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

The liver X receptors (LXRα and LXRβ) are nuclear hormone receptors whose native ligands are oxysterols. LXRs regulate the oxysterol-induced expression of cholesterol 7α-hydroxylase, the rate limiting enzyme of classic bile acid synthesis. 22(R)-hydroxy Cholesterol is an endogenous agonist for LXRs that activates LXRα with an EC50 value of 325 nM. 22(R)-hydroxy Cholesterol, 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. 22(R)-hydroxy Cholesterol can be used as a substrate to monitor cholesterol transport or as an endogenous positive control for testing LXR agonists which have potential as therapeutic agents for the treatment of atherosclerosis.

Uses

Different sources of media describe the Uses of 17954-98-2 differently. You can refer to the following data:
1. The 22R-metabolite of Cholesterol (C432501). 22-Hydroxycholesterol inhibits chemokine receptor activity.
2. Bovine aortic endothelial cells were treated with 22(R)-Hydroxycholesterol to study the effects on production of free radicals and in studies related to fatty acid metabolism.

Definition

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

General Description

22(R)-hydroxycholesterol is a diastereomer of 22(S)-hydroxycholesterol. It is present in neonate brain.

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

• 32277-72-8 3β-acetoxy-cholest-5-en-22-one 
• 57-88-5 cholesterol 
• 66702-96-3 (E)-1-iodo-3-methylbut-1-ene 
• 70813-75-1 (E)-(3-methylbut-1-en-1-yl)boronic acid 
• 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 
• 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 

Downstream Products

• 54604-57-8 (22S)-cholest-5-ene-3β,22-diol 3β-acetate 
• 110536-30-6 22-fluoroprevitamin D₃ 
• 110536-31-7 22-fluorovitamin D₃ 
• 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 
• 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.