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Palmitoyl Serinol

Cayman Chemical Item Number 62175

(CAS 126127-31-9)

Palmitoyl Serinol (CAS 126127-31-9)

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Description

2-Palmitoyl glycerol (2-PG) has been isolated along with the potent endocannabinoid 2-arachidonoyl glycerol (2-AG) from various tissues.1 Although 2-PG displays no intrinsic agonist activity on CB1 or CB2 receptors, it does potentiate the ability of 2-AG to inhibit adenylyl cyclase. 2-PG also potentiates the analgesic, hypokinetic, and anxiolytic effects of 2-AG in mice. This “entourage” effect has been attributed to the ability of compounds such as 2-PG to inhibit reuptake and/or compete with the active endocannabinoids for access to inactivating enzymes such as FAAH and monoglyceride lipase.2,3 Palmitoyl serinol is a stable analog of 2-PG bearing an amide linkage in place of the labile glyceryl ester. This has the potential to enhance its “entourage” activities as a result of a prolonged in vivo half-life. Palmitoyl serinol is also an analog of C-16 ceramide. Incubation of neuroblastoma cells with palmitoyl serinol causes apoptosis with an IC50 of approximately 80 µM.4,5

1 Ben-Shabat, S., Fride, E., Sheskin, T., et al. An entourage effect: Inactive endogenous fatty acid glycerol esters enhance 2-arachidonoyl-glycerol cannabinoid activity. Eur J Pharmacol 353 23-31 (1998).

2 Dinh, T.P., Freund, T.F., and Piomelli, D. A role for monoglyceride lipase in 2-arachidonoylglycerol inactivation. Chem Phys Lipids 121 149-158 (2002).

3 Fowler, C.J., Jonsson, K., and Tiger, G. Fatty acid amide hydrolase: Biochemistry, pharmacology, and therapeutic possibilities for an enzyme hydrolyzing anandamide, 2-arachidonoylglycerol, palmitoylethanolamide, and oleamide. Biochem Pharmacol 62 517-526 (2001).

4 Bieberich, E., Kawaguchi, T., and Yu, R.K. N-acylated serinol is a novel ceramide mimic inducing apoptosis in neuroblastoma cells. J Biol Chem 275 177-181 (2000).

5 Bieberich, E., Hu, B., Silva, J., et al. Synthesis and characterization of novel ceramide analogs for induction of apoptosis in human cancer cells. Cancer Lett 181 55-64 (2002).

Formal Name N-​[2-​hydroxy-​1-​(hydroxymethyl)ethyl]-​hexadecanamide
CAS Number 126127-31-9
Molecular Formula C19H39NO3
Formula Weight 329.5
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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CCCCCCCCCCCCCCCC(NC(CO)​CO)​=O

Background Reading

Fowler, C.J., Jonsson, K., and Tiger, G. Fatty acid amide hydrolase: Biochemistry, pharmacology, and therapeutic possibilities for an enzyme hydrolyzing anandamide, 2-arachidonoylglycerol, palmitoylethanolamide, and oleamide. Biochem Pharmacol 62 517-526 (2001).

Dinh, T.P., Freund, T.F., and Piomelli, D. A role for monoglyceride lipase in 2-arachidonoylglycerol inactivation. Chem Phys Lipids 121 149-158 (2002).

Bieberich, E., Hu, B., Silva, J., et al. Synthesis and characterization of novel ceramide analogs for induction of apoptosis in human cancer cells. Cancer Lett 181 55-64 (2002).

Bieberich, E., Kawaguchi, T., and Yu, R.K. N-acylated serinol is a novel ceramide mimic inducing apoptosis in neuroblastoma cells. J Biol Chem 275 177-181 (2000).

Ben-Shabat, S., Fride, E., Sheskin, T., et al. An entourage effect: Inactive endogenous fatty acid glycerol esters enhance 2-arachidonoyl-glycerol cannabinoid activity. Eur J Pharmacol 353 23-31 (1998).

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Palmitoyl Serinol is available in the following screening library:

Size Price Quantity Subtotal
5 mg $33.00 $0.00
10 mg $63.00 $0.00
50 mg $264.00 $0.00
100 mg $462.00 $0.00
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Cart Total $0.00

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Pricing updated 2012-05-26. Prices are subject to change without notice.

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Warning This product is not for human or veterinary use.

Related Products

2-Arachidonoyl Glycerol
Arachidonoyl Ethanolamide
Arachidonoyl Serinol
Palmitoyl Ethanolamide
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