26649-05-8

Basic information

• Product Name: (3β,22S)-Dihydroxy Cholesterol
• Synonyms: (3β,22S)-Dihydroxy Cholesterol;(20R,22S)-20,22-Dihydroxycholesterol;(22S)-Cholest-5-ene-3β,20,22-triol;(3β,22S)-Cholest-5-ene-3,20,22-triol;20α,22S-Dihydroxycholesterol;(32,22S)-Dihydroxy Cholesterol
• CAS NO: 26649-05-8
• Molecular Formula: C₂₇H₄₆O₃
• Molecular Weight: 418.65234
• Product Categories: Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Steroids
• Mol File: 26649-05-8.mol
• Article Data: 4

Chemical Properties

• Melting Point: 181-190 °C(Solv: acetone (67-64-1); chloroform (67-66-3))
• Boiling Point: 553.5±25.0 °C(Predicted)
• Appearance: /
• Density: 1.08±0.1 g/cm3(Predicted)
• PKA: 14.42±0.29(Predicted)
• CAS DataBase Reference: (3β,22S)-Dihydroxy Cholesterol(CAS DataBase Reference)
• NIST Chemistry Reference: (3β,22S)-Dihydroxy Cholesterol(26649-05-8)
• EPA Substance Registry System: (3β,22S)-Dihydroxy Cholesterol(26649-05-8)

Safety Data

• Hazardous Substances Data: 26649-05-8(Hazardous Substances Data)

Usage

Description

(3β,22S)-Dihydroxy Cholesterol, also known as 22S-hydroxycholesterol, is a metabolite of cholesterol that plays a crucial role in the synthesis of pregnenolone. It is formed through the metabolism of cholesterol by the enzyme P450scc, which converts cholesterol to pregnenolone. This metabolite is essential for the production of various steroid hormones, including cortisol, aldosterone, and testosterone.

Uses

Used in Steroid Hormone Production:
(3β,22S)-Dihydroxy Cholesterol is used as a precursor in the biosynthesis of steroid hormones for maintaining various physiological functions in the body. It is involved in the production of hormones such as cortisol, which helps regulate metabolism and the immune system; aldosterone, which plays a role in maintaining electrolyte balance and blood pressure; and testosterone, which is essential for the development of male reproductive tissues and secondary sexual characteristics.
Used in Pharmaceutical Industry:
(3β,22S)-Dihydroxy Cholesterol is used as an intermediate in the synthesis of various pharmaceutical compounds, particularly those related to hormone therapy and the treatment of hormonal imbalances. Its role in the production of steroid hormones makes it a valuable component in the development of drugs targeting conditions such as adrenal insufficiency, congenital adrenal hyperplasia, and certain types of infertility.
Used in Research and Development:
(3β,22S)-Dihydroxy Cholesterol is used as a research tool for studying the metabolism of cholesterol and the biosynthesis of steroid hormones. It helps researchers understand the mechanisms involved in hormone production and can aid in the development of new therapies for hormone-related disorders. Additionally, it can be used to investigate the role of cholesterol metabolites in various physiological and pathological processes.

Upstream product

• 66007-52-1 <20R,22S>-3α,5-Cyclo-cholestane-6β,20,22-triol-6-methylether 
• 107-82-4 i-pentyl bromide 
• 1036954-89-8 (20R,22S)-3β-(tert-butyldimethylsilyl)oxycholest-5-ene-20,22-diol 
• 7154-75-8 4-methylpentyne 
• 145-13-1 Pregnenolone 
• 58701-45-4 3β-t-butyldimethylsilyloxy-pregn-5-en-20-one 
• 115910-64-0 (20R)-3β-(tert-butyldimethylsilyl)oxycholest-5-en-22-yn-20-ol 
• 782494-64-8 (20R,22Z)-3β-(tert-butyldimethylsilyl)oxycholesta-5,22-dien-20-ol 
• 782494-66-0 (20R,22S,23S)-22,23-epoxy-3β-(tert-butyldimethylsilyl)oxycholest-5-en-20-ol 
• 66007-50-9 (R)-1-((1aR,3aR,3bS,5aS,6S,8aS,8bS,10R,10aR)-10-Methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-1-(S)-oxiranyl-ethanol 

Relevant articles and documents

INHIBITION OF PPAR GAMMA EXPRESSION IN PREADIPOCYTE CELLS BY OXYSTEROLS

This invention relates, e.g., to methods and agents to inhibit peroxisome proliferator activated receptor expression (PPAR) in preadipocytes.

Studies on steroids. XLV. Synthesis of the four stereoisomers of 20,22 dihydroxycholesterol

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