31753-17-0

Basic information

• Product Name: PROSTAGLANDINS E2 METHYL ESTER
• Synonyms: 9-OXO-11ALPHA,15S-DIHYDROXY-PROSTA-5Z,13E-DIEN-1-OIC ACID, METHYL ESTER;7-(3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl)-5-heptenoicacimeth;pge2methylester;ylester,stereoisomer;PROSTAGLANDIN E2 METHYL ESTER;PROSTAGLANDINS E2 METHYL ESTER;(5Z)-7-[(1R)-2β-[(1E,3S)-3-Hydroxy-1-octenyl]-3α-hydroxy-5-oxocyclopentane-1α-yl]-5-heptenoic acid methyl ester;(5Z,13E,15S)-11α,15-Dihydroxy-9-oxo-5,13-prostadiene-1-oic acid methyl ester
• CAS NO: 31753-17-0
• Molecular Formula: C₂₁H₃₄O₅
• Molecular Weight: 366.49
• Mol File: 31753-17-0.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 492.5°C at 760 mmHg
• Flash Point: 162.1°C
• Appearance: /
• Density: 1.103g/cm³
• Vapor Pressure: 9.11E-12mmHg at 25°C
• Refractive Index: 1.539
• Storage Temp.: −20°C
• CAS DataBase Reference: PROSTAGLANDINS E2 METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: PROSTAGLANDINS E2 METHYL ESTER(31753-17-0)
• EPA Substance Registry System: PROSTAGLANDINS E2 METHYL ESTER(31753-17-0)

Safety Data

• Hazard Codes: F,Xn
• Statements: 11-20/21/22-36/37/38
• Safety Statements: 16-26-36
• RIDADR: UN 1231 3/PG 2
• WGK Germany: 3
• Hazardous Substances Data: 31753-17-0(Hazardous Substances Data)

Usage

Description

Prostaglandin E2 methyl ester (PGE2 methyl ester) is an analog of PGE2 with enhanced lipid solubility. PGE2 is one of the primary cyclooxygenase products of arachidonic acid and one of the most widely investigated PGs. Its activity influences inflammation, fertility and parturition, gastric mucosal integrity, and immune modulation. The effects of PGE2 are transduced by at least four distinct receptors designated EP1, EP2, EP3, and EP4. Affinity constants (Kd) values of PGE2 for these receptors range from 1-10 nM depending on the receptor subtype and tissue.

InChI:InChI=1/C21H34O5/c1-3-4-7-10-16(22)13-14-18-17(19(23)15-20(18)24)11-8-5-6-9-12-21(25)26-2/h5,8,13-14,16-18,20,22,24H,3-4,6-7,9-12,15H2,1-2H3/b8-5+,14-13+/t16-,17+,18+,20+/m0/s1

Upstream product

• 137696-30-1 <1S-(exo,exo)>-4,7,7-Trimethyl-3-(1-naphthyl)bicyclo<2.2.1>heptan-2-yl 3(R)-hydroxy-(E,E)-4,6-dodecadienoate 
• 31703-58-9 2-<(7-Iodo-5-heptynyl)oxy>-2H-tetrahydropyran 
• 63942-75-6 PGH₂ methyl ester 
• 66602-10-6 11,15-bis(o-tert-butyldimethylsilyl) PGE₂ methyl ester 
• 85453-69-6 Methyl (5Z,13E,8R,11R,12R,15S)-11,15-Bis(tert-butyldimethylsiloxy)-9-(anti-oximino)-5,13-prostadienoate 
• 72522-67-9 (1E)-iodo-(3S)-(tetrahydro-2H-pyran-2-yloxy)-1-octene 
• 42542-01-8 (Z)-7-[(R)-5-Oxo-3-(tetrahydro-pyran-2-yloxy)-cyclopent-1-enyl]-hept-5-enoic acid methyl ester 
• 42542-00-7 (S)-3-(1-ethoxy-ethoxy)-1t-iodo-oct-1-ene 
• 103904-98-9 methyl (5Z)-7-<6-<(1E)-3-<(tert-butyldimethylsilyl)oxy>-1-octenyl>-2,2-dimethyl-4-oxo-3aβ,5β,6α,6aβ-tetrahydro-4H-cyclopenta-1,3-dioxol-5-yl>-5-heptenoate 
• 103904-95-6 meso-4β,6-diacetoxy-2,2-dimethyl-3αβ,5,6α,6αβ-tetrahydro-4H-cyclopenta-1,3-dioxole 
• 115420-61-6 3α,5α-diacetoxy-1β,2β-cyclopentanediol 
• 542-92-7 cyclopenta-1,3-diene 
• 64244-45-7 methyl (Z)-7-hydroxy-5-heptenoate 
• 40269-54-3 (+/-)-2,2-dimethyl-3αβ,6αβ-dihydro-4H-cyclopenta-1,3-dioxol-4-one 

