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| | 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 | | 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 | | SMILES | [H][C@@]12CC=C3C[C@@H](O)CC[C@]3(C)[C@@]1([H])CC[C@]4(C)[C@H](CC[C@@]24[H])[C@H](C)[C@H](O)CCC(C)C |
| WGK Germany | 3 | | Storage Class | 11 - Combustible Solids |
| | 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 |
| | 22(R)-HYDROXYCHOLESTEROL Preparation Products And Raw materials |
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