53906-54-0

Basic information

• Product Name: CLOPROSTENOL LACTONE DIOL
• Synonyms: CLOPROSTENOL LACTONE DIOL;HYDRIDE-C;(3AR,4R,5R,6aS)-4-((R,E)-4-(3-Chlorophenoxy)-3-hydroxybut-1-en-1-yl)-5-hydroxyhexahydro-2H-cyclop;(3aR,4R,5R,6aS)-4-((R,E)-4-(3-Chlorophenoxy)-3-hydroxybut-1-en-1-yl)-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one;2H-Cyclopenta[b]furan-2-one, 4-[(1E,3R)-4-(3-chlorophenoxy)-3-hydroxy-1-buten-1-yl]hexahydro-5-hydroxy-, (3aR,4R,5R,6aS)-;(3aR,4R,5R,6aS)-4-[(E,3R)-4-(3-chlorophenoxy)-3-hydroxy-but-1-enyl]-5-hydroxy-2H-Cyclopenta[b]furan-2-one;(3aR,4R,5R,6aS)-4-[(1E,3R)-4-(3-Chlorophenoxy)-3-hydroxy-1-buten-1-yl]hexahydro-5-hydroxy-2H-cyclopenta[b]furan-2-one;CL-DI
• CAS NO: 53906-54-0
• Molecular Formula: C₁₇H₁₉ClO₅
• Molecular Weight: 338.78
• Mol File: 53906-54-0.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 546.316 °C at 760 mmHg
• Flash Point: 284.202 °C
• Appearance: /
• Density: 1.423 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.648
• Storage Temp.: 2-8°C
• CAS DataBase Reference: CLOPROSTENOL LACTONE DIOL(CAS DataBase Reference)
• NIST Chemistry Reference: CLOPROSTENOL LACTONE DIOL(53906-54-0)
• EPA Substance Registry System: CLOPROSTENOL LACTONE DIOL(53906-54-0)

Safety Data

• Hazardous Substances Data: 53906-54-0(Hazardous Substances Data)

Usage

General Description

CLOPROSTENOL LACTONE DIOL is a synthetic prostaglandin analogue used in veterinary medicine for its luteolytic and uterotonic effects. It is commonly used in cattle and horses to induce estrus and regulate reproductive cycles. It works by causing the corpus luteum to regress, leading to the release of prostaglandin F2-alpha, which in turn induces luteolysis and results in the onset of estrus. In addition to its reproductive effects, CLOPROSTENOL LACTONE DIOL also has anti-inflammatory properties and has been studied for its potential use in the treatment of cystic fibrosis and other respiratory conditions. However, it is important to note that this chemical should only be used under the supervision of a veterinarian, as improper use can lead to adverse effects.

InChI:InChI=1/C17H19ClO5/c18-10-2-1-3-12(6-10)22-9-11(19)4-5-13-14-7-17(21)23-16(14)8-15(13)20/h1-6,11,13-16,19-20H,7-9H2/b5-4+/t11-,13-,14-,15-,16+/m1/s1

Upstream product

• 38754-71-1 (3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate 
• 130325-32-5 Formic acid (3aR,4S,5R,6aS)-4-formyloxymethyl-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester 
• 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 
• 53872-62-1 Cloprostenol 
• 31752-99-5 (-)-Corey lactone 5-(4-phenylbenzoate) 
• 52094-98-1 ethyl (3-chlorophenoxy)acetate 
• 108-43-0 3-monochlorophenol 
• 54324-79-7 (3aR,4R,5R,6aS)-4-((E)-4-(3-chlorophenoxy)-3-oxobut-1-enyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1′-biphenyl]-4-carboxylate 
• 40665-94-9 dimethyl 3-(3-chlorophenoxy)-2-oxopropylphosphonate 
• 53872-62-1 [3aα,4α(E),5β,6aα]-(+/-)-4-[4-(3-chlorophenoxy)-3-oxo-1-butenyl]-hexahydro-5-hydroxy-2H-cyclopenta[b]-furan-2-one 

