H5884
22(S)-Hydroxycholesterol
Synonym(s):
22β-Hydroxycholesterol, 5-Cholestene-3β,22(S)-diol
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About This Item
Empirical Formula (Hill Notation):
C27H46O2
CAS Number:
Molecular Weight:
402.65
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352211
MDL number:
assay
≥98% (TLC)
Quality Level
form
powder
shipped in
ambient
storage temp.
room temp
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
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
InChI key
RZPAXNJLEKLXNO-QUOSNDFLSA-N
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.
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Storage Class
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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B A Laffitte et al.
Molecular and cellular biology, 21(22), 7558-7568 (2001-10-18)
Previous work has implicated the nuclear receptors liver X receptor alpha (LXR alpha) and LXR beta in the regulation of macrophage gene expression in response to oxidized lipids. Macrophage lipid loading leads to ligand activation of LXRs and to induction
K Hanley et al.
The Journal of investigative dermatology, 114(3), 545-553 (2000-02-26)
Ligands and activators of the nuclear hormone receptor superfamily are important in the regulation of epidermal development and differentiation. Previously, we showed that naturally occurring fatty acids, as well as synthetic ligands for the peroxisome proliferator-activated receptor, induce keratinocyte differentiation
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
Global Trade Item Number
| SKU | GTIN |
|---|---|
| H5884-10MG | 04061833799895 |
| H5884-5MG | 04061833076507 |