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700058P

Avanti

22(R)-hydroxycholesterol

Avanti Research™ - A Croda Brand

Sinónimos:

5-cholestene-3β,22-diol; 22-hydroxycholest-5-en-3-ol

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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
NACRES:
NA.25

descripción

cholest-5-ene-3β,22(R)-diol

Ensayo

>99% (TLC)

Formulario

powder

envase

pkg of 1 × 1 mg (700058P-1mg)
pkg of 1 × 5 mg (700058P-5mg)

fabricante / nombre comercial

Avanti Research™ - A Croda Brand

Condiciones de envío

dry ice

temp. de almacenamiento

−20°C

cadena SMILES

O[C@H]1CC[C@@]2([C@@H]3[C@H]([C@H]4[C@@]([C@H](CC4)[C@@H]([C@H](O)CCC(C)C)C)(CC3)C)CC=C2C1)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

Descripción general

22(R)-hydroxycholesterol is a diastereomer of 22(S)-hydroxycholesterol. It is present in neonate brain.

Aplicación

22(R)-hydroxycholesterol has been used as a liver X receptor (LXR) ligand in breast cancer cell lines. It may be used as an internal standard to spike mouse brain tissue samples for ultra-performance liquid chromatography–high resolution mass spectrometry (UPLC-ESI-HRMS) analysis.

Acciones bioquímicas o fisiológicas

22(R)-hydroxycholesterol (22(R)-HC) is a liver X receptor (LXR) ligand.. 22(R)-HC in combination with other oxysterols promote mesenchymal stem cell osteogenesis. It regulates cholesterol homeostasis. Low levels of 22(R)-HC is observed in Alzheimer′s disease and it may be implicated in neuroinflammation and neurodegenerative diseases. 22(R)-hydroxycholesterol also suppresses prostate tumor progression.

Envase

5 mL Amber Glass Screw Cap Vial (700058P-1mg)
5 mL Amber Glass Screw Cap Vial (700058P-5mg)

Información legal

Avanti Research is a trademark of Avanti Polar Lipids, LLC

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

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Certificados de análisis (COA)

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Sophie Ayciriex et al.
Analytical and bioanalytical chemistry, 404(10), 3049-3059 (2012-09-27)
Cholesterol and oxysterols are involved as key compounds in the development of severe neurodegenerative diseases and in neuroinflammation processes. Monitoring their concentration changes under pathological conditions is of interest to get insights into the role of lipids in diseases. For
Megan M Augustin et al.
The Plant journal : for cell and molecular biology, 82(6), 991-1003 (2015-05-06)
Steroid alkaloids have been shown to elicit a wide range of pharmacological effects that include anticancer and antifungal activities. Understanding the biosynthesis of these molecules is essential to bioengineering for sustainable production. Herein, we investigate the biosynthetic pathway to cyclopamine
Combined treatment with 9-cis beta-carotene and 22R-hydroxycholesterol augments cholesterol efflux in macrophages
Mahler L, et al.
Algal research, 44, 101700-101700 (2019)
Hyunmi Kim et al.
Biochimica et biophysica acta, 1859(8), 1056-1070 (2016-05-22)
MAP kinase phosphatase (MKP)-1 plays a pivotal role in controlling MAP kinase (MAPK)-dependent (patho) physiological processes. Although MKP-1 gene expression is tightly regulated at multiple levels, the underlying mechanistic details remain largely unknown. In this study, we demonstrate that MKP-1
Fatemeh Hassani-Nezhad-Gashti et al.
Clinical pharmacology and therapeutics, 108(4), 856-865 (2020-04-29)
We conducted a clinical trial with 22 healthy volunteers to investigate the effects of pregnane X receptor (PXR) agonist rifampin on blood pressure (BP). The study was randomized, crossover, single-blind, and placebo-controlled. Rifampin 600 mg or placebo once daily was administered
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