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H5884

Sigma-Aldrich

22(S)-Hydroxycholesterol

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C27H46O2
CAS-Nummer:
22348-64-7
Molekulargewicht:
402.65
MDL-Nummer:
MFCD00010476
UNSPSC-Code:
12352211
PubChem Substanz-ID:
24895715
NACRES:
NA.77

Assay

≥98% (TLC)

Qualitätsniveau

200

Form

powder

Versandbedingung

ambient

Lagertemp.

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

InChIKey

RZPAXNJLEKLXNO-QUOSNDFLSA-N

Verwandte Kategorien

Anwendung

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

Biochem./physiol. Wirkung

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.

Angaben zur Herstellung

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

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)

Analysenzertifikate (COA)

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Sigma-Aldrich

C8003

5-α-Cholestan

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Sigma-Aldrich

C2394

5-Cholesten-3β-ol-7-on

GW3965 hydrochloride ≥98% (HPLC), powder

Sigma-Aldrich

G6295

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Cholesterin Sigma Grade, ≥99%

Sigma-Aldrich

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Cholesterin

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
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
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
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
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