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Merck

H5884

22(S)-Hydroxycholesterol

Sinónimos:

22β-Hydroxycholesterol, 5-Cholestene-3β,22(S)-diol

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Fórmula empírica (notación de Hill):
C27H46O2
Número CAS:
22348-64-7
Peso molecular:
402.65
NACRES:
NA.77
PubChem Substance ID:
24895715
UNSPSC Code:
12352211
MDL number:
MFCD00010476

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InChI

1S/C27H46O2/c1-17(2)6-11-25(29)18(3)22-9-10-23-21-8-7-19-16-20(28)12-14-26(19,4)24(21)13-15-27(22,23)5/h7,17-18,20-25,28-29H,6,8-16H2,1-5H3/t18-,20-,21-,22+,23-,24-,25-,26-,27+/m0/s1

SMILES string

[H][C@@]12[C@]([C@](CC[C@H](O)C3)(C)C3=CC2)([H])CC[C@@]4(C)[C@@]1([H])CC[C@]4([H])[C@]([H])(C)[C@@H](O)CCC(C)C

InChI key

RZPAXNJLEKLXNO-QUOSNDFLSA-N

assay

≥98% (TLC)

form

powder

shipped in

ambient

storage temp.

room temp

Quality Level

200

Categorías relacionadas

Application

Human hepatoma cells were treated with 22(S)-Hydroxycholesterol to study cholesterol modulation by liver X receptor-mediated gene regulation.

Biochem/physiol Actions

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 hepatocytes, myotubes and non-adipose tissue.

Preparation Note

22(S)-Hydroxycholesterol yields clear, colorless solution in chloroform at 20 mg/ml.

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificados de análisis (COA)

Lot/Batch Number
0000462387
0000462387
0000365890
0000365890
0000338462

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Eili Tranheim Kase et al.
Biochimica et biophysica acta, 1761(12), 1515-1522 (2006-10-24)
The nuclear liver X receptors (LXRalpha and beta) are regulators of lipid and cholesterol metabolism. Oxysterols are known LXR ligands, but the functional role of hydroxycholesterols is at present unknown. In human myotubes, chronic exposure to the LXR ligand T0901317
E T Kase et al.
Diabetologia, 50(10), 2171-2180 (2007-07-31)
Liver X receptors (LXRs) play important roles in lipid and carbohydrate metabolism. The purpose of the present study was to evaluate effects of the endogenous LXR agonist 22-R-hydroxycholesterol (22-R-HC) and its stereoisomer 22-S-hydroxycholesterol (22-S-HC), in comparison with the synthetic agonist
Lourdes Cruz-Garcia et al.
Comparative biochemistry and physiology. Part A, Molecular & integrative physiology, 160(2), 125-136 (2011-06-04)
The liver X receptor (LXR) has recently been described in salmonids. In mammals, this receptor is already known as a transcriptional factor that regulates diverse aspects of cholesterol, fatty acid and carbohydrate metabolism in various tissues, including muscle. Here we
R C Tuckey
The Journal of steroid biochemistry and molecular biology, 42(8), 883-890 (1992-09-01)
The side-chain cleavage of cholesterol by cytochrome P-450scc in mitochondria from the human placenta was studied using hydroxycholesterol substrates and intermediates of the reaction. 25-Hydroxycholesterol inhibited 3 beta-hydroxy-5-pregnen-20-one (pregnenolone) production by placental mitochondria. It was converted to pregnenolone at a
Tatsuhiko Adachi et al.
Molecular pharmaceutics, 6(6), 1678-1688 (2009-07-11)
Human ATP-binding cassette (ABC) transporter ABCC2 (cMOAT/MRP2) plays a crucial role in the hepatobiliary transport of sulfate-, glucuronide-, and glutathione-conjugated metabolites as well as a variety of amphiphilic organic anions derived from hepatic metabolism. Molecular mechanisms underlying the induction of
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