22(R)-HYDROXYCHOLESTEROL

22(R)-HYDROXYCHOLESTEROL
  • CAS No.:17954-98-2
Other grades of this product :
22(R)-HYDROXYCHOLESTEROL 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:17954-98-2
MF:C27H46O2
MW:402.65
EINECS:
Product Categories:Hydroxycholesterol;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Steroids
Mol File:17954-98-2.mol
22(R)-HYDROXYCHOLESTEROL Chemical Properties
Melting point 171-174°C
storage temp. -20°C
solubility Chloroform (Slightly), Methanol (Slightly)
form Solid
color White to Off-White
InChIKeyRZPAXNJLEKLXNO-QUOSNDFLSA-N
Safety Information
WGK Germany 3
MSDS Information
ProviderLanguage
SigmaAldrich English
22(R)-HYDROXYCHOLESTEROL Usage And Synthesis
DescriptionThe 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.
UsesThe 22R-metabolite of Cholesterol (C432501). 22-Hydroxycholesterol inhibits chemokine receptor activity.
UsesBovine 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.
DefinitionChEBI: An oxysterol that is the 22R-hydroxy derivative of cholesterol.
General Description22(R)-hydroxycholesterol is a diastereomer of 22(S)-hydroxycholesterol. It is present in neonate brain.
Biochem/physiol Actions22(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.
22(R)-HYDROXYCHOLESTEROL Preparation Products And Raw materials

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