An internal standard for the quantification of oleoyl ethanolamide
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Alternative(s)
10007823Oleoyl Ethanolamide-d2
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Oleoyl Ethanolamide-d4

Item No. 9000552

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-(2-hydroxyethyl-1',1,2,2'-d4)-9Z-octadecenamide
CAS Number
946524-36-3
Synonyms
  • OEA-d4
  • Oleic Acid Ethanolamide-d4
Molecular Formula
C20H35D4NO2
Formula Weight
329.6
Purity
≥99% deuterated forms (d1-d4)
Formulation
A 1 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 100 mg/mlDMSO: 100 mg/mlEthanol: 100 mg/mlPBS (pH 7.2): 100 µg/ml
SMILES
CCCCCCCC\C=C/CCCCCCCC(N([H])C([2H])([2H])C([2H])([2H])O)=O
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-/i18D2,19D2
InChi Key
BOWVQLFMWHZBEF-QAFBOUAWSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

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    100 µg

    $42

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    500 µg

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    1 mg

    $315

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    5 mg

    $1,365

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    Product Description

    Oleoyl ethanolamide-d4 contains four deuterium atoms at the hydroxyethyl 1,1',2, and 2' positions. It is intended for use as an internal standard for the quantification of oleoyl ethanolamide by GC- or LC-mass spectrometry. 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).