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Glycerophospho-N-Oleoyl Ethanolamine (CAS 201738-24-1) LS-H58

PPAR alpha agonist
LS-H58-1 / 1 mg / $205
LS-H58-5 / 5 mg / $375
LS-H58-10 / 10 mg / $560
USA Shipment Only
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Description: N-Acylated ethanolamines (NAE) are naturally-occurring lipids that have diverse bioactivities. For example, arachidonoyl ethanolamide (AEA) is an endogenous cannabinoid neurotransmitter that evokes cellular responses by activating the cannabinoid receptors, central cannabinoid (CB1) and peripheral cannabinoid (CB2). The different types of NAE are derived from glycerophospho-linked precursors by the activity of glycerophosphodiesterase 1 (GDE1). Glycerophospho-N-oleoyl ethanolamine is the precursor of oleoyl ethanolamide (OEA). OEA is an endogenous, potent agonist for PPAR alpha, exhibiting an EC50 value of 120 nM in a transactivation assay. Systemic administration of OEA suppresses food intake and reduces weight gain in rats (10 mg/kg intraperitoneally) and PPAR alpha wild-type mice, but not in PPAR alpha knockout mice. Like AEA, OEA is metabolized by fatty acid amide hydrolase (FAAH). H58_ChemicalStructureImage.png
mono(2,3-dihydroxypropyl)-mono[2-[[(9Z)-1-oxo-9-octadecenyl]amino]ethyl] ester phosphoric acid
 
biochemical, chemical, agonist
LS-H58
201738-24-1
C23H46NO7P
≥98%
A crystalline solid
0
CCCCCCCC/C=C\CCCCCCCC(=O)NCCOP(=O)(O)OCC(O)CO
InChI=1S/C23H46NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-23(27)24-18-19-30-32(28,29)31-21-22(26)20-25/h9-10,22,25-26H,2-8,11-21H2,1H3,(H,24,27)(H,28,29)/b10-9-
VBNXVCGZJCGEKO-KTKRTIGZSA-N
Shipped Ambient, store at -20°C, ≥ 2 years shelf life.
This product is for research use only. Not for administration to humans, or for human or veterinary diagnostic or therapeutic use.
Data Sheet DataSheet    SDS SDS
Related Products: PPARA / PPAR Alpha related products

Usage Information

Glycerophospho-N-oleoyl ethanolamine is supplied as a crystalline solid. A stock solution may be made by dissolving the glycerophospho-N-oleoyl ethanolamine in an organic solvent purged with an inert gas. Glycerophospho-N-oleoyl ethanolamine is soluble in organic solvents such as ethanol, DMSO, and dimethyl formamide. The solubility of glycerophospho-N-oleoyl ethanolamine in these solvents is approximately 20 mg/ml. Further dilutions of the stock solution into aqueous buffers or isotonic saline should be made prior to performing biological experiments. Ensure that the residual amount of organic solvent is insignificant, since organic solvents may have physiological effects at low concentrations. Organic solvent-free aqueous solutions of glycerophospho-N-oleoyl ethanolamine can be prepared by directly dissolving the crystalline compound in aqueous buffers. The solubility of glycerophospho-N-oleoyl ethanolamine in PBS, pH 7.2, is approximately 10 mg/ml. We do not recommend storing the aqueous solution for more than one day.

References:
  1. Simon, G.M. and Cravatt, B.F. Anandamide biosynthesis catalyzed by the phosphodiesterase GDE1 and detection of glycerophospho-N-acyl ethanolamine precursors in mouse brain. J. Biol. Chem. 283, 9341-9349 (2008).
  2. Fu, J., Gaetani, S., Oveisi, F., et al. Oleylethanolamide regulates feeding and body weight through activation of the nuclear receptor PPARα. Nature 425, 90-93 (2003).
  3. de Fonseca, F.R., Navarro, M., Gómez, R., et al. An anorexic lipid mediator regulated by feeding. Nature 414, 209-212 (2001).

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