3434-33-1

Basic information

• Product Name: PROSTAGLANDIN E1 METHYL ESTER
• Synonyms: PROSTAGLANDIN E1 METHYL ESTER;(13E,15S)-11α,15-Dihydroxy-9-oxoprost-13-en-1-oic acid methyl ester;7-[(1R,2R,3R)-3-Hydroxy-2-[(1E,3S)-3-hydroxy-1-octenyl]-5-oxocyclopentyl]heptanoic acid methyl ester
• CAS NO: 3434-33-1
• Molecular Formula: C₂₁H₃₆O₅
• Molecular Weight: 368.51
• Mol File: 3434-33-1.mol

Chemical Properties

• Appearance: /
• Storage Temp.: −20°C
• CAS DataBase Reference: PROSTAGLANDIN E1 METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: PROSTAGLANDIN E1 METHYL ESTER(3434-33-1)
• EPA Substance Registry System: PROSTAGLANDIN E1 METHYL ESTER(3434-33-1)

Safety Data

• Hazard Codes: F,Xn
• Statements: 11-20/21/22-36/37/38
• Safety Statements: 16-26-36/37/39
• Hazardous Substances Data: 3434-33-1(Hazardous Substances Data)

Upstream product

• 60934-42-1 7-{5-oxo-3-[(tetrahydro-2H-pyran-2-yl)oxy]cyclopent-1-en-1-yl}heptanoic acid methyl ester 
• 42542-00-7 (S)-3-(1-ethoxy-ethoxy)-1t-iodo-oct-1-ene 
• 86982-75-4 11,15-O-bis(tert-butyldimethylsilyl)PGE₁ methyl ester 
• 39178-64-8 (E)-1-iodo-1-octen-3-one 
• 41138-61-8 (4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone 
• 35376-00-2 methyl 7-oxoheptanoate 
• 50438-50-1 1-methoxycycloheptene 
• 72522-67-9 (1E)-iodo-(3S)-(tetrahydro-2H-pyran-2-yloxy)-1-octene 
• 96038-40-3 (E,3S)-3-(tetrahydropyran-2-yloxy)-1-octenyllithium 
• 85366-10-5 (7E)-7,8-didehydro-11,15-bis-O-(tetrahydropyran-2-yl)PGE₁ methyl ester 
• 117179-96-1 7-hydroxy-11,15-bis-O-(tetrahydropyran-2-yl)PGE₁ methyl ester 
• 32556-71-1 1-octyn-3-ol 
• 60176-77-4 (1S,4R)-4-hydroxy-2-cyclopentenyl acetate 
• 61305-35-9 (R)-4-((tert-butyldimethylsilyl)oxy)cyclopent-2-enone 

Downstream Products

• 745-65-3 ALPROSTADIL 

Relevant articles and documents

Pot economy in the synthesis of prostaglandin A1 and E 1 methyl esters

Pot luck: Prostaglandins regulate a broad range of physiological processes and some of their derivatives are used as effective drugs, but previously their preparation has required many steps. The title compounds were efficiently synthesized in a small number of synthetic steps by using a recently developed organocatalyst and practical, one-pot operations involving several successive reactions.

A SHORT SYNTHESIS OF (-)-PROSTAGLANDIN E1

(-)-Prostaglandin E1 has been prepared from (R)-4-t-butyldimethylsiloxy-2-cyclopentenone by using as a key operation the tandem organocopper conjugate addition/nitroolefin Michael trapping of the resulting enolate intermediate.

USE OF PROSTAGLANDIN E1 METHYL ESTER IN PREPARING VASODILATOR DRUG

Provided in the present invention is a use of prostaglandin E1 methyl ester in preparing a vasodilator drug. The structural formula of the prostaglandin E1 methyl ester is represented by formula (I) The vasodilator drug is a drug used to treat the following diseases: a microcirculatory disorder, coronary heart disease, angina, heart failure, pulmonary heart disease, cerebral infarction, amniotic fluid embolism, or scleroderma.

