40824-59-7

Basic information

• Product Name: 7a-Hydroxycholesterol3-Benzoate
• Synonyms: (3,7a)-Cholest-5-ene-3,7-diol 3-Benzoate;7a-Hydroxycholesterol3-Benzoate;Cholest-5-ene-3,7a-diol 3-Benzoate;(3β,7α)-Cholest-5-ene-3,7-diol 3-Benzoate;Cholest-5-ene-3β,7α-diol 3-Benzoate
• CAS NO: 40824-59-7
• Molecular Formula: C₃₄H₅₀O₃
• Molecular Weight: 506.77
• Product Categories: Steroids
• Mol File: 40824-59-7.mol
• Article Data: 1

Chemical Properties

• Melting Point: 160.5-161.5°C
• Boiling Point: 595.042°C at 760 mmHg
• Flash Point: 218.194°C
• Appearance: /
• Density: 1.08g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.557
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate
• PKA: 14.02±0.70(Predicted)
• CAS DataBase Reference: 7a-Hydroxycholesterol3-Benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: 7a-Hydroxycholesterol3-Benzoate(40824-59-7)
• EPA Substance Registry System: 7a-Hydroxycholesterol3-Benzoate(40824-59-7)

Safety Data

• Hazardous Substances Data: 40824-59-7(Hazardous Substances Data)

Usage

Description

7a-Hydroxycholesterol3-Benzoate, also known as (3β,7α)-Cholest-5-ene-3,7-diol 3-Benzoate, is a chemical compound with the CAS number 40824-59-7. It is derived from cholesterol and features a benzoate group attached to the 3-hydroxyl position. This modification endows it with unique chemical properties and potential applications in various fields.

Uses

Used in Organic Synthesis:
7a-Hydroxycholesterol3-Benzoate is used as an intermediate in organic synthesis for the preparation of various complex organic molecules and pharmaceutical compounds. Its unique structure allows for selective functionalization and modification, making it a valuable building block in the synthesis of biologically active molecules and specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 7a-Hydroxycholesterol3-Benzoate is used as a precursor for the synthesis of cholesterol-derived drugs. Its specific functional groups enable the development of novel therapeutic agents with potential applications in treating various diseases and medical conditions.
Used in Chemical Research:
7a-Hydroxycholesterol3-Benzoate is also utilized in chemical research as a model compound for studying the reactivity and properties of cholesterol and its derivatives. This helps researchers gain insights into the structure-activity relationships and design new molecules with improved properties and applications.

InChI:InChI=1/C34H50O3/c1-22(2)10-9-11-23(3)27-14-15-28-31-29(17-19-34(27,28)5)33(4)18-16-26(20-25(33)21-30(31)35)37-32(36)24-12-7-6-8-13-24/h6-8,12-13,21-23,26-31,35H,9-11,14-20H2,1-5H3/t23-,26+,27?,28+,29+,30-,31?,33+,34-/m1/s1

Upstream product

• 6997-41-7 3β-benzoyloxy-cholest-5-en-7-one 
• 65942-28-1 7β-bromocholest-5-en-3β-ol benzoate 
• 604-32-0 cholesteryl benzoate 
• 566-26-7 (3S,7S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol 
• 98-88-4 benzoyl chloride 
• 26048-46-4 7α-bromocholest-5-en-3β-ol benzoate 
• 566-28-9 7-Oxocholesterol 
• 17974-80-0 3β,7β-cholest-5-ene-3,7-diol-3-benzoate 
• 809-51-8 7-ketocholesteryl acetate 

Downstream Products

• 566-26-7 (3S,7S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol 

Relevant articles and documents

A convenient synthesis of 7α-hydroxycholest-4-en-3-one by the hydroxypropyl-β-cyclodextrin-facilitated cholesterol oxidase oxidation of 3β,7α-cholest-5-ene-3,7-diol

The initial biosynthetic conversions of cholesterol to the bile acids involve sequential 7α-hydroxylation (catalyzed by cholesterol 7α-hydroxylase) followed by C-3 oxidation and concomittant double bond migration (to a Δ4-configuration, catalyzed by 3β-Δ5-C27-steroid oxidoreductase) to provide 7α-hydroxycholest-4-en-3-one.A straightforward, and economical, preparation (on a 0.1 g scale) of this pivotal biosynthetic intermediate has been devised.Reduction of 3β-(benzoyloxy)-cholest-5-en-7-one with LiB(sec-butyl)3H provided a 4:1 mixture, respectively, of the 7α- and 7β-hydroxy diastereomers, which were separated chromatographically.Solvolytic removal of the C-3 benzoyl group gave 3β,7α-cholest-5-ene-3,7-diol.A suspension of the 1:1 (v/v) complex (formed by mutual dissolution in MeOH, followed by evaporation of the solvent) of this diol with hydroxypropyl-β-cyclodextrin, at a concentration of 1 mg mL-1 (in neutral phosphate buffer), was converted by Brevibacterium sp cholesterol oxidase (0.25 U mg-1 of substrate) and catalase (70 U mg-1 of substrate, to recover O2 from the H2O2 produced by the enzymatic oxidation) to a suspension of 7α-hydroxycholest-4-en-3-one and the hydroxypropyl-β-cyclodextrin.The yield for the enzymatic conversion was in excess of 90percent.A much poorer and less reproducible yield ( 20percent) was seen in the absence of the hydroxypropyl-β-cyclodextrin.Routine extraction of this aqueous suspension, and chromatographic purification (85:15 CHCl3/acetone v/v on silica) of the residue, gave pure 7α-hydroxycholest-4-en-3-one in 68percent isolated yield.This route is a significant improvement, in terms of reaction scale and convenience, over the previous procedures for the preparation of this steroid. - Keywords: (7α)-hydroxycholesterol; hydroxypropyl-β-cyclodextrin; cholesterol oxidase; (7α)-hydroxycholest-4-en-3-one; bile acid biosynthesis; cholesterol 7α-hydroxylase