56687-85-5

Basic information

• Product Name: (Z)-7-[2β-[(1E,3R)-3-Hydroxy-4-(3-chlorophenoxy)-1-butenyl]-3α,5α-dihydroxycyclopentane-1α-yl]-5-heptenoic acid methyl ester
• Synonyms: (5Z,9S,11R,13E,15R)-9,11,15-Trihydroxy-16-(3-chlorophenoxy)-17,18,19,20-tetranorprosta-5,13-diene-1-oic acid methyl ester;(Z)-7-[(1R)-2β-[(E,R)-4-(3-Chlorophenoxy)-3-hydroxy-1-butenyl]-3α,5α-dihydroxycyclopentan-1α-yl]-5-heptenoic acid methyl ester;(Z)-7-[2β-[(1E,3R)-3-Hydroxy-4-(3-chlorophenoxy)-1-butenyl]-3α,5α-dihydroxycyclopentane-1α-yl]-5-heptenoic acid methyl ester;(+)-Cloprostenol methyl ester
• CAS NO: 56687-85-5
• Molecular Formula: C₂₃H₃₁ClO₆
• Molecular Weight: 438.94
• Mol File: 56687-85-5.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 585.5°C at 760 mmHg
• Flash Point: 307.9°C
• Appearance: /
• Density: 1.264g/cm³
• Vapor Pressure: 1.5E-14mmHg at 25°C
• Refractive Index: 1.596
• PKA: 13.41±0.20(Predicted)
• CAS DataBase Reference: (Z)-7-[2β-[(1E,3R)-3-Hydroxy-4-(3-chlorophenoxy)-1-butenyl]-3α,5α-dihydroxycyclopentane-1α-yl]-5-heptenoic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-7-[2β-[(1E,3R)-3-Hydroxy-4-(3-chlorophenoxy)-1-butenyl]-3α,5α-dihydroxycyclopentane-1α-yl]-5-heptenoic acid methyl ester(56687-85-5)
• EPA Substance Registry System: (Z)-7-[2β-[(1E,3R)-3-Hydroxy-4-(3-chlorophenoxy)-1-butenyl]-3α,5α-dihydroxycyclopentane-1α-yl]-5-heptenoic acid methyl ester(56687-85-5)

Safety Data

• Hazardous Substances Data: 56687-85-5(Hazardous Substances Data)

Usage

Description

(+)-Cloprostenol is a synthetic analog of prostaglandin F2α (PGF2α). It is an FP receptor agonist and a potent luteolytic agent in rats and hamsters. It is 200 times and 100 times more potent than PGF2α in terminating pregnancy in hamsters and rats, respectively, without the side effects associated with PGF2α. Cloprostenol is also used in veterinary medicine as a luteolytic agent for the induction of estrus and the treatment of reproductive disorders in cattle, swine, and horses. (+)-Cloprostenol methyl ester is a more lipid soluble form of cloprostenol, which may be more amenable for certain formulations.

InChI:InChI=1/C23H31ClO6/c1-29-23(28)10-5-3-2-4-9-19-20(22(27)14-21(19)26)12-11-17(25)15-30-18-8-6-7-16(24)13-18/h2,4,6-8,11-13,17,19-22,25-27H,3,5,9-10,14-15H2,1H3/b4-2-,12-11+/t17?,19?,20-,21?,22?/m1/s1

Upstream product

• 54276-21-0 (+)-cloprostenol 
• 74-88-4 methyl iodide 
• 52267-81-9 (3aR,4R,5R,6aS)-4-[(E)-4-(3-Chloro-phenoxy)-3-hydroxy-but-1-enyl]-5-hydroxy-hexahydro-cyclopenta[b]furan-2-one 
• 89560-44-1 (3aR,4R,5R,6aS)-4-[(E)-4-(3-Chloro-phenoxy)-3-hydroxy-but-1-enyl]-hexahydro-cyclopenta[b]furan-2,5-diol 
• 130325-32-5 Formic acid (3aR,4S,5R,6aS)-4-formyloxymethyl-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester 
• 53872-62-1 Cloprostenol 
• 62961-72-2 Corey aldehyde 
• 26054-46-6 (-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one 
• 32233-40-2 (3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one 
• 67-56-1 methanol 
• 186581-53-3 diazomethane 

Downstream Products

• 68399-12-2 16-(3-chlorophenoxy)-17,18,19,20-tetranor-2,3-trans-5,6-trans-tetradehydroprostaglandin F_1α methyl ester 
• 62559-75-5 (E)-7-[(1R,2R,3R,5S)-2-[(E)-(R)-4-(3-Chloro-phenoxy)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3,5-bis-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-2-phenylselanyl-hept-5-enoic acid methyl ester 
• 69222-86-2 (2E,5E)-7-[(1R,2R,3R,5S)-2-[(E)-(R)-4-(3-Chloro-phenoxy)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3,5-bis-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hepta-2,5-dienoic acid methyl ester 
• 69222-88-4 16-(3-chlorophenoxy)-17,18,19,20-tetranor-5,6-trans-didehydroprostaglandin F_1α methyl ester 9,11,15-tris(tetrahydropyran-2-yl ether) 
• 69222-87-3 16-(3-chlorophenoxy)-17,18,19,20-tetranor-5,6-trans-didehydroprostaglandin F_1α methyl ester 

Relevant articles and documents

Side-modified 15-deoxy-Δ12,14-prostaglandin D2, precursor of corresponding PGJ2. Synthesis from cloprostenol and anticancer activity

The title compound, a possible precursor of metabolically stable corresponding PGJ2, was obtained from cloprostenol in seven steps. The compound demonstrated cytotoxicity against the HEK 293, Hep G2 and Jurkat cell lines.

A selective method for the preparation of aliphatic methyl esters in the presence of aromatic carboxylic acids

2,2-Dimethoxypropane, methanol and a catalytic amount of HCl selectively esterify aliphatic carboxylic acids, in the presence of aromatic carboxylic acids, at room temperature and in high yields.