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Prostaglandin D2-1-glyceryl ester

Cayman Chemical Item Number 12015

PGD2-1-glyceryl ester (CAS 309260-52-4)

Prostaglandin D2-1-glyceryl ester (CAS 309260-52-4)

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Description

2-Arachidonoyl glycerol (2-AG) has been isolated from porcine brain, and has been characterized as the natural endocannabinoid ligand for the CB1 receptor.1,2 Incubation of 2-AG with cyclooxygenase-2 (COX-2) and specific prostaglandin H2 (PGH2) isomerases in cell cultures and isolated enzyme preparations results in prostaglandin glycerol ester formation.3 The biosynthesis of PGH, PGD, PGE, PGF, and TXA-2-glyceryl ester compounds have all been documented. In RAW 264.7 cells, PGD2-2-glyceryl ester is the main COX metabolite.3 The 2-glyceryl ester moiety equilibrates rapidly (within minutes) with the more stable 1-glyceryl ester, producing a 10:90 mixture of the 1- and 2-glyceryl esters in typical aqueous media. While the stability and metabolism of these PG products have been investigated, little is known about their intrinsic biological activity.4

1 Sugiura, T., Kodaka, T., Kondo, S., et al. 2-Arachidonoylglycerol, a putative endogenous cannabinoid receptor ligand, induces rapid, transient elevation of intracellular free Ca2+ in neuroblastoma X glioma hybrid NG108-15 cells. Biochem Biophys Res Commun 229 58-64 (1996).

2 Sugiura, T., Kodaka, T., Kondo, S., et al. Is the cannabinoid CB1 receptor a 2-arachidonoylglycerol receptor? Structural requirements for triggering a Ca2+ transient in NG108-15 cells. J Biochem 122 890-895 (1997).

3 Kozak, K.R., Crews, B.C., Morrow, J.D., et al. Metabolism of the endocannabinoids, 2-arachidonylgycerol and anandamide, into prostaglandin, thromboxane, and prostacyclin glycerol esters and ethanolamides. J Biol Chem 277(47) 44877-44885 (2002).

4 Kozak, K.R., Crews, B.C., Ray, J.L., et al. Metabolism of prostaglandin glycerol esters and prostaglandin ethanolamides in vitro and in vivo. J Biol Chem 276(40) 36993-36998 (2001).

Synonyms
  • PGD2-1-glyceryl ester
Formal Name 9α,​15S-​dihydroxy-​11-​oxo-​prosta-​5Z,​13E-​dien-​1-​oic acid,​ 1-​glyceryl ester
CAS Number 309260-52-4
Molecular Formula C23H38O7
Formula Weight 426.6
Formulation A solution in acetonitrile
Purity >95% (as a 9:1 mixture of the 1- and 2-glyceryl esters)
Stability 1 year
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES
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CCCCCC(O)​/C=C/[C@H]​1C(=O)​CC(O)​C1C/C=C\CCCC(=O)​OCC(O)​CO

Background Reading

Sugiura, T., Kodaka, T., Kondo, S., et al. 2-Arachidonoylglycerol, a putative endogenous cannabinoid receptor ligand, induces rapid, transient elevation of intracellular free Ca2+ in neuroblastoma X glioma hybrid NG108-15 cells. Biochem Biophys Res Commun 229 58-64 (1996).

Sugiura, T., Kodaka, T., Kondo, S., et al. Is the cannabinoid CB1 receptor a 2-arachidonoylglycerol receptor? Structural requirements for triggering a Ca2+ transient in NG108-15 cells. J Biochem 122 890-895 (1997).

Kozak, K.R., Crews, B.C., Morrow, J.D., et al. Metabolism of the endocannabinoids, 2-arachidonylgycerol and anandamide, into prostaglandin, thromboxane, and prostacyclin glycerol esters and ethanolamides. J Biol Chem 277(47) 44877-44885 (2002).

Kozak, K.R., Crews, B.C., Ray, J.L., et al. Metabolism of prostaglandin glycerol esters and prostaglandin ethanolamides in vitro and in vivo. J Biol Chem 276(40) 36993-36998 (2001).

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Prostaglandin D2-1-glyceryl ester is available in the following screening libraries:

Size Price Quantity Subtotal
1 mg $69.00 $0.00
5 mg $311.00 $0.00
10 mg $552.00 $0.00
50 mg $2,415.00 $0.00
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Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

Please contact our Sales Department for a quote or to purchase.

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

To ask for assistance with one of our products please contact a Technical Support Scientist.

Warning This product is not for human or veterinary use.

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Prostaglandin E2-1-glyceryl ester
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