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H9384

Sigma-Aldrich

22(R)-Hydroxycholesterol

≥98%

Sinónimos:

22α-Hydroxycholesterol, 5-Cholestene-3β,22(R)-diol, 5-Cholestene-3β,22[R]-diol

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About This Item

Fórmula empírica (notación de Hill):
C27H46O2
Número de CAS:
17954-98-2
Peso molecular:
402.65
Número MDL:
MFCD00070042
Código UNSPSC:
12352211
eCl@ss:
39023139
ID de la sustancia en PubChem:
24895852
NACRES:
NA.77

Nivel de calidad

200

Análisis

≥98%

formulario

powder

Condiciones de envío

ambient

temp. de almacenamiento

room temp

cadena SMILES

[H][C@@]12CC=C3C[C@@H](O)CC[C@]3(C)[C@@]1([H])CC[C@]4(C)[C@H](CC[C@@]24[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

Clave InChI

RZPAXNJLEKLXNO-GFKLAVDKSA-N

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Aplicación

Bovine aortic endothelial cells were treated with 22(R)-Hydroxycholesterol to study the effects on production of free radicals and in studies related to fatty acid metabolism.

Acciones bioquímicas o fisiológicas

22(R)-Hydroxycholesterol is an intermediate of the pregnenolone synthesis pathway from cholesterol. It reported has neuroprotective properties and protects the neurons against β-amyloid-induced cell death. 22(R)-Hydroxycholesterol acts as the ligand of liver X receptors that act as sensors of sterol concentration and regulates the fatty acid metabolism.

Nota de preparación

22(R)-Hydroxycholesterol yield clear, colorless solution in chloroform.

Producto relacionado

Referencia del producto
Descripción
Precios

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

Eyeshields, Gloves, type N95 (US)

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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A Chawla et al.
Science (New York, N.Y.), 294(5548), 1866-1870 (2001-12-01)
Cholesterol, fatty acids, fat-soluble vitamins, and other lipids present in our diets are not only nutritionally important but serve as precursors for ligands that bind to receptors in the nucleus. To become biologically active, these lipids must first be absorbed
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
Cynthia Hong et al.
Journal of lipid research, 52(3), 531-539 (2010-12-29)
Ligand activation of liver X receptors (LXRs) has been shown to impact both lipid metabolism and inflammation. One complicating factor in studies utilizing synthetic LXR agonists is the potential for pharmacologic and receptor-independent effects. Here, we describe an LXR gain-of-function
Kosuke Dodo et al.
Bioorganic & medicinal chemistry, 16(8), 4272-4285 (2008-03-18)
Liver X receptors (LXR), which were originally reported as oxysterol-activated nuclear receptors, were recently found to recognize glucose as a physiological ligand. On this basis, we have already developed novel LXR antagonists based upon alpha-glucosidase inhibitors derived from thalidomide. Here
I L M H Aye et al.
Placenta, 32(2), 183-191 (2011-01-07)
Oxygenated cholesterol metabolites known as oxysterols display potent biological activities ranging from regulation of lipid homeostasis to cytotoxicity. Oxysterols have previously been shown to inhibit the invasion of first trimester trophoblasts, an effect which involves activation of the nuclear liver
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