3381-54-2

Basic information

• Product Name: Methanesulfonic acid 3β-cholesteryl ester
• Synonyms: Cholest-5-en-3β-ol methanesulfonate;Cholesterol methanesulfonate;Methanesulfonic acid 3β-cholesteryl ester;Methanesulfonic acid cholest-5-en-3β-yl ester
• CAS NO: 3381-54-2
• Molecular Formula: C₂₈H₄₈O₃S
• Molecular Weight: 464.74392
• Mol File: 3381-54-2.mol
• Article Data: 24

Chemical Properties

• Boiling Point: 560°Cat760mmHg
• Flash Point: 292.5°C
• Appearance: /
• Density: 1.06g/cm³
• Vapor Pressure: 5.36E-12mmHg at 25°C
• Refractive Index: 1.526
• CAS DataBase Reference: Methanesulfonic acid 3β-cholesteryl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Methanesulfonic acid 3β-cholesteryl ester(3381-54-2)
• EPA Substance Registry System: Methanesulfonic acid 3β-cholesteryl ester(3381-54-2)

Safety Data

• Hazardous Substances Data: 3381-54-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C28H48O3S/c1-19(2)8-7-9-20(3)24-12-13-25-23-11-10-21-18-22(31-32(6,29)30)14-16-27(21,4)26(23)15-17-28(24,25)5/h10,19-20,22-26H,7-9,11-18H2,1-6H3/t20-,22+,23+,24-,25+,26+,27+,28-/m1/s1

Upstream product

• 57-88-5 cholesterol 
• 124-63-0 methanesulfonyl chloride 
• 80-97-7 Cholestanol 
• 31138-45-1 9-cholesteroxy-9-phenylanthrone 
• 77588-15-9 Cholesteryl-4-methoxybenzolsulfonat 
• 1182-65-6 cholesteryl p-toluenesulfonate 
• 57-88-5 cholesterol 
• 57-88-5 cholesterol 

Downstream Products

• 2930-80-5 cholesteryl iodide 
• 516-91-6 (3S,8S,9S,10R,13R,14S,17R)-3-Bromo-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 
• 910-31-6 cholesteryl chloride 
• 1433-82-5 3-β-azido-5-cholestene 
• 30788-35-3 2-(((3S,8S,9S,10R,13R,14S)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)ethan-1-ol 
• 75014-44-7 8-(cholest-5-en-3β-yloxy)-3,6-dioxaoctane-1-ol 
• 1357271-66-9 C₃₅H₅₁N₃ 
• 42921-42-6 cholest-5-en-3α-ol benzoate 
• 38759-52-3 3β-Acrylamido-5-cholesten 
• 38759-53-4 3β-Isobutyramido-5-cholesten 
• 57-88-5 cholesterol 
• 570-74-1 cholest-5-ene 
• 2864-50-8 sodium (20R)-5-cholesten-3β-yl sulfate 

Relevant articles and documents

Effective gene-silencing of siRNAs that contain functionalized spacer linkages within the central region

Short-interfering RNAs containing a variety of functional groups at the central region of the sense strand were synthesized and evaluated. The gene-silencing data suggest that these siRNAs are biocompatible and are very effective in cell-based assays.

A Simple Synthesis of Steroidal 3α,5-Cyclo-6-ones and their Efficient Transformation to Steroidal 2-En-6-ones

Sterols 1 were converted to 3α-5-cyclo-6-ones 4 via their mesylates and subsequent oxidation.Refluxing 4 with sodium bromide/p-toluene sulfonic acid in dimethylformamide gave steroidal 2-en-6-ones 5, among which 5 is an important brassinolide intermediate.

Synthesis and antitumor activity of novel steroidal imidazolium salt derivatives

Sixty-one novel steroidal imidazolium salt derivatives were synthesized and evaluated in vitro against a panel of human tumor cell lines. The results showed that diosgenin?imidazolium salt derivatives displayed much higher cytotoxic activities than choles

Apoptosis inducing properties of 3-biotinylate-6-benzimidazole B-nor-cholesterol analogues

In this work, a series of Biotin-substituted B-nor-cholesteryl benzimidazole compounds were synthesized. The antiproliferative activities of these compounds were evaluated in vitro using a series of human cancer cell lines, including HeLa (cervical cancer), SKOV3 (ovarian cancer), T-47D (thymus gland cancer), MCF-7 (human breast cancer) and HEK293T (normal renal epithelial) cells. These compounds displayed distinct antiproliferative activities against the currently tested cancer cells. The apoptotic properties induced by compound 6d were further investigated. Our results showed that compound 6d could induce the apoptosis of SKOV3 cells, blocking the cell growth in S-phase. Western blotting analyses revealed that compound 6d can induce cell apoptosis via the mitochondria-dependent pathway.

Steroid compound 3-site hydroxyl configuration inversion method

The invention discloses a steroid compound 3-site hydroxyl configuration inversion method. The method specifically comprises the following steps that (1) a steroid compound containing a 3-site hydroxyl reacts with an acyl chloride compound; (2) the product obtained in the step (1) and a substituting agent are subjected to SN2 nucleophilic substitution reaction under existing of a phase transfer catalyst; and (3) the product obtained in the step (2) is subjected to a hydrolysis reaction. Compared with a Mitsunobu method, the method does not need to use triphenylphosphine and azodiformate pricedhigher, and accordingly the production cost is greatly lowered; meanwhile, a p-nitrobenzoic acid derivative which seriously affects the water environment does not need to be used, and therefore the method is more environmentally friendly. The method adopts cesium acetate/18-crown ether-6 system to conduct 3-site hydroxyl configuration inversion, can remarkably reduce occurrence of side reactions,accordingly a higher reaction yield is obtained, and the method is finally applicable to industrialized production.