Downstream Products

• 101915-58-6 (3aR,4R,5R,6aS)-4-[(E)-(R)-4-(3-Chloro-phenoxy)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-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 
• 109323-19-5 (1SR,5RS,6RS,7RS)-6-<(3SR)-4-(3-chlorophenoxy)-3-(1-ethoxy-ethoxy)-1(E)-butenyl>-7-(1-ethoxy-ethoxy)-2-oxabicyclo<3.3.0>octan-3-one 
• 54276-21-0 (+)-cloprostenol 
• 56687-85-5 methyl (8R,9S,11R,12S,15S)-16-(m-chlorophenoxy)-9,11,15-trihydroxy-17,18,19,20-tetranor-5Z,13E-prostadienoate 
• 206555-98-8 cloprostenol 
• 109323-20-8 (3aR,4R,5R,6aS)-4-((3R,E)-4-(3-chlorophenoxy)-3-(1-ethoxyethoxy)but-1-enyl)-5-(1-ethoxyethoxy)hexahydro-2Hcyclopenta[b]furan-2-ol 
• 79124-66-6 N-(methanesulfonyl)-16-(m-chlorophenoxy)-ω-tetranor-PGE₂-carboxamide 
• 121221-70-3 methyl 2-<(1SR, 3SR, 5RS, 6RS, 7RS)-7-tert-butyldimethylsilyloxy-6-<(3RS)-3-tert-butyldimethylsilyloxy-4-(3-chlorophenoxy)but-1(E)-en-1-yl>-2-oxabicyclo<3.3.0>oct-3-yl>acetate 
• 109323-21-9 (1SR,2RS,3RS,4RS)-3-<(3SR)-4-(3-chlorophenoxy)-3-(1-ethoxy-ethoxy)-1(E)-butenyl>-2-<3-cyano-3-dimethylamino-2(E)-propenyl>-4-(1-ethoxy-ethoxy)cyclopentanol 
• 109323-21-9 (1SR,2RS,3RS,4RS)-3-<(3SR)-4-(3-chlorophenoxy)-3-(1-ethoxy-ethoxy)-1(E)-butenyl>-2-<3-cyano-3-dimethylamino-2(Z)-propenyl>-4-(1-ethoxy-ethoxy)cyclopentanol 
• 121221-69-0 (1SR, 5RS, 6RS, 7RS)-7-tert-butyldimethylsilyloxy-6-<(3RS)-3-tert-butyldimethylsilyloxy-4-(3-chlorophenoxy)but-1(E)-en-1-yl>-2-oxabicyclo<3.3.0>octan-3ξ-ol 
• 109323-20-8 (1SR,5RS,6RS,7RS)-6-<(3SR)-4-(3-chlorophenoxy)-3-(1-ethoxy-ethoxy)-1(E)-butenyl>-7-(1-ethoxy-ethoxy)-2-oxabicyclo<3.3.0>octan-3ξ-ol 

Relevant articles and documents

An improved and efficient process for the preparation of (+)-cloprostenol

Abstract An improved and efficient synthesis of (+)-cloprostenol has been accomplished in nine steps and 26% overall yield from commercially available (-)-Corey lactone 4-phenylbenzoate alcohol 1. The present route avoids tedious purifications and require

PROSTANOIDS. XXVII. SOME ASPECTS OF CHEMO- AND STEREOSELECTIVE REDUCTION OF 7α-HYDROXY-6β-(3-OXO-4-m-CHLOROPHENOXY-1E-BUTENYL)-2-OXABICYCLOOCTAN-3-ONE

The chemoselective reduction of 7α-hydroxy-6β-(3-oxo-4-m-chlorophenoxy-1E-butenyl)-2-oxabicyclooctan-3-one with respect to the oxo group was studied by means of readily obtainable reagents based on boron and aluminum.The optimum stereoselectivity of reduction was obtained with the use of diisobutylaluminum 2,6-di-tert-butyl-4-methylphenoxide in methylene chloride at -78 deg C.