61949-57-3

Basic information

• Product Name: 3β-Acetoxy-7ξ-bromocholest-5-ene
• Synonyms: 3β-Acetoxy-7ξ-bromocholest-5-ene;7-Bromocholest-5-en-3β-ol acetate;7ξ-Bromo-3β-acetoxy-5(6)-cholestene;Acetic acid 7ξ-bromocholest-5-en-3β-yl ester
• CAS NO: 61949-57-3
• Molecular Formula: C₂₉H₄₇BrO₂
• Molecular Weight: 507.58628
• Mol File: 61949-57-3.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3β-Acetoxy-7ξ-bromocholest-5-ene(CAS DataBase Reference)
• NIST Chemistry Reference: 3β-Acetoxy-7ξ-bromocholest-5-ene(61949-57-3)
• EPA Substance Registry System: 3β-Acetoxy-7ξ-bromocholest-5-ene(61949-57-3)

Safety Data

• Hazardous Substances Data: 61949-57-3(Hazardous Substances Data)

Upstream product

• 57-88-5 cholesterol 
• 604-35-3 Cholesteryl acetate 
• 38774-63-9 (20S)-cholest-5-en-3β-yl acetate 

Downstream Products

• 1059-86-5 7-Dehydrocholesteryl acetate 
• 3464-60-6 cholesta-1,4,6-trien-3-one 
• 14214-69-8 cholest-4,6-diene-3-ol 
• 434-16-2 7-dehydrocholesterol 
• 94287-79-3 Carbonic acid benzyl ester (3S,8S,9S,10R,13R,14S,17R)-17-((S)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 94390-87-1 Carbonic acid benzyl ester (3S,9S,10R,13R,14R,17R)-17-((S)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 52032-64-1 Acetic acid (1S,3S,8S,9S,10R,13R,14S,17R)-3-acetoxy-17-((S)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-1-yl ester 
• 41461-10-3 Acetic acid (1S,3R,9S,10R,13R,14R,17R)-3-acetoxy-17-((S)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-1-yl ester 
• 34184-89-9 Acetic acid (3S,8S,9S,10R,13R,14S,17R)-17-((S)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 1059-86-5 cholesta-5,7-dien-3β-yl acetate 

Relevant articles and documents

PROCESS FOR PREPARATION OF 7-DEHYDROCHOLESTEROL

The invention discloses an improved cost-effective process for preparation of 7-Dehydrocholesterol of formula I with good yield and purity, comprising:a) epimerizing 7(alpha+beta) bromo protected cholesterol in presence of tetrabutyl ammonium bromide in toluene or a ketonic solvent or combinations thereof to obtain predominantly 7.alpha-bromo 3-protected cholesterol; b) Reacting 7.apha-bromo 3- protected cholesterol with substituted or unsubstituted thiophenol or its salts in presence of a liquor ammonia to obtain predominantly 7β-thiophenyl)-3-protected cholesterol; c) Oxidizing 7. beta. - thiophenyl 3-protected cholesterol in presence of Cumene hydrogen peroxide and Titanium tetraisopropoxide to obtain 7. beta. -phenyl sulfoxide 3-protected cholesterol; d) Converting 7. beta. -phenyl sulfoxide 3-protected cholesterol into 7-Dehydro 3-protected cholesterol in presence of base; e) purifying 7-Dehydro 3-protected cholesterol by suspending in a suitable organic solvent; and f) Deprotecting the 7-Dehydro 3-protected cholesterol by treating with alkali in presence of methanol to obtain 7-Dehydrocholesterol followed by purification of 7-Dehydrocholesterol from an organic solvent.

Synthesis of?oxysterols and?nitrogenous sterols with antileishmanial and?trypanocidal activities

Two sterol families have been synthesized: the first one is nitrogenous sterols containing amino, N-hydroxyimino or cyano group and the second one is oxysterols such as ketosterol and hydroxysterols. These compounds were then evaluated in vitro against Leishmania donovani promastigotes and Trypanosoma brucei brucei trypomastigotes. The most active compounds against L.?donovani promastigotes were 7β-aminomethylcholesterol and 7α,β-aminocholesterol (IC50 in a range from 1 to 3?μM, pentamidine: 2.8?μM). These compounds were active on intramacrophage amastigotes with IC50 of 1.3?μM. Such an activity justifies further in vivo antileishmanial evaluation. Against T. b. brucei, (24R,S)-24-hydroxy-24-methylcholesterol (MEC, 12.5?μM) was the most active compound from these series.

An improved synthesis of 1α-hydroxy-7-dehydrocholesterol derivatives

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