27415-25-4

Usage

Uses

Used in Pharmaceutical and Biomedical Research:
8-ISO PROSTAGLANDIN E2 is used as a biomarker for oxidative stress and lipid peroxidation in various research studies. Its presence in biological samples indicates the level of oxidative damage, which can be crucial in understanding the pathophysiology of numerous diseases and conditions.
Used in Ophthalmology:
In the field of ophthalmology, 8-ISO PROSTAGLANDIN E2 is used as an inhibitor of endogenous amino acid neurotransmitter levels in bovine retina. This application helps researchers study the effects of oxidative stress on the retina and develop potential therapeutic strategies for retinal diseases.
Used in Analytical Chemistry:
8-ISO PROSTAGLANDIN E2 can be used as a reference compound in the development and validation of analytical methods for the detection and quantification of prostaglandins and other related bioactive molecules. This application is essential for ensuring the accuracy and reliability of analytical techniques in various research and diagnostic settings.
Used in Toxicology:
8-ISO PROSTAGLANDIN E2 is used as a biomarker to assess the toxic effects of various environmental and industrial pollutants on living organisms. By measuring the levels of 8-ISO PROSTAGLANDIN E2 in biological samples, researchers can evaluate the extent of oxidative stress and potential damage caused by exposure to toxic substances.
Used in Nutritional Science:
In the field of nutritional science, 8-ISO PROSTAGLANDIN E2 can be used to study the effects of dietary components on oxidative stress and inflammation. This application helps researchers understand the role of specific nutrients in promoting health and preventing disease.
Used in Cosmetics Industry:
8-ISO PROSTAGLANDIN E2 can be used in the development of cosmetic products that target oxidative stress and inflammation in the skin. By incorporating this molecule or its derivatives into skincare formulations, the cosmetics industry can offer products that help protect the skin from environmental stressors and promote a healthier, more youthful appearance.

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

• 489427-38-5 11,15-O-bis(tert-butyldimethylsilyl)PGE₂ methyl ester 
• 82542-42-5 Methyl (Z)-7-<(3R)-3-<(tert-Butyldimethylsilyl)oxy>-5-oxo-1-cyclopentenyl>-5-heptenoate 
• 98497-60-0 methyl 7-<3(R)-(acetyloxy)-5-oxo-1-cyclopenten-1-yl>-5(Z)-heptenoate 
• 42541-96-8 Methyl (Z)-7-<(3R)-3-Hydroxy-5-oxo-1-cyclopentenyl>-5-heptenoate 
• 31753-18-1 15-E_2t-isoprostane methyl ester 
• 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 
• 303015-41-0 (5Z,8R,9R,11S,12S,13E,15R)-11,15-bis-(tert-butyldimethylsilyloxy)-9-oxoprosta-5,13-dienoic acid 

Downstream Products

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

Relevant academic research and scientific papers

Improved synthesis of (E)-12-nitrooctadec-12-enoic acid, a potent PPARγ activator. development of a "buffer-Free" enzymatic method for hydrolysis of methyl esters

Endogenous nitro-fatty acids, acting as partial agonist of PPARγ, are able to lower the insulin and glucose levels without the side effects associated with common antidiabetic drugs. (E)-12-Nitrooctadec-12-enoic acid, a potent activator of this peroxisome receptor, was synthesized in a very efficient sequence via a Henry-retro-Claisen ring fragmentation, followed by a novel enzymatic cleavage of methyl esters. The latter method was then applied in the last step of the synthesis of a few labile natural products, such as prostaglandins, isoprostanes, and phytoprostanes.

Total synthesis of E1 and E2 isoprostanes by diastereoselective protonation

A short total synthesis of the E-type isoprostanes has been achieved using a two-component coupling process combined with a diastereoselective protonation under reagent control. Mild cleavage of the silyl protective groups with cat. BiBr3 or HF/Py followed by enzymatic hydrolysis of the methyl ester afforded the free E-type isoprostanes.

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.