20835-91-0

Basic information

• Product Name: 5 alpha-stigmastane-3 beta,5,6 beta-triol 3-monobenzoate
• Synonyms: 5 alpha-stigmastane-3 beta,5,6 beta-triol 3-monobenzoate;Stigmastane-3,5,6-triol;Stigmastane-3beta,5alpha,6beta-triol
• CAS NO: 20835-91-0
• Molecular Formula: C29H52O3
• Molecular Weight: 448.7214
• Mol File: 20835-91-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 535.6°Cat760mmHg
• Flash Point: 216.1°C
• Appearance: /
• Density: 1.047g/cm³
• Vapor Pressure: 1.05E-13mmHg at 25°C
• Refractive Index: 1.531
• CAS DataBase Reference: 5 alpha-stigmastane-3 beta,5,6 beta-triol 3-monobenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: 5 alpha-stigmastane-3 beta,5,6 beta-triol 3-monobenzoate(20835-91-0)
• EPA Substance Registry System: 5 alpha-stigmastane-3 beta,5,6 beta-triol 3-monobenzoate(20835-91-0)

Safety Data

• Hazardous Substances Data: 20835-91-0(Hazardous Substances Data)

Usage

Definition

ChEBI: A 3beta-hydroxy steroid that is stigmastane substituted by hydroxy groups at positions 3, 5 and 6 (the 3beta,5alpha,6beta stereoisomer). It has been isolated from the roots of Brey ia fruticosa.

InChI:InChI=1/C29H52O3/c1-7-20(18(2)3)9-8-19(4)23-10-11-24-22-16-26(31)29(32)17-21(30)12-15-28(29,6)25(22)13-14-27(23,24)5/h18-26,30-32H,7-17H2,1-6H3/t19-,20-,21+,22+,23-,24+,25+,26-,27-,28-,29+/m1/s1

Upstream product

• 83-46-5 β-sitosterol 
• 87303-93-3 5α,6α- and 5β,6β-Epoxystigmastan-3β-ol 
• 32345-19-0 24-ethylcholesta-5,22-dien-3β-ol 
• 53139-42-7 stigmasteryl tosylate 
• 108646-29-3 22,23-dihydro-i-stigmasterol methyl ether 
• 915-05-9 stigmast-5-en-3-yl acetate 
• 7722-84-1 dihydrogen peroxide 
• 64-19-7 acetic acid 

Downstream Products

• 23670-94-2 stigmast-4-ene-3,6-dione 
• 55051-78-0 (24R)-3β,5α-dihydroxy-24-ethyl-5α-cholestan-6-one 
• 77551-74-7 stigmastan-3,6-dione 

Relevant articles and documents

Efficient trans-diaxial hydroxylation of Δ5-steroids

A convenient, fast, and high-yielding process to synthesize 5α,6β-dihydroxysteroids directly from the correspondent Δ5-steroids is reported. The reaction protocol consists in the conjugation of a readily available and stable oxidant, magnesium bis(monoperoxyphthalate) hexahydrate, with the non-toxic bismuth(III) triflate in acetone to afford the trans-diaxial hydroxylation product in a stepwise manner and in excellent yields.

Gram-scale chromatographic purification of β-sitosterol: Synthesis and characterization of β-sitosterol oxides

An effective purification method for β-sitosterol was developed starting from a commercial source of a phytosterol mixture using preparative adsorption column chromatography. β-Sitosterol (≥95% purity) was obtained on a gram-scale. Thus, the synthesis of six β-sitosterol oxides, including 7α-hydroxy, 7β-hydroxy, 5,6α-epoxy, 5,6β-epoxy, 7-keto, and 5α,6β-dihydroxysitosterol, were successfully carried out. The spectral characteristics of all the synthetic intermediates and target compounds (～95% purity) were well-documented.

Biological evaluation in vivo and in vitro of selected 5-alpha-cholestane-3-beta, 5-alpha, 6-beta-triol analogs as hypocholesterolemic agents.

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