1452-34-2

Basic information

• Product Name: 2-alpha-bromo-5-alpha-cholestan-3-one
• Synonyms: (2alpha,5alpha)-2-bromocholestan-3-one
• CAS NO: 1452-34-2
• Molecular Formula: C₂₇H₄₅BrO
• Molecular Weight: 465.5496
• Mol File: 1452-34-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 499.6°C at 760 mmHg
• Density: 1.108g/cm³
• Vapor Pressure: 4.09E-10mmHg at 25°C
• Refractive Index: 1.515
• CAS DataBase Reference: 2-alpha-bromo-5-alpha-cholestan-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-alpha-bromo-5-alpha-cholestan-3-one(1452-34-2)
• EPA Substance Registry System: 2-alpha-bromo-5-alpha-cholestan-3-one(1452-34-2)

Safety Data

• Hazardous Substances Data: 1452-34-2(Hazardous Substances Data)

Usage

Properties

1. Compound type: steroid
2. Class: cholestanones
3. Functional groups: bromine atom at 2-alpha position, ketone group at 3 position
4. Derivative of: cholesterol
5. Application: research and pharmaceutical
6. Used for: studying steroid metabolism and developing drugs for hormonal disorders

Specific content

1. Name: 2-alpha-bromo-5-alpha-cholestan-3-one
2. Position of bromine atom: 2-alpha
3. Position of ketone group: 3
4. Application: research, pharmaceutical
5. Use: study steroid metabolism, develop drugs for hormonal disorders
6. Therapeutic potential: treatment of certain medical conditions

Upstream product

• 56-23-5 tetrachloromethane 
• 128-08-5 N-Bromosuccinimide 
• 566-88-1 dihydrocholesterone 
• 2439-85-2 N-bromophthalimide 
• 1255-89-6 5α-cholest-2-en-3-ol 3-acetate 
• 64-19-7 acetic acid 
• 10035-10-6 hydrogen bromide 
• 7726-95-6 bromine 
• 80-97-7 Cholestanol 
• 1255-89-6 3-Acetoxy-5α-Δ²-Cholesten 
• 57-88-5 cholesterol 
• 39416-48-3 pyridinium hydrobromide perbromide 
• 20780-35-2 5α-cholest-14-en-3β-ol 

Downstream Products

• 76302-95-9 5',6'-diphenyl-5α-cholest-2-eno<2,3-b>-(imidazo<2,1-b>thiazole) 
• 1373266-42-2 2α-[4-(4-tert-butylphenyl)-1H-1,2,3-triazol-1-yl]-5α-cholestan-3-one 
• 1373266-41-1 2α-[4-(4-propylphenyl)-1H-1,2,3-triazol-1-yl]-5α-cholestan-3-one 
• 1373266-40-0 2α-[4-(4-ethylphenyl)-1H-1,2,3-triazol-1-yl]-5α-cholestan-3-one 
• 1373266-39-7 2α-[4-(3-tolyl)-1H-1,2,3-triazol-1-yl]-5α-cholestan-3-one 
• 1373266-38-6 2α-[4-(4-tolyl)-1H-1,2,3-triazol-1-yl]-5α-cholestan-3-one 
• 1373266-37-5 2α-(4-phenyl-1H-1,2,3-triazol-1-yl)-5α-cholestan-3-one 
• 1373266-59-1 2α-(4-cyclohexyl-1H-1,2,3-triazol-1-yl)-3α-hydroxy-5α-cholestane 
• 1373266-69-3 2α-(4-cyclohexyl-1H-1,2,3-triazol-1-yl)-3β-hydroxy-5α-cholestane 
• 1373266-57-9 3α-hydroxy-2α-[4-(2-methoxyphenyl)-1H-1,2,3-triazol-1-yl]-5α-cholestane 
• 1373266-67-1 3β-hydroxy-2α-[4-(2-methoxyphenyl)-1H-1,2,3-triazol-1-yl]-5α-cholestane 
• 1373266-56-8 3α-hydroxy-2α-[4-(4-methoxyphenyl)-1H-1,2,3-triazol-1-yl]-5α-cholestane 
• 1373266-66-0 3β-hydroxy-2α-[4-(4-methoxyphenyl)-1H-1,2,3-triazol-1-yl]-5α-cholestane 
• 1373266-55-7 2α-[4-(4-tert-butylphenyl)-1H-1,2,3-triazol-1-yl]-3α-hydroxy-5α-cholestane 

Relevant articles and documents

Addressable Cholesterol Analogs for Live Imaging of Cellular Membranes

Cholesterol is an essential component of most biological membranes and serves important functions in controlling membrane integrity, organization, and signaling. However, probes to follow the dynamic distribution of cholesterol in live cells are scarce and so far show only limited applicability. Herein, we addressed this problem by synthesizing and characterizing a class of versatile and clickable cholesterol-based imidazolium salts. We show that these cholesterol analogs faithfully mimic the biophysical properties of natural cholesterol in phospholipid mono- and bilayers, and that they integrate into the plasma membrane of cultured and primary human cells. The membrane-incorporated cholesterol analogs can be specifically labeled by click chemistry and visualized in live-cell imaging experiments that show a distribution and behavior comparable with that of endogenous membrane cholesterol. These results indicate that the cholesterol analogs can be used to reveal the dynamic distribution of cholesterol in live cells. Cholesterol is an important component of biological membranes, but probes recording its dynamic intracellular distribution are scarce. Rakers et al. developed cholesterol-derived imidazolium salts mimicking properties of natural cholesterol. Following specific labeling via click chemistry, one of the cholesterol analogs was shown to incorporate into cellular membranes equivalent to endogenous cholesterol.

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Efficient synthesis of novel A-ring-substituted 1,2,3- triazolylcholestanederivatives via catalytic azide-alkyne cycloaddition

A simple and convenient synthetic route is reported for the formation of novel 2α-triazolylcholestane derivatives. The scheme involves transformation of the starting cholestanone to the corresponding azido compound and efficient conversions of 2α-azido-5α-cholestan-3-one (3) with various terminal alkynes through use of the 'click' chemistry approach. Finally, the oxo group of these heterocyclic steroidal derivatives was reduced, and the resultant mixtures of epimeric triazolyl alcohols were separated. The antiproliferative activities of the synthesized 2-triazolyl-3-ketones against three human cancer cell lines were screened. Nevertheless, only a few of the tested compounds exerted moderate cell-growth inhibition. ARKAT-USA, Inc.

STEREOCHIMIE-LVII ETUDE STEREOCHIMIQUE ET CINETIQUE DE LA BROMATION D'ESTERS ET D'ETHERS ENOLIQUES STEROIDIQUES

Absolute rates of bromination were measured for two series of derivatives of steroidal ketones 3, enol acetates 1 and enol methyl ether 2.Axial substituents exhibited a large effect on rates, which increased by 15,000 fold on going from (X=CH3; Y=CN) to (X=Y=H).From the bromide ion effect it was concluded that the first step (formation of an intermediate bromonium ion) was reversible and that the second step (formation of haloketones 4 or 5 or of haloacetals 8 or 9) was slow compared to the first step.The intermediate was concluded to be a highly unsymmetrical bromonium ion rather than a plain oxocarbenium ion.