51529-11-4

Basic information

• Product Name: B-SITOSTERONE
• Synonyms: STIGMAST-5-EN-3-ONE;SITOSTERONE, BETA-;β-Sitosterone;SINOMENINE HYDROCHLORIDE(P);B-SITOSTERONE;BETA-SITOSTERONE
• CAS NO: 51529-11-4
• Molecular Formula: C29H48O
• Molecular Weight: 412.69
• Mol File: 51529-11-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 498.7 °C at 760 mmHg
• Flash Point: 208.1 °C
• Appearance: /
• Density: 0.97 g/cm³
• Vapor Pressure: 4.41E-10mmHg at 25°C
• Refractive Index: 1.515
• CAS DataBase Reference: B-SITOSTERONE(CAS DataBase Reference)
• NIST Chemistry Reference: B-SITOSTERONE(51529-11-4)
• EPA Substance Registry System: B-SITOSTERONE(51529-11-4)

Safety Data

• Hazardous Substances Data: 51529-11-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h10,19-21,24-27H,7-9,11-18H2,1-6H3/t20-,21-,24+,25?,26+,27+,28+,29-/m1/s1

Upstream product

• 83-46-5 β-sitosterol 

Relevant articles and documents

Phytosterols as precursors for the synthesis of aromatase inhibitors: Hemisynthesis of testololactone and testolactone

Using β-sitosterol and stigmasterol as precursor materials, a concise and efficient hemisynthesis of aromatase inhibitors: testololactone and testolactone was accomplished in a well-established reaction scheme. It involves highly effective Oppaneur oxidation of both β-sitosterol as well as stigmasterol to generate the required enone moiety in ring 'A' of the desired steroid system. The Oppaneur oxidation products of both β-sitosterol and stigmasterol were then subjected to oxidative cleavage of the side chain to produce 4-androstene-3,17-dione. Baeyer-Villiger oxidation of 4-androstene-3,17-dione using m-CPBA yielded testololactone. Dehydrogenation of 4-androstene-3,17-dione using phenylselenyl chloride in ethyl acetate followed by selenoxide elimination with H2O2 in dichloromethane furnished androstenedienone. Baeyer-Villiger oxidation of the resulting androstenedienone yielded the desired testolactone (overall yield 33%). This expeditious reaction scheme may be exploited for the bulk production of aromatase inhibitors (especially testolactone marketed under the brand name Teslac) from the most abundant and naturally occurring phytosterols like β-sitosterol.

Chromatographic separation of putative precursors of cholestanol

This paper describes convenient syntheses for labeled and unlabeled cholest-5-en-3-one, cholest-4-en-3-one, epicholesterol, cholest-4-en-3β-ol, and cholest-4-en-3α-ol. The thin-layer chromatography, high-performance liquid chromatography, and gas-liquid chromatography of these compounds and of cholestanol and epicholestanol are also described. The synthesized compounds are potential precursors in the biosynthesis of cholestanol in mammals.

A facile synthesis of [3α-3H]β-sitosterol

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