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HomeProduct name list22(R)-HYDROXYCHOLESTEROL

22(R)-HYDROXYCHOLESTEROL

Synonym(s):22α-Hydroxycholesterol;5-Cholestene-3β,22(R)-diol;5-Cholestene-3β,22[R]-diol;5-cholestene-3β,22-diol; 22-hydroxycholest-5-en-3-ol

22(R)-HYDROXYCHOLESTEROL Structural

What is 22(R)-HYDROXYCHOLESTEROL?

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.

The Uses of 22(R)-HYDROXYCHOLESTEROL

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.

The Uses of 22(R)-HYDROXYCHOLESTEROL

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

What are the applications of Application

22(R)-hydroxycholesterol is an endogenous LXR agonist

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.

Properties of 22(R)-HYDROXYCHOLESTEROL

Melting point: 171-174°C
Boiling point: 513.1±23.0 °C(Predicted)
Density  1.03±0.1 g/cm3(Predicted)
storage temp.  -20°C
solubility  Chloroform (Slightly), Methanol (Slightly)
form  Solid
pka 15.01±0.20(Predicted)
color  White to Off-White

Safety information for 22(R)-HYDROXYCHOLESTEROL

Computed Descriptors for 22(R)-HYDROXYCHOLESTEROL

InChIKey RZPAXNJLEKLXNO-QUOSNDFLSA-N

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