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H5884

Sigma-Aldrich

22(S)-Hydroxycholesterol

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C27H46O2
Numéro CAS:
22348-64-7
Poids moléculaire :
402.65
Numéro MDL:
MFCD00010476
Code UNSPSC :
12352211
ID de substance PubChem :
24895715
Nomenclature NACRES :
NA.77

Pureté

≥98% (TLC)

Niveau de qualité

200

Forme

powder

Conditions d'expédition

ambient

Température de stockage

room temp

Chaîne SMILES 

[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

Clé InChI

RZPAXNJLEKLXNO-QUOSNDFLSA-N

Application

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

Actions biochimiques/physiologiques

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.

Notes préparatoires

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

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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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
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
Bassam Haidar et al.
The Journal of biological chemistry, 279(11), 9963-9969 (2004-01-01)
It has been suggested that the signal transduction pathway initiated by apoA-I activates key proteins involved in cellular lipid efflux. We investigated apoA-I-mediated cAMP signaling in cultured human fibroblasts induced with (22R)-hydroxycholesterol and 9-cis-retinoic acid (stimulated cells). Treatment of stimulated
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
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