17954-98-2

Basic information

• Product Name: 22(R)-HYDROXYCHOLESTEROL
• Synonyms: 22α-Hydroxycholesterol, 5-Cholestene-3β,22(R)-diol, 5-Cholestene-3β,22[R]-diol;(22R)-Cholest-5-ene-3β,22-diol;22R-OHC;(3beta,22R)-Cholest-5-ene-3,22-diol;Cholest-5-ene-3,22-diol, (3beta,22R)-;(20S,22R)-Cholest-5-ene-3β,22-diol;(3β,22R)-Cholest-5-ene-3,22-diol;Cholest-5-ene-3β,22(R)-diol
• CAS NO: 17954-98-2
• Molecular Formula: C₂₇H₄₆O₂
• Molecular Weight: 402.65
• Product Categories: Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Steroids;Hydroxycholesterol
• Mol File: 17954-98-2.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 513.1 °C at 760 mmHg
• Flash Point: 213.5 °C
• Appearance: /
• Density: 1.03 g/cm³
• Refractive Index: 1.536
• Storage Temp.: -20°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 22(R)-HYDROXYCHOLESTEROL(CAS DataBase Reference)
• NIST Chemistry Reference: 22(R)-HYDROXYCHOLESTEROL(17954-98-2)
• EPA Substance Registry System: 22(R)-HYDROXYCHOLESTEROL(17954-98-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 17954-98-2(Hazardous Substances Data)

Usage

Description

22(R)-Hydroxycholesterol, also known as the 22R-metabolite of cholesterol, is an oxysterol that is the 22R-hydroxy derivative of cholesterol. It is an endogenous agonist for liver X receptors (LXRα and LXRβ), which are nuclear hormone receptors that regulate the expression of cholesterol 7α-hydroxylase, the rate-limiting enzyme of classic bile acid synthesis. 22(R)-Hydroxycholesterol is present in neonate brain and can be used as a substrate to monitor cholesterol transport or as an endogenous positive control for testing LXR agonists.

Uses

Used in Cellular and Metabolic Studies:
22(R)-Hydroxycholesterol is used as a research tool for studying the effects on the production of free radicals and in studies related to fatty acid metabolism in bovine aortic endothelial cells.
Used in Chemokine Receptor Inhibition:
22(R)-Hydroxycholesterol is used as an inhibitor of chemokine receptor activity, which can be relevant for various biological and medical applications.
Used in Cholesterol Transport and Absorption:
22(R)-Hydroxycholesterol, acting through LXR heterodimerized with the retinoid X receptor, induces the expression of the ABCA1 reverse cholesterol transporter. This activity increases the efflux of cholesterol from enterocytes and thus inhibits the overall absorption of cholesterol, making it potentially useful in the treatment of atherosclerosis and other cholesterol-related conditions.
Used in Drug Development:
22(R)-Hydroxycholesterol can be used as an endogenous positive control for testing LXR agonists, which have potential as therapeutic agents for the treatment of atherosclerosis and other diseases associated with cholesterol metabolism dysregulation.

Biochem/physiol Actions

22(R)-hydroxycholesterol (22(R)-HC) is a liver X receptor (LXR) ligand.. 22(R)-HC in combination with other oxysterols promote mesenchymal stem cell osteogenesis. It regulates cholesterol homeostasis. Low levels of 22(R)-HC is observed in Alzheimer′s disease and it may be implicated in neuroinflammation and neurodegenerative diseases. 22(R)-hydroxycholesterol also suppresses prostate tumor progression.

InChI:InChI=1/C27H46O2/c1-17(2)7-6-8-18(3)22-11-12-23-21-10-9-19-15-20(28)16-25(29)27(19,5)24(21)13-14-26(22,23)4/h9,17-18,20-25,28-29H,6-8,10-16H2,1-5H3/t18-,20-,21+,22-,23+,24+,25?,26-,27+/m1/s1

Upstream product

• 76719-31-8 2-{(3S,8S,9S,10R,13S,14S,17R)-17-[1-((2S,3S)-3-Isobutyl-oxiranyl)-ethyl]-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxy}-tetrahydro-pyran 
• 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 
• 128292-37-5 (2S,4aR,4bS,6aS,6bR,7S,8R,10aR,11aS,11bS)-4a,6a,7,9,9-Pentamethyl-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]phenanthrene 
• 128292-46-6 C₄₁H₆₂O₇S 
• 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 

Downstream Products

• 54548-85-5 (20(22)E)-cholesta-5,20(22)-dien-3β-ol acetate 
• 20117-31-1 3β,22β_F-bis-benzoyloxy-5α-cholestane 
• 62698-12-8 3β-benzoyloxy-cholesta-5,20(22)t-diene 
• 481-21-0 cholestane 
• 110536-31-7 22-fluorovitamin D₃ 
• 110536-30-6 22-fluoroprevitamin D₃ 
• 54604-57-8 (22S)-cholest-5-ene-3β,22-diol 3β-acetate 
• 145-13-1 Pregnenolone 
• 15234-55-6 (22R)-20α,22-dihydroxycholesterol 
• 17955-01-0 (22S)-22-hydroxycholesterol dibenzoate 
• 17955-00-9 3β,22β_F-bis-benzoyloxy-cholest-5-ene 
• 19243-30-2 22-ketocholesterol 

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.