700127P
Avanti
7-keto-25-hydroxycholesterol
3β,25-dihydroxy-5-cholesten-7-one, powder
Synonym(s):
cholest-5-ene-7-one-3β,25-diol
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About This Item
Empirical Formula (Hill Notation):
C27H44O3
CAS Number:
Molecular Weight:
416.64
UNSPSC Code:
12352211
NACRES:
NA.25
Assay
>99% (TLC)
form
powder
packaging
pkg of 1 × 1 mg (700127P-1mg)
pkg of 1 × 5 mg (700127P-5mg)
manufacturer/tradename
Avanti Research™ - A Croda Brand 700127P
shipped in
dry ice
storage temp.
−20°C
General description
7-keto-25-hydroxycholesterol synthesis from 7-ketocholesterol is catalyzed by the enzyme cholesterol 25-hydroxylase. 7β,25-dihydroxycholesterol (7β25OHC) is produced from the stereospecific reduction of 7k25OHC by the action of enzyme 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1). 11β-HSD type 2 enzyme catalyzes the reverse conversion of 7β25OHC to 7k25OHC.
Application
7-keto-25-hydroxycholesterol has been used as a substrate for 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) expressed in human embryonic kidney (HEK)-293 cells to test the oxoreduction functionality of the enzyme. It has also been used to test its effect on Epstein-Barr virus-induced seven-transmembrane receptor (EB12) activation.
Biochem/physiol Actions
7-keto-25-hydroxycholesterol (7k25OHC) might interact with the cysteine-rich domain (CRD) of the smoothened (Smo) in the hedgehog pathway. However, 7-keto-25-OHC is incapable of activating Smo.
Packaging
5 mL Amber Glass Screw Cap Vial (700127P-1mg)
5 mL Amber Glass Screw Cap Vial (700127P-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)
No data available
Flash Point(C)
No data available
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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Pengxiang Huang et al.
Cell, 166(5), 1176-1187 (2016-08-23)
In vertebrates, sterols are necessary for Hedgehog signaling, a pathway critical in embryogenesis and cancer. Sterols activate the membrane protein Smoothened by binding its extracellular, cysteine-rich domain (CRD). Major unanswered questions concern the nature of the endogenous, activating sterol and the
Benjamin R Myers et al.
Developmental cell, 26(4), 346-357 (2013-08-21)
Hedgehog (Hh) signaling during development and in postembryonic tissues requires activation of the 7TM oncoprotein Smoothened (Smo) by mechanisms that may involve endogenous lipidic modulators. Exogenous Smo ligands previously identified include the plant sterol cyclopamine (and its therapeutically useful synthetic
Katharina R Beck et al.
The Journal of steroid biochemistry and molecular biology, 190, 19-28 (2019-03-25)
Oxysterols are cholesterol metabolites derived through either autoxidation or enzymatic processes. They consist of a large family of bioactive lipids that have been associated with the progression of multiple pathologies. In order to unravel (patho-)physiological mechanisms involving oxysterols, it is
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