23453-26-1

Basic information

• Product Name: (+/-)-prostaglandin E₂ methyl ester
• CAS NO: 23453-26-1
• Molecular Weight: 366.498
• Mol File: 23453-26-1.mol

Chemical Properties

• CAS DataBase Reference: (+/-)-prostaglandin E₂ methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-prostaglandin E₂ methyl ester(23453-26-1)
• EPA Substance Registry System: (+/-)-prostaglandin E₂ methyl ester(23453-26-1)

Safety Data

• Hazardous Substances Data: 23453-26-1(Hazardous Substances Data)

Upstream product

• 63942-75-6 PGH₂ methyl ester 
• 186581-53-3 diazomethane 
• 363-24-6 (+/-)-prostaglandin E₂ 
• 66602-10-6 methyl (5Z,13E)-11α,15-bis(dimethyl-t-butylsilyloxy)-9-oxoprosta-5,13-dienoate 
• 66602-10-6 methyl (5Z,13E,15S)-11α,15-bis(dimethyl-t-butylsilyloxy)-9-oxoprosta-5,13-dienoate 
• 66602-11-7 methyl (5Z,13E)-11α,15-bis(dimethyl-t-butylsilyloxy)-9α-hydroxyprosta-5,13-dienoate 
• 66602-11-7 methyl (5Z,15S)-11α,15-bis(dimethyl-t-butylsilyloxy)-9α-hydroxyprosta-5,13-dienoate 
• 128683-91-0 1-[1-((1E,3E)-4-Iodo-buta-1,3-dienyl)-hexyloxymethyl]-4-methoxy-benzene 
• 128683-93-2 Acetic acid (3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-3-[(E)-3-(4-methoxy-benzyloxy)-oct-1-enyl]-cyclopent-1-enyl ester 
• 128683-92-1 Acetic acid (1R,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-[(1E,3E)-5-(4-methoxy-benzyloxy)-deca-1,3-dienyl]-cyclopropyl ester 
• 128683-95-4 (Z)-7-{(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-3-(4-methoxy-benzyloxy)-oct-1-enyl]-5-oxo-cyclopentyl}-hept-5-enoic acid methyl ester 
• 137696-44-7 (5Z,11R,12β,13E,15S)-11-<(tert-Butyldiphenylsilyl)oxy>-9-oxoprosta-5,13-dien-1-oic acid methylester 
• 25152-84-5 trans,trans-2,4-decadienal 
• 137696-31-2 3(R)-Hydroxy-(E,E)-4,6-dodecadienoic acid 

Downstream Products

• 31753-19-2 (Z)-7-[(1S,2R)-2-((E)-(R)-3-Hydroxy-oct-1-enyl)-5-oxo-cyclopent-3-enyl]-hept-5-enoic acid methyl ester 

Relevant articles and documents

Enantioselective Rh-Mediated Synthesis of (-)-PGE2 Methyl Ester

Intramolecular Rh(II) carboxylate catalyzed cyclization of an α-diazo β-methylene ketone to form a fused cyclopropane is shown to compete efficiently with β-hydride elimination, so long as a catalyst derived from an electron-donating carboxylate is used.C

PALLADIUM(0) CATALYZED REACTIONS OF 1,4-EPIPEROXIDES

The Pd(PPh3)4 catalyzed reaction of 2,3-saturated and 2,3-unsaturated 1,4-epiperoxides proceeds by courses markedly different from those of the previously reported transition metal catalyses.The Pd(0)-promoted reaction of 2,3-saturated epiperoxides gives the corresponding 4-hydroxy ketones and 1,4-diols as the major products.From 2,3-dedihydroepiperoxides are formed the corresponding 4-hydroxy enones, syn-1,2;3,4-diepoxides, and 1,4-diols.The results are interpreted in terms of competing Pd(0)/Pd(II) exchange mechanisms.Exposure of prostaglandin (PG) H2 methyl esterto Pd(PPh3)4 produces a mixture of methyl esters of PGD2, PGE2, PGF2α, and (5Z,8E,10E,12S)-12-hydroxy-5,8,10-heptadecatrienoic acid.

Total Synthesis of (+/-)-Prostaglandin E2 Methyl Ester from exo-2-Bromo-endo-3-hydroxybicycloheptan-6-one using Dimethyl-t-butylsilyl Protected Intermediates

Peracetic acid oxidation at -78 deg C of the dihydroxybicyclohepten-6-one (23) afforded the dihydroxylactone (24) which was protected as its bisdimethyl-t-butylsilyl ether (26) and reduced to the corresponding lactol (27).A Wittig reaction on (27), carried out in benzene with a short reaction time, gave mainly the required 11α-silyl ether (28) together with a trace of the 9α-silyl ether (29) which results from 1,5-migration of the silyl group.Oxidation of (28) followed by quantitative deprotection using aqueous HF in acetonitrile afforded (+/-)-PGE2 methyl ester (20).This short stereo- and regioselective total synthesis proceeds in an overall yield of 10percent starting from cyclopentadiene.

8β,12α,15β-PGF2 β Compounds

This invention is a group of 8-beta, 12-alpha-PG2 (prostaglandin-type) analogs having variable chain length, or methyl or phenyl substitution in the hydroxy-substituted side-chain, and processes for making them. These compounds are useful for a variety of pharmacological purposes, including anti-ulcer, inhibition of platelet aggregation, increase of nasal patency, and labor inducement at term.

Enzymatic preparation and purification of prostaglandin E2.

An enzymatic system has been developed for the production of prostaglandin E(2) (PGE(2)) from arachidonic acid by extracts of sheep seminal vesicular glands. The presence of glutathione insures high yields. A new procedure for the purification of PGE(2) was also developed, based on the dialysis of the biosynthesized product at pH 8 and extraction of the dialysate at pH 3 with chloroform. This procedure routinely gives yields of PGE(2) of 25-37% (from arachidonic acid) with a purity of 90-100%. Additional analytical proof of the identity of PGE(2) was provided by physicochemical characteristics of the crystalline thiosemicarbazide derivative, which can be readily prepared under mild conditions.