39265-67-3

Usage

InChI:InChI=1/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16-,17-,19+/m0/s1

Upstream product

• 303015-41-0 (5Z,8R,9R,11S,12S,13E,15R)-11,15-bis-(tert-butyldimethylsilyloxy)-9-oxoprosta-5,13-dienoic acid 
• 303015-42-1 ethyl (5Z,8R,9R,11S,12S,13E,15R)-9-acetoxy-11,15-bis-(tert-butyldimethylsilyloxy)prosta-5,13-dienoate 
• 303015-43-2 (5Z,8R,9R,11S,12S,13E,15R)-11,15-bis-(tert-butyldimethylsilyloxy)-9-hydroxyprosta-5,13-dienoic acid 
• 214748-78-4 (Z)-7-[(1R,2S,3S,5R)-5-Acetoxy-3-hydroxy-2-((E)-(R)-3-hydroxy-oct-1-enyl)-cyclopentyl]-hept-5-enoic acid ethyl ester 

Downstream Products

• 23453-26-1 (+/-)-prostaglandin E₂ methyl ester 

Relevant academic research and scientific papers

Preparation of ent-prostaglandin E2

The enantiomeric prostaglandins, exemplified by ent-PGE2, are apparently produced in vivo by the nonenzymatic oxidation of arachidonic acid. To assess the physiological activity of ent-PGE2, it was necessary to prepare it by total sy

Racemic prostaglandins of the 2-series and analogs thereof

This invention is racemic PGE 2, racemic PGF 2 α, racemic PGF 2 β, racemic PGA 2, racemic PGB 2, analogs of those, 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, abortion, and wound healing.

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.