120152-00-3

Basic information

• Product Name: 9,11-epoxycholest-7-ene-3,5,6-triol
• Synonyms: 9,11-epoxycholest-7-ene-3,5,6-triol
• CAS NO: 120152-00-3
• Molecular Formula: C27H44 O4
• Molecular Weight: 432.64
• Mol File: 120152-00-3.mol

Chemical Properties

• Boiling Point: 556.1°Cat760mmHg
• Flash Point: 290.1°C
• Appearance: /
• Density: 1.15g/cm³
• Vapor Pressure: 1.1E-14mmHg at 25°C
• Refractive Index: 1.57
• CAS DataBase Reference: 9,11-epoxycholest-7-ene-3,5,6-triol(CAS DataBase Reference)
• NIST Chemistry Reference: 9,11-epoxycholest-7-ene-3,5,6-triol(120152-00-3)
• EPA Substance Registry System: 9,11-epoxycholest-7-ene-3,5,6-triol(120152-00-3)

Safety Data

• Hazardous Substances Data: 120152-00-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C27H44O4/c1-16(2)7-6-8-17(3)19-9-10-20-21-13-22(29)26(30)14-18(28)11-12-25(26,5)27(21)23(31-27)15-24(19,20)4/h13,16-20,22-23,28-30H,6-12,14-15H2,1-5H3/t17-,18+,19?,20+,22-,23-,24-,25+,26+,27?/m1/s1

Upstream product

• 133565-77-2 9α,11α-epoxy-3β,5-dihydroxy-5α-cholest-7-en-6-one 
• 463932-03-8 9α,11α-epoxy-5-hydroxy-5α-cholest-7-en-3β,6β-diol 3,6-diacetate 
• 2551-04-4 5α,6β-dihydroxy-5α-cholest-7-en-3β-yl acetate 
• 2551-05-5 5-hydroxy-5α-cholest-7-en-3β,6β-diol 3,6-diacetate 
• 157396-30-0 5-hydroxy-5α-cholesta-7,9(11)-dien-3β,6β-diol 3,6-diacetate 
• 133565-76-1 3β,5-dihydroxy-5α-cholesta-7,9(11)-diene-6-one 

Relevant articles and documents

CH3ReO3-catalyzed oxidation of cholesta-5,7-dien-3β-yl acetate with the urea-hydrogen peroxide adduct under various conditions. Synthesis of the natural epoxy sterol 9α,11α-epoxy-5α-cholest-7-en-3β,5,6β-triol

This article describes the oxidation of cholesta-5,7-dien-3β-yl acetate (4) with the urea-hydrogen peroxide adduct (UHP) using methyltrioxorhenium (MTO) as catalyst, under various conditions. Specifically, the effects of using different solvents (CHCl3 and ethers) and additives (EtOH and pyridine) on the course of the MTO-catalyzed oxidation of 4 were investigated. Some new steroids (6, 9, 10 and 11), obtained from this oxidation, were isolated and characterized on the basis of chemical evidence and interpretation of spectroscopic data including H-H COSY and HMBC experiments. The optimal solvent for the oxidation of 4 with MTO/UHP oxidizing system was diethyl ether. In this solvent the reaction is clean and gave as the main product 5,6β-dihydroxy-5α-cholest-7-en-3β-yl acetate (8, 65% yield), obtained with a more simple procedure and with a higher yield than that reported in literature. Sterol 8 is a key intermediate compound in the synthesis of many steroids of marine origin, biologically active, oxygenated at the B/C rings. In fact, starting from diol 8, we performed the synthesis of the natural cytotoxic epoxy sterol 9α,11α-epoxy-5α-cholest-7-en-3β,5,6β-triol (15, 21% yield) with an improvement in yield and number of steps over a synthesis of the same natural product previously reported. When the oxidation of 4 with the MTO/UHP system in diethyl ether was performed in the presence of pyridine as ligand, the unsaturated epoxide 5,6α-epoxy-5α-cholest-7-en-3β-yl acetate (10, 90% yield) was obtained after only 5 min in good yield. In fact, pyridine, besides having beneficial effect on the reaction rate, shuts down the ring opening reactions, as reported in literature.

Synthesis of the marine epoxy sterol 9α,11α-epoxy-5α-cholest-7-ene-3β,5,6β-triol

The synthesis of 9α,11α-epoxy-5α-cholt'st-7-ene-3β,5,6β-triol (1), a highly oxygenated marine sterol containing a 9,11-epoxide moiety in the nucleus, is described. Epoxy sterol 1 was synthesized from cholesta-5,7-dien-3β-ol. Oxidation of this sterol with m-chloroperbenzoic acid followed by hydrolysis and acetylotion furnished 5α-cholest-7-ene-3β,5,6α-triol 3,6-diacetate (2). Mercuric acetate dehydrogenation of diacetate 2, followed by oxidation with manganese dioxide and epoxidation with m-chloroperbenzoic acid, afforded 9α,11α-epoxy-3β,5-dihydroxy-5α-cholest-7-en-6-one (5). Reduction of 5 with lithium aluminum hydride gave the desired compound 1. The structures of all synthetic intermediates were confirmed by 1H and 13C nuclear magnetic resonance (NMR) spectroscopy. A reassignment of resonances for carbons 1, 8, and 15 in the 13C NMR spectrum of 1, based on 2D-NMR correlation spectroscopy, has been accomplished.