2953-38-0

Basic information

• Product Name: (3alpha)-5,6-epoxycholestan-3-ol
• CAS NO: 2953-38-0
• Molecular Formula: C₂₇H₄₆O₂
• Molecular Weight: 402.6529
• Mol File: 2953-38-0.mol
• Article Data: 44

Chemical Properties

• Boiling Point: 497.7°C at 760 mmHg
• Flash Point: 200.9°C
• Density: 1.04g/cm³
• Vapor Pressure: 5.43E-12mmHg at 25°C
• Refractive Index: 1.533
• CAS DataBase Reference: (3alpha)-5,6-epoxycholestan-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (3alpha)-5,6-epoxycholestan-3-ol(2953-38-0)
• EPA Substance Registry System: (3alpha)-5,6-epoxycholestan-3-ol(2953-38-0)

Safety Data

• Hazardous Substances Data: 2953-38-0(Hazardous Substances Data)

Usage

General Description

(3alpha)-5,6-epoxycholestan-3-ol, also known as cholestane-5,6-epoxide, is a sterol derivative that is formed through the epoxidation of cholesterol. It is a key intermediate in the biosynthesis of bile acids and steroid hormones. Cholestane-5,6-epoxide has been identified as a potential toxicant and has been implicated in the development of atherosclerosis. It has also been investigated for its potential anti-tumor and anti-inflammatory properties. The compound has a unique structure that makes it valuable in the study of cholesterol metabolism and as a potential target for drug development.

Upstream product

• 93-59-4 Perbenzoic acid 
• 67-66-3 chloroform 
• 57-88-5 cholesterol 
• 57-88-5 cholesterol 
• 53357-27-0 5-bromo-5α-cholestane-3β,6β-diol diacetate 
• 2572-55-6 5α-cholestane-3β,5α,6β-triyl triacetate 
• 75-65-0 tert-butyl alcohol 
• 108-05-4 vinyl acetate 
• 55700-78-2 (6aS,6bS,9R,9aR,11aS,11bR)-9a,11b-dimethyl-9-((R)-6-methylheptan-2-yl)hexadecahydrocyclopenta[1,2]phenanthro[8a,9-b]oxiren-3-ol 
• 4447-87-4 (3S,5R,6R,8S,9S,10R,13R,14S,17R)-5-fluoro-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthrene-3,6-diol 
• 604-35-3 Cholesteryl acetate 
• 6557-19-3 5β,6β-epoxy-cholestan-3β-ol benzoate 
• 604-32-0 cholesteryl benzoate 
• 95841-69-3 5β,6β-epoxy-7α-bromocholestan-3β-ol benzoate 

Downstream Products

• 1260-20-4 6α-phenyl-5α-cholestanediol-(3β,6β) 
• 6557-19-3 5β,6β-epoxy-cholestan-3β-ol benzoate 
• 1253-84-5 cholestanetriol 
• 28925-98-6 3β-acetoxy-6-phenyl-cholest-5-ene 
• 103390-43-8 acetic acid-(6β-hydroxy-6α-phenyl-5α-cholestanyl-(3β)-ester) 
• 24116-43-6 5-chloro-3β-(toluene-4-sulfonyloxy)-5α-cholestan-6β-ol 

Relevant articles and documents

Ring opening of epoxides with [18F]FeF species to produce [18F]fluorohydrin PET imaging agents

A simple technique for the preparation of [18F]HF has been developed and applied to the generation of an [18F]FeF species for opening sterically hindered epoxides. This method has been successfully employed to prepare four drug-like molecules, including 5-[18F]fluoro-6-hydroxy-cholesterol, a potential adrenal/endocrine PET imaging agent. This easily automated one-pot procedure produces sterically hindered fluorohydrin PET imaging agents in good yields and high molar activities.

Chemoselective epoxidation of cholesterol derivatives on a surface-designed molecularly imprinted Ru-porphyrin catalyst

A new molecularly imprinted Ru-porphyrin complex catalyst on a SiO2 support was designed, prepared, and characterized in a step-by-step manner for the C5C6 epoxidation of cholesterol derivatives. High chemoselectivity for the C5C6 epoxidation of cholesterol derivatives without protecting the 3-position OH group and other oxidizable functional groups was achieved on the molecularly imprinted catalyst.

Effect of Eleven Antioxidants in Inhibiting Thermal Oxidation of Cholesterol

Eleven antioxidants including nine phenolic compounds (rutin, quercetin, hesperidin, hesperetin, naringin, naringenin, chlorogenic acid, caffeic acid, ferulic acid), vitamin E (α-tocopherol), and butylated hydroxytoluene (BHT) were selected to investigate their inhibitory effects on thermal oxidation of cholesterol in air and lard. The results indicated that the unoxidized cholesterol decreased with heating time whilst cholesterol oxidation products (COPs) increased with heating time. The major COPs produced were 7α-hydroxycholesterol, 7β-hydroxycholesterol, 5,6β-epoxycholesterol, 5,6α-epoxycholesterol, and 7-ketocholesterol. When cholesterol was heated in air for an hour, rutin, quercetin, chlorogenic acid, and caffeic acid showed a strong inhibitory effect. When cholesterol was heated in lard, caffeic acid, quercetin, and chlorogenic acid demonstrated inhibitory action during the initial 0.5 h (p a high flame is recommended. If baking or deep fat frying food in oil, it is best to limit cooking time to within 0.5 h.