20-ethyl Prostaglandin E2

Cayman Chemical Item Number 14940

20-ethyl PGE2 (CAS 37492-24-3)

20-ethyl Prostaglandin E2 (CAS 37492-24-3)

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Description

20-ethyl Prostaglandin E2 (20-ethyl PGE2) is an analog of PGE2 in which the ω-chain has been extended by the addition of two methylene carbon atoms. The only well studied prostaglandin analog with this structural feature is unoprostone, an F-series prostaglandin that is clinically approved as a glaucoma medication.1 Unoprostone also contains lower side chain modifications (13,14-dihydro-15-keto) which severely limit its affinity for FP receptors, contributing to its lack of potency as a medication. 20-ethyl PGE2 retains the natural 15(S) allylic hydroxyl in the lower side chain, which may improve its potency relative to unoprostone. However, ligand binding assays of this analog with respect to EP or other prostanoid receptors have not been published. E-type prostaglandins have been widely reported to have inflammatory,2 cytoprotective,3 and a variety of other effects.4

1 Haria, M., and Spencer, C.M. Unoprostone (isopropyl unoprostone). Drugs Aging 9 213-218 (1996).

2 Matsumoto, H., Naraba, H., Murakami, M., et al. Concordant induction of prostaglandin E2 synthase with cyclooxygenase-2 leads to preferred production of prostaglandin E2 over thromboxane and prostaglandin D2 in lipopolysaccharide-stimulated rat peritoneal macrophages. Biochem Biophys Res Commun 230 110-114 (1997).

3 Karim, S.M.M., Carter, D.C., Bhana, D., et al. Effect of orally administered prostaglandin E2 and its 15-methyl analogues on gastric secretion. Br Med J 1 143-146 (1973).

4 Jackson, G.M., Sharp, H.T., and Varner, M.W. Cervical ripening before induction of labor: A randomized trial of prostaglandin E2 gel versus low-dose oxytocin. Am J Obstet Gynecol 171 1092-1096 (1994).

Synonyms
  • 20-ethyl PGE2
Formal Name 9-​oxo-​11α,​15S-​dihydroxy-​20a,​20b-​dihomoprosta-​5Z,​13E-​dien-​1-​oic acid
CAS Number 37492-24-3
Molecular Formula C22H36O5
Formula Weight 380.5
Formulation A solution in methyl acetate
Purity >97%
Stability 1 year
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES
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CCCCCCC[C@H]​(O)​/C=C/[C@H]​([C@H]​1C/C=C\CCCC(O)​=O)​[C@H]​(O)​CC1=O
InCHI Code
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​1S/C22H36O5/c1-2-3-4-5-8-11-17(23)​14-15-19-18(20(24)​16-21(19)​25)​12-9-6-7-10-13-22(26)​27/h6,9,14-15,17-19,21,23,25H,2-5,7-8,10-13,16H2,1H3,(H,26,27)​/b9-6-,15-14+/t17-,18+,19+,21+/m0/s1
InCHI Key
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NXMMZTNQIJBMBC-QKIVIXBWSA-N

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20-ethyl Prostaglandin E2 is available in the following screening libraries:

Size Price Quantity Subtotal
1 mg $51.00 $0.00
5 mg $230.00 $0.00
10 mg $408.00 $0.00
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Cart Total $0.00

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Pricing updated 2014-04-19. Prices are subject to change without notice.

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Cayman Chemical Company regularly evaluates our shipping methods to ensure product stability is maintained and our corporate environmental impact is minimized. Products selected for review are evaluated and shipping methods are certified by our Scientists. While occasionally our method of shipping a product may change, rest assured the shipping conditions on all Cayman Chemical products have been reviewed and validated.

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