A prostaglandin E1 methyl ester freeze dried preparation for injection and its preparation and use (by machine translation)

The present invention provides a prostaglandin E1 methyl ester freeze dried preparation for injection and preparation and application. The freeze-dried preparation comprises the following parts by weight ingredient: prostaglandin E1 methyl ester 0.1 - 10 parts, oil for injection 500 - 4000 parts, emulsifier 500 - 2000 parts, emulsifier 0 - 10 parts, lyophilized vaccine 5000 - 50000 parts, and glycerin 200 - 1500 parts. The invention prostaglandin E1 methyl ester freeze-dried agent has stimulate the blood vessel small, good stability of the medicine, and compared with similar prostaglandin E1 product just excellent pharmaceutical activity and the therapeutic effect. (by machine translation)

One-Step conversion to a disubstituted cyclopentenone from 2-Deoxy-D-Glucose and application to synthesis of prostaglandin e1 methyl ester

We have developed a facile one-step conversion of 2-deoxy-D-glucose to form a disubstituted cyclopentenone through catalyst-free hydrothermal reaction under mild conditions. The use of 2-deoxy-D-glucose in one-pot conversion is to provide the formation of a carbon five-membered ring instead of the common biomass-derived furans such as furfural, 5-HMF, etc. The cyclopentenone has a potential to be a building block for the preparation of chemical products. As one example, we successfully demonstrated the synthesis of prostaglandin E1 methyl ester.

Nitrostated and nitrosylated prostaglandins, compositions and methods of use

The present invention describes novel nitrosated and/or nitrosylated prostaglandins, and novel compositions comprising at least one nitrosated and/or nitrosylated prostaglandin, and, optionally, at least one compound that donates, transfers or releases nitric oxide, elevates endogenous levels of endothelium-derived relaxing factor, stimulates endogenous synthesis of nitric oxide or is a substrate for nitric oxide synthase, and/or at least one vasoactive agent. The present invention also provides novel compositions comprising at least one prostaglandin and at least one S-nitrosothiol compound, and, optionally, at least one vasoactive agent. The prostaglandin is preferably a prostaglandin E1 compound, more preferably alprostadil, and the S-nitrosothiol compound is preferably S-nitrosoglutathione. The present invention also provides methods for treating or preventing sexual dysfunctions in males and females, for enhancing sexual responses in males and females, and for treating or preventing cerebrovascular disorders, cardiovascular disorders, benign prostatic hyperplasia (BPH), glaucoma, peptic ulcers or for inducing abortions. The compounds and/or compositions of the present invention can also be provided in the form of a pharmaceutical kit.

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.

Catalytic enantioselective synthesis of (-)-prostaglandin E1 methyl ester based on a tandem 1,4-addition-aldol reaction

Catalytic enantioselective 1,4-additions and tandem 1,4-addition-aldol reactions of dialkylzinc reagents to cyclopentene-3,5-dione monoacetals in the presence of an in situ generated Cu(OTf)2/chiral phosphoramidite catalyst result in highly functionalized cyclopentane building blocks with ee's up to 97%. A new synthesis of cyclopentene-3,5-dione monoacetals is presented as well as its use in a tandem 1,4-addition-aldol protocol for the catalytic asymmetric total synthesis of (-)-PGE1 methyl ester. This synthesis represents a new approach to this class of natural products. By using only 3 mol % of an enantiomerically pure catalyst in the key step, the absolute configurations at three stereocenters of the basic structure of the PGE1 are established at once.

An efficient asymmetric synthesis of prostaglandin E1

An asymmetric total synthesis of Prostaglandin E1 (5) has been achieved in a two-component coupling process. The chiral hydroxycyclopentenone 6 was readily available from furan with 96% ee. The key reaction step was a kinetic enzymatic resolution followed by an in situ inversion. A catalytic asymmetric reduction of the γ-iodo vinyl ketone 19 with the Corey CBS catalyst gave the ω-side chain 7 with >96% ee. Conjugate addition using the reaction with dilithiocyanocuprate followed by mild cleavage of the silyl protective groups and enzymatic hydrolysis of the methyl ester 22 gave (-)-PGE1 5 in high yield.