ChemicalBook--->CAS DataBase List--->22348-64-7

22348-64-7

22348-64-7 Structure

22348-64-7 Structure
IdentificationBack Directory
[Name]

22(R)-HYDROXYCHOLESTEROL
[CAS]

22348-64-7
[Synonyms]

C05502
22(R)-OH-CH
22BF-HYDROXYCHOLESTEROL
22β-Hydroxy Cholesterol
22(S)-HYDROXYCHOLESTEROL
22BETA-HYDROXYCHOLESTEROL
(5-Cholestene-322(S)-diol)
22-HYDROXYCHOLESTEROL (22R)
22-ALPHA-HYDROXYCHOLESTEROL
Cholest-5-ene-3β,22(S)-diol
(22S)-22-Hydroxycholesterol
CHOLEST-5-ENE-3BETA,22R-DIOL
5-CHOLESTENE-3BETA,22[R]-DIOL
5-CHOLESTENE-3BETA,22[S]-DIOL
5-CHOLESTEN-3-BETA, 22(R)-DIOL
5-CHOLESTEN-3-BETA, 22(S)-DIOL
22ALPHA-DIHYDROXY-5-CHOLESTENE
(22S)-Cholest-5-ene-3β,22-diol
(3β,22S)-Cholest-5-ene-3,22-diol
(20S,22S)-Cholest-5-ene-3β,22-diol
Cholest-5-ene-3,22-diol, (3β,22S)-
3BETA,22BETA-DIHYDROXY-5-CHOLESTENE
22[S]-Hydroxycholesterol (not deuterated)
22β-Hydroxycholesterol, 5-Cholestene-3β,22(S)-diol
CHOLEST-5-ENE-3,22(S)-DIOL;22(S)-HYDROXYCHOLESTEROL
(3S,8S,9S,10R,13R,14S,17R)-17-[(2S,3R)-3-hydroxy-6-methyl-heptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
[Molecular Formula]

C27H46O2
[MDL Number]

MFCD00010476
[MOL File]

22348-64-7.mol
[Molecular Weight]

402.65
Chemical PropertiesBack Directory
[storage temp. ]

Store at -20°C
[solubility ]

DMF: 2 mg/ml; DMSO: 0.1 mg/ml; Ethanol: 20 mg/ml; Ethanol:PBS (pH 7.2)(1:2): 0.3 mg/ml
[form ]

A crystalline solid
[InChIKey]

RZPAXNJLEKLXNO-QUOSNDFLSA-N
[SMILES]

O[C@H]1CC[C@@]2([C@@H]3[C@H]([C@H]4[C@@]([C@H](CC4)[C@@H]([C@@H](O)CCC(C)C)C)(CC3)C)CC=C2C1)C
Safety DataBack Directory
[WGK Germany ]

3
[Storage Class]

11 - Combustible Solids
Hazard InformationBack Directory
[Uses]

The 22S-metabolite of Cholesterol (C432501). 22-Hydroxycholesterol inhibits chemokine receptor activity.
[Definition]

ChEBI: An oxysterol that is the 22S-hydroxy derivative of cholesterol.
[Biological Activity]

22(S)-Hydroxycholesterol modulates the lipid and glucose metabolism by acting on liver X receptors. It has the potential to reduce lipogenesis and the accumulation of lipid in hepatocytesmyotubes and non-adipose tissue.
[in vivo]

Cholest-5-ene-3?,22(S)-diol (30 mg/kg; p.o.; added in diet, treated for 3 weeks) reduces body weight gain and abolishes high-fat diet-induced increase of triacylglycerol (TAG) levels in serum[2].

Pharmacokinetic Analysis in Rats[2]

RouteDose (mg/kg)Cmax (ng/mL)Tmax (h)AUCt (ng·h/mL)AUC (ng·h/mL)T1/2 (h)Extent of tritium exchange (%)
i.v.5022.40.081741958.12.8
p.o.507.5495.21046.41.2
Animal Model:Male rats injected with Pentobarbital (20 mg, 50 mg/mL; i.p.)[2]
Dosage:30 mg/kg/day
Administration:Oral gavage; 3 weeks consecutively
Result:Decreased body weight gain significantly after 1 week treatment.
Increased gene expression of Ucp3 and Cpt2 in liver and skeletal muscle, and increased protein level of Ucp3 in skeletal muscle after 3 weeks treatment.
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