516-92-7

Basic information

• Product Name: 5BETA-CHOLESTAN-3ALPHA-OL
• Synonyms: (3R,5R,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol;(3R,5R,8R,9S,10S,13R,14S,17R)-17-[(1R)-1,5-dimethylhexyl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol;5β-Cholestan-3α-ol,Epicoprostanol;(3R,5R,8R,9S,10S,13R,14S,17R)-10,13-diMethyl-17-((R)-6-Methylheptan-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-ol;5BETA-CHOLESTAN-3A-OL;5BETA-CHOLESTAN-3ALPHA-OL;EPICOPROSTANOL;EPICOPROSTEROL
• CAS NO: 516-92-7
• Molecular Formula: C₂₇H₄₈O
• Molecular Weight: 388.67
• EINECS: 201-315-8
• Mol File: 516-92-7.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 455.5°Cat760mmHg
• Flash Point: 190.7°C
• Appearance: /
• Density: 0.956g/cm³
• Vapor Pressure: 3.26E-10mmHg at 25°C
• Refractive Index: 1.504
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 5BETA-CHOLESTAN-3ALPHA-OL(CAS DataBase Reference)
• NIST Chemistry Reference: 5BETA-CHOLESTAN-3ALPHA-OL(516-92-7)
• EPA Substance Registry System: 5BETA-CHOLESTAN-3ALPHA-OL(516-92-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 516-92-7(Hazardous Substances Data)

Usage

Uses

5β-Cholestan-3α-ol was used as internal standard for analysis of sterols in plasma by GC and HPLC.

Biochem/physiol Actions

5β-Cholestan-3α-ol is a sterol produced endogenously from cholesterol and has been isolated from feces of human and rats. It is derived from cholesterol by the action of intestinal microorganisms.

InChI:InChI=1/C27H48O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h18-25,28H,6-17H2,1-5H3/t19?,20-,21-,22?,23-,24?,25?,26+,27-/m1/s1

Upstream product

• 64-17-5 ethanol 
• 57-88-5 cholesterol 
• 141-52-6 sodium ethanolate 
• 57-88-5 cholesterol 
• 5493-36-7 3α-Cholestanylnitrit 
• 601-57-0 Cholest-4-en-3-one 
• 1255-88-5 5α-cholestan-3β-yl acetate 
• 4947-63-1 5α-cholestan-3β-yl acetate 
• 3986-89-8 (20S)-3-oxopregn-4-ene-20-carboxaldehyde 
• 40736-33-2 (20S)-20-hydroxymethylpregn-4-en-3-one 
• 141269-56-9 3β-benzoyloxy-5α/5β-cholestane 
• 54155-77-0 5β-cholestadien-(6,8)-yl-(3β)-acetate 
• 137637-33-3 5β-cholestadien-(6,8)-ol-(3β) 
• 137637-33-3 5α-cholesta-6,8-dien-3β-ol 

Downstream Products

• 56784-81-7 3α-(2-carboxy-benzoyloxy)-5β-cholestane 
• 56784-81-7 phthalic acid mono-(5β-cholestan-3β-yl ester) 
• 80-97-7 Coprostanol 
• 96788-94-2 3α-(toluene-4-sulfonyloxy)-5β-cholestane 
• 601-53-6 coprostanone 
• 1177-97-5 3.4-seco-5β-cholestanedioic acid-(3.4) 
• 62008-67-7 O-Cholestanylselenobenzoat 
• 909272-81-7 epi-cholestanol benzoate 
• 51646-11-8 3β-benzoyloxy-5β-cholestane 
• 117775-75-4 3α-cholestanyl m-chlorobenzoate 
• 70849-14-8 3-β-cholestanyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 70849-14-8 3-β-cholestanyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 

Relevant articles and documents

Method for synthesizing cholesterol by taking BA as raw material

The invention discloses a method for synthesizing cholesterol by taking BA as a raw material. A plant source raw material 21-hydroxy-20-methylpregna-4-en-3-one, also known as Shuangjiangchun or BA is taken as a raw material, and the cholesterol is synthesized by the steps of oxidation, Wittig reaction, acetylation, reduction, selective hydrogenation reduction and the like. The raw materials for synthesizing cholesterol are plant sources, the price is low, the safety is high, the risk of pathogenic bacteria and virus infection is avoided, and the synthesis method is easy to operate, high in yield, few in side reaction, environmentally friendly, good in economical efficiency and convenient for industrial production; and the invention solves the safety problem of the existing cholesterol product and the problems of high cost, environmental unfriendliness and unsuitability for large-scale industrial production in the synthesis technology.

Cleavage of a p-cyanobenzyl group from protected alcohols, amines, and thiols using triethylgermyl sodium

Alcohols, amines, and thiols protected with a p-cyanobenzyl group can be easily and quantitatively deprotected using triethylgermyl sodium under mild conditions.

The reaction of alkyl peroxy radicals

Secondary alkyl peroxy radicals generated from 4-phenyl-2-butyl-, 2-nonyl- and 3α-cholestanyl hydroperoxides at 45°C undergo Russell termination reactions in preference to non-terminating decomposition reactions. Non-terminating decomposition of 2-nonyl peroxy radicals afforded 2,5-nonanedione and 2,5-nonanediol due to intramolecular hydrogen abstraction reactions of alkoxy radicals. The radicals derived from 2-methyl-4-phenyl-2-butyl-, 2-methyl-5-phenyl-2-pentyl- and 2-methyl-6-phenyl-2-hexyl hydroperoxides afforded benzylic functionalized products due to intermolecular reactions. 2-Hexylperoxy radicals generated in excess alcohols ineffectively abstracted the α-hydrogens of alcohols. These results demonstrate the low reactivity of alkyl peroxy radicals.