130209-77-7

Basic information

• Product Name: 15-keto-17-phenyl-18,19,20-trinorprostaglandin F2 alpha-1-isopropyl ester
• Synonyms: 15-keto-17-phenyl-18,19,20-trinorprostaglandin F2 alpha-1-isopropyl ester
• CAS NO: 130209-77-7
• Molecular Formula: C₂₆H₃₆O₅
• Molecular Weight: 428.56104
• Mol File: 130209-77-7.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 569.8°Cat760mmHg
• Flash Point: 184.4°C
• Appearance: /
• Density: 1.138g/cm³
• Vapor Pressure: 8.04E-14mmHg at 25°C
• Refractive Index: 1.572
• CAS DataBase Reference: 15-keto-17-phenyl-18,19,20-trinorprostaglandin F2 alpha-1-isopropyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 15-keto-17-phenyl-18,19,20-trinorprostaglandin F2 alpha-1-isopropyl ester(130209-77-7)
• EPA Substance Registry System: 15-keto-17-phenyl-18,19,20-trinorprostaglandin F2 alpha-1-isopropyl ester(130209-77-7)

Safety Data

• Hazardous Substances Data: 130209-77-7(Hazardous Substances Data)

Usage

General Description

15-keto-17-phenyl-18,19,20-trinorprostaglandin F2 alpha-1-isopropyl ester is a synthetic chemical compound that is derived from the natural prostaglandin F2 alpha. It is commonly used in research and pharmaceutical applications as a potent and selective agonist of the prostaglandin F receptor. 15-keto-17-phenyl-18,19,20-trinorprostaglandin F2 alpha-1-isopropyl ester has been studied for its potential therapeutic effects in conditions such as glaucoma, asthma, and labor induction. Its 1-isopropyl ester structure provides enhanced stability and improved pharmacokinetic properties, making it a valuable tool for studying the biological functions and signaling pathways of prostaglandin receptors. Additionally, its phenyl substitution at the 17th carbon position may confer specific binding interactions and modulate the compound's pharmacological activity.

InChI:InChI=1/C26H36O5/c1-19(2)31-26(30)13-9-4-3-8-12-22-23(25(29)18-24(22)28)17-16-21(27)15-14-20-10-6-5-7-11-20/h3,5-8,10-11,16-17,19,22-25,28-29H,4,9,12-15,18H2,1-2H3/b8-3-,17-16+/t22-,23-,24+,25-/m1/s1

Upstream product

• 38344-08-0 (5Z)-bimatoprost acid 
• 41162-19-0 dimethyl(2-oxo-4-phenylbutyl)phosphonate 
• 177616-22-7 (Z)-7-((1R,2S,3R,5S)-3,5-Dihydroxy-2-hydroxymethyl-cyclopentyl)-hept-5-enoic acid isopropyl ester 
• 130209-76-6 15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F_2α isopropyl ester 

Downstream Products

• 177768-49-9 (Z)-7-{(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(2R,3R)-3-((R)-1-hydroxy-3-phenyl-propyl)-oxiranyl]-cyclopentyl}-hept-5-enoic acid isopropyl ester 
• 177768-48-8 (Z)-7-{(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(2S,3S)-3-((R)-1-hydroxy-3-phenyl-propyl)-oxiranyl]-cyclopentyl}-hept-5-enoic acid isopropyl ester 
• 130273-87-9 15β-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F_2α isopropyl ester 
• 130209-76-6 15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F_2α isopropyl ester 

Relevant articles and documents

Regio- and stereoselective reactions of 17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester

Novel prostaglandin F2α derivatives, functionalized at C13 and C14, have been prepared. 17-Phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester [(15S)-1] and its epimer [(15A)-1] were stereoselectively epoxidized, using Sharpless conditions, to produce each of the four diastereomeric epoxides (15S)-2, (15S)-3, (15R)-2, and (15R)-3. Treatment of the four epoxides with LiOH stereospecifically-produced the pentahydroxy substituted analogues 12 and 13. Alternatively, epoxides 2 and 3 were allowed to react with thiophenolate ion. The attack of the sulfur nucleophile on the epoxide occurred at either C13 or C14 depending on the stereochemistry of the epoxide and of C15.