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Glycerophospho-N-Oleoyl Ethanolamine

Catalog No.GC14531

precursor of oleoyl ethanolamide (OEA)

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Glycerophospho-N-Oleoyl Ethanolamine Chemical Structure

Cas No.: 201738-24-1

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1mg
$117.00
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5mg
$520.00
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10mg
$920.00
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Sample solution is provided at 25 µL, 10mM.

Product Documents

Quality Control & SDS

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Background

Glycerophospho-N-Oleoyl Ethanolamine is the precursor of oleoyl ethanolamide (OEA). The fatty-acid ethanolamide, oleoylethanolamide (OEA) is a naturally occurring lipid. Oleoylethanolamide is an endogenous PPAR-α agonist. Oleoylethanolamide has been involved in modulating feeding and energy homeostasis by binding to peroxisome proliferator-activated receptor-alpha (PPAR-α) [1]. PPAR-α is a transcription factor and a major regulator of lipid metabolism in the liver. Activation of PPAR-α is mainly involved in fatty acid oxidation and expressed in liver, kidney, and skeletal muscle. Through ligand binding, PPAR-α promotes uptake, utilization, and catabolism of fatty acids [2].

OEA reduced food intake and lowered body-weight gain. Subchronic OEA treatment (5 mg/kg, i.p., once daily for two weeks) in Zucker rats initiated transcription of PPAR-α and other PPAR-α target gene [1]. OEA is an endogenous, potent agonist for PPARα. OEA activated PPARα with an EC50 value of 120 nM in a transactivation assay [3]. In rodents, intraperitoneal administration of OEA induced satiety and peripheral utilization of lipid substrate. Acute oral administration induced satiety [4].

References:
[1] Fu J, Oveisi F, Gaetani S, et al.  Oleoylethanolamide, an endogenous PPAR-α agonist, lowers body weight and hyperlipidemia in obese rats[J]. Neuropharmacology, 2005, 48(8): 1147-1153.
[2] Schiffrin E L, Amiri F, Benkirane K, et al.  Peroxisome proliferator-activated receptors[J]. Hypertension, 2003, 42(4): 664-668.
[3] Fu J, Gaetani S, Oveisi F, et al.  Oleylethanolamide regulates feeding and body weight through activation of the nuclear receptor PPAR-α[J]. Nature, 2003, 425(6953): 90-93.
[4] Thabuis C, Destaillats F, Tissot‐Favre D, et al.  Oleoyl‐ethanolamide (OEA): A bioactive lipid derived from oleic acid and phosphatidylethanol‐amine[J]. Lipid Technology, 2007, 19(10): 225-227.

Chemical Properties

Cas No. 201738-24-1 SDF
Chemical Name mono(2,3-dihydroxypropyl)-mono[2-[[(9Z)-1-oxo-9-octadecenyl]amino]ethyl] ester phosphoric acid
Canonical SMILES CCCCCCCC/C=C\CCCCCCCC(=O)NCCOP(=O)(O)OCC(O)CO
Formula C23H46NO7P M.Wt 479.6
Solubility ≤20mg/ml in ethanol;20mg/ml in DMSO;20mg/ml in dimethyl formamide Storage Store at -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table

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1 mg 5 mg 10 mg
1 mM 2.0851 mL 10.4254 mL 20.8507 mL
5 mM 0.417 mL 2.0851 mL 4.1701 mL
10 mM 0.2085 mL 1.0425 mL 2.0851 mL
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Average Rating: 5 ★★★★★ (Based on Reviews and 25 reference(s) in Google Scholar.)

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