14982-53-7

Basic information

• Product Name: cholestane
• Synonyms: Cholestane; NSC 140722; Cholestane (VAN) (8CI)(9CI); (5alpha,17alpha,20S)-cholestane
• CAS NO: 14982-53-7
• Molecular Formula: C₂₇H₄₈
• Molecular Weight: 372.67
• EINECS: 239-062-0
• Mol File: 14982-53-7.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 440.9°C at 760 mmHg
• Flash Point: 210.3°C
• Density: 0.91g/cm³
• Vapor Pressure: 1.47E-07mmHg at 25°C
• Refractive Index: 1.492
• CAS DataBase Reference: cholestane(CAS DataBase Reference)
• NIST Chemistry Reference: cholestane(14982-53-7)
• EPA Substance Registry System: cholestane(14982-53-7)

Safety Data

• Hazardous Substances Data: 14982-53-7(Hazardous Substances Data)

Usage

Description

Cholestane is a naturally occurring saturated hydrocarbon and a steroid compound with the molecular formula C27H48. It is found in plants and animals and serves as a key precursor in the biosynthesis of cholesterol and other important steroid hormones in the body. Cholestane's stable and non-reactive nature makes it a valuable compound for a wide range of scientific and industrial applications.

Uses

Used in Pharmaceutical Development:
Cholestane is used as a key precursor in the development of pharmaceuticals targeting cholesterol and steroid hormone regulation. Its role in the biosynthesis of cholesterol and other important steroid hormones makes it a crucial component in the creation of medications that address various health conditions related to hormonal balance and cholesterol levels.
Used in Research and Analytical Chemistry:
Cholestane is used as a standard reference material for mass spectrometry and other analytical techniques in the study of steroid metabolism and endocrine function. Its stable and non-reactive nature allows for accurate and reliable measurements in these scientific fields, contributing to a better understanding of the complex processes involved in hormone regulation and metabolism.
Used in Industrial Applications:
Cholestane's stable and non-reactive nature also makes it a valuable compound for various industrial applications. Its use in the development of pharmaceuticals and as a standard reference material for analytical techniques highlights its versatility and importance in both scientific research and commercial industries.

Upstream product

• 54339-68-3 4-cholestene-3,6-dione 
• 57-88-5 cholesterol 
• 27409-41-2 3-hydroxy-cholestane 
• 141269-57-0 cholestan-3-yl 4-methylbenzoate 
• 543-27-1 isobutyl chloroformate 
• 17608-41-2 cholestanol 
• 3464-60-6 cholesta-1,4,6-trien-3-one 
• 16734-07-9 O-3β-cholestanyl S-methyl dithiocarbonate 
• 139342-50-0 Thiocarbonic acid O-[(3S,8R,9S,10S,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl] ester O-(4-fluoro-phenyl) ester 
• 26430-35-3 p-toluene-sulphonyl-hydrazone of cholestanone 
• 130534-82-6 Thiocarbonic acid O-[(3S,5S,10S,13R,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl] ester O-(4-fluoro-phenyl) ester 
• 5211-17-6 β-Cholestanyl-S-methyl-xanthat 

Relevant articles and documents

Novel electrochemical deoxygenation reaction using diphenylphosphinates

The electrochemical reduction of diphenylphosphinate esters leads smoothly and in high yields to the corresponding deoxygenated products. In comparison with the previously developed methodologies, the electrolysis could be performed at lower temperature and with a higher current density, resulting in a shorter reaction time.

Using toluates as simple and versatile radical precursors

(Chemical Equation Presented) The viability of the toluate moiety as a radical precursor has been examined by studying deoxygenation and cyclization reactions.

Chemoselective reduction of 1,4,6-cholestatrien-3-one and 1,4,6-androstatriene-3,17-dione by various hydride reagents

The chemoselectivity of rigid cyclic α,β-unsaturated carbonyl group on the reducing agents was influenced by the ring size and steric factor. Cholesterol (cholest-5-en-3β-ol) and dehydroepiandrosterone (DHEA) were oxidized with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone to form 1,4,6-cholestatrien-3-one and 1,4,6-androstatriene-3,17-dione. They were reduced with NaBH4, lithium tri-sec-butylborohydride (l-Selectride), LiAlH4, 9-borabicyclo[3.3.1]nonane (9-BBN), lithium triethylborohydride (Super-hydride), and BH3·(CH3)2S in various conditions, respectively. Reduction of 1,4,6-cholestatrien-3-one and 1,4,6-androstatriene-3,17-dione by NaBH4 (4 equiv.) produced 4,6-cholestadien-3β-ol and 4,6-androstadiene-3β,17β-diol, respectively. Reduction by l-Selectride (12 equiv.) afforded 4,6-cholestadien-3α-ol and 4,6-androstadiene-3α,17β-diol, chemoselectively. Reaction with Super-hydride (12 equiv.) produced 4,6-cholestadien-3-one and 3-oxo-4,6-androstadien-17β-ol. Reduction of 1,4,6-cholestatrien-3-one by 9-BBN (14 equiv.) produced 1,4,6-cholestatrien-3α-ol, but 1,4,6-androstatriene-3,17-dione was not reacted with 9-BBN in the reaction conditions. Reaction of LiAlH4 (6 equiv.) formed 4,6-cholestadien-3β-ol and 3-oxo-1,4,6-androstatrien-17β-ol. Reduction of 1,4,6-cholestatrien-3-one by BH3·(CH3)2S (11 equiv.) gave cholestane as major compound and unlike reactivity of cholesterol, 1,4,6-androstatriene-3,17-dione by 8 equiv. of BH3·(CH3)2S formed 3-oxo-1,4,6-androstatrien-17β-ol. LiAlH4 and BH3·(CH3)2S showed relatively low chemoselectivity.