoids in chocolate. Nature 382 677-678 (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. J Biol Chem 257 1383-1392 (1982).

3 de Fonseca, F.R., Navarro, M., Gómez, R., et al. An anorexic lipid mediator regulated by feeding. Nature 414 209-212 (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 90-93 (2003).

Synonyms

Oleic Acid Ethanolamide
OEA

Formal Name

N-(2-hydroxyethyl)-9Z-octadecenamide

CAS Number

111-58-0

Molecular Formula

C₂₀H₃₉NO₂

Formula Weight

325.5

Formulation

A crystalline solid

Purity

≥98%

Stability

1 year

Storage

-20°C

Shipping

Room temperature in continental US; may vary elsewhere

SMILES

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CCCCCCCC/C=C\CCCCCCCC(=O)NCCO

Background Reading

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

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

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. J Biol Chem 257 1383-1392 (1982).

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

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Oleoyl Ethanolamide is available in the following screening library:

Bio-active Lipid I Screening Library (96-Well)

Size

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