| Identification | Back Directory | [Name]
22(R)-HYDROXYCHOLESTEROL | [CAS]
17954-98-2 | [Synonyms]
22R-OHC
22(R)-OH-CH
Narthesterol
22α-hydroxycholesterol
Cholesterol 22α-Hydroxy
22α-Hydroxy Cholesterol
22BF-HYDROXYCHOLESTEROL
22(R)-HYDROXYCHOLESTEROL
22BETA-HYDROXYCHOLESTEROL
5-Cholestene-3β,22(R)-diol
5-Cholestene-3β,22[R]-diol
Cholest-5-ene-3β,22(R)-diol
22-ALPHA-HYDROXYCHOLESTEROL
22-HYDROXYCHOLESTEROL (22R)
CHOLEST-5-ENE-3BETA,22R-DIOL
5-CHOLESTENE-3BETA,22[R]-DIOL
5-CHOLESTEN-3-BETA, 22(R)-DIOL
(22R)-Cholest-5-ene-3β,22-diol
(3β,22R)-Cholest-5-ene-3,22-diol
(20S,22R)-Cholest-5-ene-3β,22-diol
(3beta,22R)-Cholest-5-ene-3,22-diol
3BETA,22BETA-DIHYDROXY-5-CHOLESTENE
Cholest-5-ene-3,22-diol, (3beta,22R)-
22[R]-Hydroxycholesterol (not deuterated)
(22a-Hydroxycholesterol, 5-Cholestene-322(R)-diol)
22α-Hydroxycholesterol, 5-Cholestene-3β,22(R)-diol, 5-Cholestene-3β,22[R]-diol | [Molecular Formula]
C27H46O2 | [MDL Number]
MFCD00070042 | [MOL File]
17954-98-2.mol | [Molecular Weight]
402.65 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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]
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. | [Uses]
The 22R-metabolite of Cholesterol (C432501). 22-Hydroxycholesterol inhibits chemokine receptor activity. | [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. | [storage]
Store at -20°C | [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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