700113P
Avanti
7α-hydroxycholestenone
Avanti Polar Lipids
Sign Into View Organizational & Contract Pricing
All Photos(1)
Synonym(s):
C4; α-HC; α-HC; 7HCO; 7 α-3ox-C; 111107
Empirical Formula (Hill Notation):
C27H44O2
Recommended Products
description
7α-hydroxy-4-cholesten-3-one
Assay
>99% (TLC)
form
powder
packaging
pkg of 1 × 1 mg (700113P-1mg)
pkg of 1 × 10 mg (700113P-10mg)
manufacturer/tradename
Avanti Polar Lipids
shipped in
dry ice
storage temp.
−20°C
InChI
1S/C27H44O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h15,17-18,21-25,29H,6-14,16H2,1-5H3/t18-,21-,22+,23+,24-,25+,26+,27-/m1/s1
InChI key
IOIZWEJGGCZDOL-RQDYSCIWSA-N
General description
7α-Hydroxy-4-cholesten-3-one is an intermediate in the biochemical synthesis of bile acids from cholesterol. Its precursor, 7α-hydroxycholesterol, is produced from cholesterol by hepatic cholesterol 7α-hydroxylase (CYP7A1).[1]It is metabolized by the enzyme 7α-hydroxycholest-4-en-3-one 12α-hydroxylase to 7α,12α-dihydroxycholest-4-en-3-one and then to cholic acid, the major primary bile acid in humans. Alternatively, it can be converted into 5β-cholestane-3α,7α-diol and then to chenodeoxycholic acid, the other major primary bile acid in humans.Serum 7α-hydroxy-4-cholesten-3-one concentrations reflect the activity of the bile acid synthetic pathway. Serum 7α-hydroxy-4-cholesten-3-one values vary during the day as bile acid synthetic rates have a diurnal rhythm.[2]Elevated values are found in patients with bile acid malabsorption and may be useful in the diagnosis of this condition as high values are associated with low SeHCAT retention.[3] The increase in serum 7α-hydroxy-4-cholesten-3-one concentrations reflects the loss of bile acids secondary to bile acid malabsorption or the increased synthesis found in primary bile acid diarrhea associated with impaired negative feedback of CYP7A1 by FGF19.[4]
Application
- Role as a mediator in cholesterol metabolism: 7α-hydroxycholestenone has been implicated in the discussion on oxysterols as cholesterol metabolites that act as significant mediators within biological systems, highlighting its importance in cholesterol metabolism and potential pharmaceutical implications (Mutemberezi et al., 2016).
Packaging
5 mL Amber Glass Screw Cap Vial (700113P-10mg)
5 mL Amber Glass Screw Cap Vial (700113P-1mg)
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’.
Already Own This Product?
Find documentation for the products that you have recently purchased in the Document Library.
The enzymes, regulation, and genetics of bile acid synthesis. Annual review of biochemistry
Russell DW
Annual Review of Biochemistry, 72, 137-174 (2003)
Bile acid synthesis in humans has a rapid diurnal variation that is asynchronous with cholesterol synthesis.
Galman C, et al.
Gastroenterology, 129(5), 1445-1453 (2005)
Chronic diarrhea due to excessive bile acid synthesis and not defective ileal transport: a new syndrome of defective fibroblast growth factor 19 release.
Hofmann AF, et al.
Clinical Gastroenterology and Hepatology : the Official Clinical Practice Journal of the American Gastroenterological Association, 7 (11), 1151-1154 (2009)
Serum 7 alpha-hydroxy-4-cholesten-3-one and selenohomocholyltaurine (SeHCAT) whole body retention in the assessment of bile acid induced diarrhoea.
Brydon WG, et al.
European Journal of Gastroenterology & Hepatology, 8(2), 117-123 (1996)
Chronic diarrhea due to excessive bile acid synthesis and not defective ileal transport: a new syndrome of defective fibroblast growth factor 19 release.
Alan F Hofmann et al.
Clinical gastroenterology and hepatology : the official clinical practice journal of the American Gastroenterological Association, 7(11), 1151-1154 (2009-08-12)
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