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700057P

Avanti

22(S)-hydroxycholesterol

Avanti Polar Lipids

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C27H46O2
CAS Number:
22348-64-7
Molecular Weight:
402.65
UNSPSC Code:
12352211
NACRES:
NA.25

description

cholest-5-ene-3β,22(S)-diol

Assay

>99% (TLC)

form

powder

packaging

pkg of 1 × 5 mg (700057P-5mg)

manufacturer/tradename

Avanti Polar Lipids

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-QUOSNDFLSA-N

General description

22(S)-hydroxycholesterol is a stereo isoform of the 22(R)-hydroxycholesterol.

Biochem/physiol Actions

22(S)-hydroxycholesterol (22(S)-HC) promotes glucose catabolism and uptake. It is regarded as a potential target to treat type 2 diabetes. 22(S)-HC also prevents the accumulation of lipids and lipid synthesis in hepatocytes and myotubes. It shows no interaction with liver X receptor (LXR) like 22(R)-hydroxycholesterol and is not estrogenic.

Packaging

5 mL Amber Glass Screw Cap Vial (700057P-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

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’.

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Ying Liu et al.
Journal of lipid research, 59(3), 439-451 (2018-01-05)
Cholesterol 25-hydroxylase (CH25H) catalyzes the production of 25-hydroxycholesterol (25-HC), an oxysterol that can play an important role in different biological processes. However, the mechanisms regulating CH25H expression have not been fully elucidated. In this study, we determined that CH25H is
Hiroyoshi Sato et al.
Bioscience, biotechnology, and biochemistry, 68(8), 1790-1793 (2004-08-24)
In order to test the estrogenic activity of sterol oxidation products from cholesterol and phytosterols, an estrogen-dependent gene expression assay was performed in estrogen receptor alpha-stably transformed HeLa cells. The ranking of the estrogenic potency of these compounds was different:

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