Skip to Content
Merck
All Photos(2)

Key Documents

View All Documentation

Safety Information

700058P

Avanti

22(R)-hydroxycholesterol

Avanti Research™ - A Croda Brand

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(2)

About This Item

Empirical Formula (Hill Notation):
C27H46O2
CAS Number:
17954-98-2
Molecular Weight:
402.65
UNSPSC Code:
12352211
NACRES:
NA.25

description

cholest-5-ene-3β,22(R)-diol

Assay

>99% (TLC)

form

powder

packaging

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

manufacturer/tradename

Avanti Research™ - A Croda Brand

shipped in

dry ice

storage temp.

−20°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-GFKLAVDKSA-N

General description

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

Application

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.

Biochem/physiol Actions

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.

Packaging

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

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

700058P-5MG:
700058P-BULK:
700058P-VAR:
700058P-1MG:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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
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
Samantha A Hutchinson et al.
Nutrients, 11(11) (2019-11-07)
Interventions that alter cholesterol have differential impacts on hormone receptor positive- and negative-breast cancer risk and prognosis. This implies differential regulation or response to cholesterol within different breast cancer subtypes. We evaluated differences in side-chain hydroxycholesterol and liver X nuclear
Michael E Abrams et al.
Nature microbiology, 5(7), 929-942 (2020-04-15)
Cholesterol 25-hydroxylase (CH25H) is an interferon-stimulated gene that converts cholesterol to the oxysterol 25-hydroxycholesterol (25HC). Circulating 25HC modulates essential immunological processes including antiviral immunity, inflammasome activation and antibody class switching; and dysregulation of CH25H may contribute to chronic inflammatory disease
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service