17137-70-1

Basic information

• Product Name: Cholest-7-en-3β-ol acetate
• Synonyms: Cholest-7-en-3β-ol acetate
• CAS NO: 17137-70-1
• Molecular Formula: C₂₉H₄₈O₂
• Molecular Weight: 428.6902
• Mol File: 17137-70-1.mol

Chemical Properties

• Boiling Point: 493.3°Cat760mmHg
• Flash Point: 248.8°C
• Appearance: /
• Density: 0.99g/cm³
• Vapor Pressure: 7.13E-10mmHg at 25°C
• Refractive Index: 1.515
• CAS DataBase Reference: Cholest-7-en-3β-ol acetate(CAS DataBase Reference)
• NIST Chemistry Reference: Cholest-7-en-3β-ol acetate(17137-70-1)
• EPA Substance Registry System: Cholest-7-en-3β-ol acetate(17137-70-1)

Safety Data

• Hazardous Substances Data: 17137-70-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C29H48O2/c1-19(2)8-7-9-20(3)25-12-13-26-24-11-10-22-18-23(31-21(4)30)14-16-28(22,5)27(24)15-17-29(25,26)6/h11,19-20,22-23,25-27H,7-10,12-18H2,1-6H3

Upstream product

• 110-86-1 pyridine 
• 40823-41-4 acetic acid-(7α-hydroxy-5α-cholestanyl-(3β)-ester) 
• 98-59-9 p-toluenesulfonyl chloride 
• 80-99-9 lathosterol 
• 108-24-7 acetic anhydride 
• 127-08-2 potassium acetate 
• 64-19-7 acetic acid 
• 434-16-2 7-dehydrocholesterol 
• 1059-86-5 7-Dehydrocholesteryl acetate 
• 56-23-5 tetrachloromethane 
• 7758-99-8 copper(II) sulfate 
• 802294-64-0 propionic acid 
• 40823-16-3 acetic acid-(7β-hydroxy-5α-cholestanyl-(3β)-ester) 
• 57-88-5 cholesterol 

Downstream Products

• 80-99-9 lathosterol 
• 6562-21-6 3β-(Acetyloxy)-5α-cholest-8(14)-ene 
• 2665-03-4 [choleste-7-ene-3-oxy]trimethylsilane 
• 69140-15-4 3β-hydroxy-5α-cholest-8-en-7-one 
• 566-29-0 3β-hydroxy-5α-cholest-8(14)-en-7-one 
• 50673-97-7 15-Ketocholestene 
• 34227-11-7 3β-hydroxy-5α-cholesta-7,14-diene 
• 69140-06-3 5α-cholest-8(14)-ene-3β,7α-diol 
• 566-99-4 5α-cholest-8(14)-en-3β-ol 
• 34495-42-6 3β-acetoxy-5α-cholest-8(14)-en-15-one 
• 116561-41-2 3β-acetoxy-5α-cholest-8(14)-en-7-one-(p-toluene-sulfonylhydrazone) 
• 15459-85-5 5α-cholest-7-en-3-one 
• 16780-48-6 3β-acetoxy-8α,14α-epoxy-5α-cholestan-7-one 
• 53755-39-8 (3S,5S,7S,8S,9R,10S,13R,14R,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopropa[7,8]cyclopenta[a]phenanthren-3-ol 

Relevant articles and documents

Synthesis of fluorinated steroids using a novel fluorinating reagent tetrabutylammonium difluorodimethylphenylsilicate (TAMPS)

Steroidal 3-fluoroderivatives were prepared from corresponding tosylates using tetrabutyl-ammonium difluorodimethylphenylsilicate as fluorinating agent. The reaction was tested on all four possible C-3 and C-5 stereoisomers of cholestane and 17-oxoandrostane skeletons. In this reaction only one isomer was always formed with opposite configuration at C-3 to starting tosylate. The reaction is accompanied by elimination which affords a mixture of corresponding olefines.

Preparation of steroid olefins from heptafluorobutyrates

Steroids with hydroxyl group in positions 2, 3, 6, 7, 17 and 20 were esterified with heptafluorobutyric anhydride. The obtained esters on treatment with lithium bromide in N,N-dimethylacetamide in the presence of pyridinium tosylate afforded the corresponding olefins in high yields.

Epoxide Cleavage Reactions of 7α,8α- and 7β,8β-Epoxycholestanol Acetates

In a search for an alternative synthetic route to 32-oxygenated sterol derivatives such as 5, 7α,8α- and 7β,8β-epoxycholestanol acetate (9 and 10) were subjected to various conditions of epoxide cleavage.The trans-diaxial opening of the α-epoxide 9 with lithium/ethylamine gave the 7α-ol 11, whereas the 8β-ol 12 was produced from the β-epoxide 10 on reduction with lithium aluminum hydride.However, the trans-diaxal 8β-halo(or hydroxy)-7α-ols were not obtained at all on treatment of the α-epoxide 9 with various mineral acids or BF3-etherate in benzene.Under these conditions, the C-8 carbenium ion would be the intermediate, from which the 7-ketone 13 and a mixture of Δ6,8-, Δ7,14- and/or Δ8,14-diene compounds 16, as well as Δ8(9)- and Δ8(14)-7α-ol 14 and 4a, were produced.The latter allylic alcohol 4a, a possible synthetic precursor of 32-oxygenated sterol was prepared in 63percent yield when benzene was replaced with tetrahydrofuran in the BF3-etherate-catalyzed reaction of the α-epoxide 9.Keywords-epoxide cleavage; 32-oxygenated sterol; 7α,8α-epoxycholestanol acetate; 7β,8β-epoxycholestanol acetate; 3β-acetoxycholest-8(14)-en-7α-ol; reduction; acid treatment; boron trifluoride-etherate; long-range 13C-1H COSY

A Simple Method for the Reduction of the 7,8-Double Bond of Steroidal 5,7-Dienes

1,4-Cycloadducts of various steroidal 5,7-dienes and 4-phenyl-1,2,4-triazoline-3,5-dione gave a separable mixture (3 : 2) of the corresponding Δ5- and Δ7-sterols in good yield when treated with lithium dissolved in refluxing ethylamine.

Studies on the Constituents of Pollen. X. On the Constituents of Pollen Grains of Ambrosia elatior LINNE

The new sterols 4α,14-dimethyl-9,19-cyclocholestan-3β,24ξ-diol (IIIa) and 4α,14-dimethyl-9,19-cyclocholestan-3β,24ξ,25-triol (IVa) were isolated, together with lophenone, lophenol, and cholest-7-en-3β-ol, from the pollen grains of Ambrosia elatior LINNE.The structures were elucidated on the basis of spectroscopic studies and chemical evidence.Keywords-Ambrosia elatior LINNE; Compositae; pollen grains; lophenone; lophenol; cholest-7-en-3β-ol; 4α,14-dimethyl-9,19-cyclocholestan-3β,24ξ-diol; 4α,14-dimethyl-9,19-cyclocholestan-3β,24ξ,25-triol