22(R)-HYDROXYCHOLESTEROL Chemical Properties

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

InChIKey

RZPAXNJLEKLXNO-QUOSNDFLSA-N

Safety Information

WGK Germany 

3

MSDS

• Language:English Provider:SigmaAldrich

22(R)-HYDROXYCHOLESTEROL Usage And Synthesis

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

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

Uses

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.

References

[1] THOMAS A. SPENCER. Pharmacophore Analysis of the Nuclear Oxysterol Receptor LXRα[J]. Journal of Medicinal Chemistry, 2001, 44 6: 886-897. DOI: 10.1021/jm0004749
[2] P COSTET. Sterol-dependent transactivation of the ABC1 promoter by the liver X receptor/retinoid X receptor.[J]. The Journal of Biological Chemistry, 2000, 275 36: 28240-28245. DOI: 10.1074/jbc.m003337200
[3] XINYI WANG. Scopine as a Novel Brain-Targeting Moiety Enhances the Brain Uptake of Chlorambucil[J]. Bioconjugate Chemistry Bioconjugate, 2014, 25 11: 2046-2054. DOI: 10.1021/bc5004108

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