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 
• 81755-82-0 (-)-11α-acetylthio-11-deoxy-11α-homoprostaglandin E₂ acetate methyl ester 
• 89616-99-9 (Z)-7-[(1R,2R,4R)-2-((E)-(S)-3-Acetoxy-oct-1-enyl)-4-acetylsulfanyl-6-oxo-cyclohexyl]-hept-5-enoic acid methyl ester 
• 89617-00-5 (+)-11α-acetylthio-11-deoxy-11α-homoprostaglandin F_2β 15-acetate methyl ester 
• 89560-32-7 (Z)-7-[(1R,2R,4S,6S)-2-((E)-(S)-3-Acetoxy-oct-1-enyl)-4-acetylsulfanyl-6-hydroxy-cyclohexyl]-hept-5-enoic acid methyl ester 
• 89617-02-7 9,11-epithio-11,12-methano-thromboxane A₂ 
• 89560-27-0 (3R,4R)-4-((E)-(S)-3-Acetoxy-oct-1-enyl)-3-((Z)-6-methoxycarbonyl-hex-2-enyl)-2-oxo-1-phenylselanyl-cyclohexanecarboxylic acid ethyl ester 
• 89560-31-6 (3R,4R)-4-((E)-(S)-3-Acetoxy-oct-1-enyl)-3-((Z)-6-methoxycarbonyl-hex-2-enyl)-2-oxo-6-propylsulfanyl-cyclohexanecarboxylic acid ethyl ester 
• 81755-83-1 (Z)-7-[(1R,2R,4S,6R)-2-((E)-(S)-3-Acetoxy-oct-1-enyl)-4-acetylsulfanyl-6-methanesulfonyloxy-cyclohexyl]-hept-5-enoic acid methyl ester 
• 81755-80-8 (3R,4R)-4-((E)-(S)-3-Acetoxy-oct-1-enyl)-3-((Z)-6-methoxycarbonyl-hex-2-enyl)-2-oxo-cyclohexanecarboxylic acid ethyl ester 
• 89560-26-9 (3R,4R)-4-((E)-(S)-3-Acetoxy-oct-1-enyl)-2-hydroxy-3-((Z)-6-methoxycarbonyl-hex-2-enyl)-cyclohexanecarboxylic acid ethyl ester 
• 89560-28-1 (4R,5R)-4-((E)-(S)-3-Acetoxy-oct-1-enyl)-5-((Z)-6-methoxycarbonyl-hex-2-enyl)-6-oxo-cyclohex-1-enecarboxylic acid ethyl ester 
• 89560-25-8 (Z)-7-[(1R,2R)-2-((E)-(S)-3-Acetoxy-oct-1-enyl)-6-oxo-cyclohexyl]-hept-5-enoic acid methyl ester 
• 89560-24-7 (Z)-7-[(1S,2S)-2-((E)-(S)-3-Acetoxy-oct-1-enyl)-5-oxo-cyclohexyl]-hept-5-enoic acid methyl ester 

Relevant articles and documents

Synthesis of prostaglandin E2 methyl ester on a soluble-polymer support for the construction of prostanoid libraries

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Novel and flexible entries into prostaglandins and analogues based on ring closing alkyne metathesis or alkyne cross metathesis

The suitably functionalized cyclopentanone derivatives 12, 13, 19, and 37 serve as common precursors for the synthesis of various prostaglandins, prostaglandin-1,15-lactones, and unnatural analogues thereof. All of them contain a 2-butynyl entity which is

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