22348-64-7

Basic information

• Product Name: 22(R)-HYDROXYCHOLESTEROL
• Synonyms: 22(S)-HYDROXYCHOLESTEROL;22(R)-OH-CH;22BETA-HYDROXYCHOLESTEROL;22BF-HYDROXYCHOLESTEROL;22-HYDROXYCHOLESTEROL (22R);22ALPHA-DIHYDROXY-5-CHOLESTENE;22-ALPHA-HYDROXYCHOLESTEROL;5-CHOLESTENE-3BETA,22[R]-DIOL
• CAS NO: 22348-64-7
• Molecular Formula: C₂₇H₄₆O₂
• Molecular Weight: 402.65
• Product Categories: Hydroxycholesterol;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Steroids
• Mol File: 22348-64-7.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 513.1 °C at 760 mmHg
• Flash Point: 213.5 °C
• Appearance: /
• Density: 1.03 g/cm³
• Vapor Pressure: 1.13E-12mmHg at 25°C
• Refractive Index: 1.536
• CAS DataBase Reference: 22(R)-HYDROXYCHOLESTEROL(CAS DataBase Reference)
• NIST Chemistry Reference: 22(R)-HYDROXYCHOLESTEROL(22348-64-7)
• EPA Substance Registry System: 22(R)-HYDROXYCHOLESTEROL(22348-64-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 22348-64-7(Hazardous Substances Data)

Usage

Uses

The 22S-metabolite of Cholesterol (C432501). 22-Hydroxycholesterol inhibits chemokine receptor activity.

Definition

ChEBI: An oxysterol that is the 22S-hydroxy derivative of cholesterol.

InChI:InChI=1/C27H46O2/c1-17(2)6-11-25(29)18(3)22-9-10-23-21-8-7-19-16-20(28)12-14-26(19,4)24(21)13-15-27(22,23)5/h7,17-18,20-25,28-29H,6,8-16H2,1-5H3/t18-,20-,21-,22+,23-,24-,25-,26-,27+/m0/s1

Upstream product

• 32277-72-8 3β-acetoxy-cholest-5-en-22-one 
• 69454-88-2 3β-((tert-butyldimethylsilyl)oxy)-22-hydroxy-23,24-bisn-orchol-5-en 
• 69454-87-1 (3β,20S)-3-<(tert-butyldimethylsilyl)oxy>pregn-5-ene-20-carboxylic acidmethyl ester 
• 10527-79-4 methyl 3β-hydroxy-23-bisnorchol-5-en-22-oate 
• 4548-78-1 (3-methylbutyl)magnesium bromide 
• 566-77-8 hydroxybisnorcholenic acid 
• 140659-51-4 (2β,20S)-3-<(tert-butyldimethylsilyl)oxy>pregn-5-ene-20-carboxaldehyde 
• 70813-75-1 (E)-(3-methylbut-1-en-1-yl)boronic acid 
• 66702-96-3 (E)-1-iodo-3-methylbut-1-ene 
• 128292-36-4 (1-Bromo-4-methyl-pentyl)-[(3S,8R,9S,10R,13S,14S,16R)-17-eth-(E)-ylidene-10,13-dimethyl-3-(tetrahydro-pyran-2-yloxy)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-16-yloxy]-dimethyl-silane 
• 128292-42-2 (2S,4aR,4bS,6aS,6bR,7S,8R,10aR,11aS,11bS)-4a,6a,7,9-Tetramethyl-8-(3-methyl-butyl)-2-(tetrahydro-pyran-2-yloxy)-1,2,3,4,4a,4b,5,6,6a,6b,7,8,9,10a,11,11a,11b,12-octadecahydro-10-oxa-9-sila-indeno[2,1-a]phenanthren-9-ol 
• 128292-38-6 (3S,8S,9S,10R,13S,14S,16R,17R)-17-((1S,2R)-2-Hydroxy-1,5-dimethyl-hexyl)-10,13-dimethyl-3-(tetrahydro-pyran-2-yloxy)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-16-ol 
• 128383-32-4 (1-Bromo-4-methyl-pentyl)-dimethyl-phenyl-silane 
• 128292-39-7 Dimethyl-((E)-4-methyl-pent-1-enyl)-phenyl-silane 

Downstream Products

• 54548-85-5 (20(22)E)-cholesta-5,20(22)-dien-3β-ol acetate 
• 110536-31-7 22-fluorovitamin D₃ 
• 110536-30-6 22-fluoroprevitamin D₃ 
• 54604-57-8 (22S)-cholest-5-ene-3β,22-diol 3β-acetate 
• 17955-01-0 (22S)-22-hydroxycholesterol dibenzoate 

Relevant articles and documents

Regulation of liver X receptor target genes by 22-functionalized oxysterols. Synthesis, in silico and in vitro evaluations

The endogenous oxysterol 22(R)-hydroxycholesterol (22RHC, 1) is an LXR agonist which upregulates genes of critical involvement in human cholesterol- and lipid metabolism. In contrast, its synthetic epimer 22(S)-hydroxycholesterol (22SHC, 8) has shown specific antagonistic effects in recent studies, avoiding unwanted side effects provided by potent LXR agonists. In terms of LXR modulation, the aim of this study was to compare 22SHC (8), 22RHC (1) and synthesized ligands with keto- and amide functionality in the 22nd position of the cholesterol scaffold. 22SHC (8) and 22RHC (1) performed as expected while 22-ketocholesterol (22KC, 10) revealed an attractive in vitro profile for further investigation in terms of anti-atherosclerotic properties as selective upregulation of the ATP-binding cassette transporter ABCA1 was observed. A new synthesized amide derivate, Fernholtz cyclohexylamide (13) was shown to reduce lipogenesis in a dose-responsive manner and abolish the effect of the potent LXR agonist T0901317 when administered simultaneously.

Stereocontrolled Synthesis of (22R)-22-Hydroxycholesterol Guided by α-Silyl Radical Stabilization

The synthesis of (22R)-22-hydroxycholesterol, featuring formation of three contiguous chiral centers (C-17, 20, and 22) in a single step by the use of a 6-endo α-silyl radical-mediated cyclization is presented.Additionally, an interesting protiodesilyatio

Stereoselective Synthesis of Plant Growth-promoting Steroids, Brassinolide, Castasterone, Typhasterol, and Their 28-Nor Analogues

Plant growth-promoting steroids, brassinolide (1a), (22R,23R,24S)-2α,3α,22,23-tetrahydroxy-B-homo-7-oxa-5α-ergostan-6-one, castasterone (2a), (22R,23R,24S)-2α,3α,22,23-tetrahydroxy-5α-ergostan-6-one, 28-norbrassinolide (1b), (22R,23R)-2α,3α,22,23-tetrahydroxy-B-homo-7-oxa-5α-cholestan-6-one, brassinone (2b), (22R,23R)-2α,3α,22,23-tetrahydroxy-5α-cholestan-6-one, and typhasterol (2c), (22R,23R,24S)-3α,22,23-trihydroxy-5α-ergostan-6-one, have been stereoselectively synthesized.These steroids show very strong biological activities in three different kinds of bioassays.