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H5884

22(S)-Hydroxycholesterol

Name: 22(S)-Hydroxycholesterol
Brand: SIGMA

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):

C₂₇H₄₆O₂

CAS Number:

22348-64-7

Molecular Weight:

402.65

NACRES:

NA.77

PubChem Substance ID:

24895715

UNSPSC Code:

12352211

MDL number:

MFCD00010476

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assay

≥98% (TLC)

Quality Level

200

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

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Biochemicals

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.

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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Certificates of Analysis (COA)

Lot/Batch Number

0000462387

0000365890

0000338462

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Liver X receptor antagonist reduces lipid formation and increases glucose metabolism in myotubes from lean, obese and type 2 diabetic individuals.

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

22-Hydroxycholesterols regulate lipid metabolism differently than T0901317 in human myotubes.

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

Autoregulation of the human liver X receptor alpha promoter.

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

Oxysterols induce differentiation in human keratinocytes and increase Ap-1-dependent involucrin transcription.

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

Cholesterol side-chain cleavage by mitochondria from the human placenta. Studies using hydroxycholesterols as substrates.

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

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Global Trade Item Number

SKU	GTIN
H5884-5MG	04061833076507
H5884-10MG	04061833799895

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