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700113P

Avanti

7α-hydroxycholestenone

7α-hydroxy-4-cholesten-3-one, powder

Synonym(s):
C4; α-HC; α-HC; 7HCO; 7 α-3ox-C; 111107
Empirical Formula (Hill Notation):
C27H44O2
CAS Number:
Molecular Weight:
400.64
NACRES:
NA.25

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 700113P

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]

Packaging

5 mL Amber Glass Screw Cap Vial (700113P-10mg)
5 mL Amber Glass Screw Cap Vial (700113P-1mg)

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

The enzymes, regulation, and genetics of bile acid synthesis. Annual review of biochemistry
Russell DW
Annual Review of Biochemistry, 72, 137-174 (2003)
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)
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)
Cecilia Gälman et al.
Gastroenterology, 129(5), 1445-1453 (2005-11-16)
The conversion of cholesterol to bile acids by the liver is an important regulator of body cholesterol homeostasis. In rodents, both cholesterol and bile acid synthesis have marked diurnal rhythms that peak synchronously at midnight. The aim of this study

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