11-deoxy-11-methylene Prostaglandin D2

Cayman Chemical Item Number 12410

11-deoxy-11-methylene PGD2 (CAS 100648-29-1)

11-deoxy-11-methylene Prostaglandin D2 (CAS 100648-29-1)

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Description

Prostaglandin D2 (PGD2) is one of the five primary enzymatic prostaglandins derived directly from PGH2. PGD2 is produced abundantly in the CSF by the lipocalin-type PGD synthase, and in the periphery by myeloid cells including mast cells and basophils by a second, leukocyte-type PGD synthase.1 PGD2 is chemically unstable, and its use and analysis is complicated by its short in vivo half-life. 11-deoxy-11-methylene PGD2 is a novel, chemically stable, isosteric analog of PGD2 wherein the 11-keto group is replaced by an exocyclic methylene. In the PGE series, the analogous modification leads to a stable, somewhat less potent agonist which embodies the same uterine stimulant and cervical ripening activities as the parent prostaglandin.2 However, 11-deoxy-11-methylene PGD2 has been reported by one group to be essentially without agonist activity on human platelets, a DP1 receptor assay.3 The CRTH2-receptor actions of 11-deoxy-11-methylene PGD2 are not yet reported.

1 Urade, Y., and Hayaishi, O. Prostaglandin D synthase: Structure and function. Vitam Horm 58 89-120 (2000).

2 Borten, M., DiLeo, L.A., and Friedman, E.A. Low-dose prostaglandin E2 analogue for cervical dilations prior to pregnancy termination. Am J Obstet Gynecol 150 561-565 (1984).

3 Torisawa, Y., Yamaguchi, T., Sakata, S., et al. Synthesis of 11-deoxo-11-methylene-prostaglandin D2 and its derivatives. Chem Pharm Bull 33(10) 4625-4628 (1985).

Synonyms
  • 11-deoxy-11-methylene PGD2
Formal Name 9α,​15S-​dihydroxy-​11-​methylene-​prosta-​5Z,​13E-​dien-​1-​oic acid
CAS Number 100648-29-1
Molecular Formula C21H34O4
Formula Weight 350.5
Formulation A solution in methyl acetate
Purity >98%
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(=C)​CC(O)​C1C/C=C\CCCC(=O)​O
InCHI Code
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​1S/C21H34O4/c1-3-4-7-10-17(22)​13-14-18-16(2)​15-20(23)​19(18)​11-8-5-6-9-12-21(24)​25/h5,8,13-14,17-20,22-23H,2-4,6-7,9-12,15H2,1H3,(H,24,25)​/b8-5-,14-13+/t17-,18-,19+,20-/m0/s1
InCHI Key
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ROZAFJXVUNORLT-SFIVEXQWSA-N

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11-deoxy-11-methylene Prostaglandin D2 is available in the following screening libraries:

Size Price Quantity Subtotal
1 mg $57.00 $0.00
5 mg $257.00 $0.00
10 mg $456.00 $0.00
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Pricing updated 2014-04-25. Prices are subject to change without notice.

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