700112P
Avanti
7α-hydroxycholestenone-d7
7α-hydroxy-4-cholesten-3-one-d7, powder
Synonym(s):
25,26,26,26,27,27,27-heptadeutero-7α-hydroxy-4-cholesten-3-one ; 111106
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About This Item
Empirical Formula (Hill Notation):
C27H37D7O2
CAS Number:
Molecular Weight:
407.68
UNSPSC Code:
41141804
NACRES:
NA.25
Recommended Products
Assay
>99% (TLC)
form
powder
packaging
pkg of 1 × 1 mg (700112P-1mg)
pkg of 1 × 10 mg (700112P-10mg)
pkg of 1 × 5 mg (700112P-5mg)
manufacturer/tradename
Avanti Research™ - A Croda Brand 700112P
shipped in
dry ice
storage temp.
−20°C
General description
7α-Hydroxy-4-cholesten-3-one is an intermediate in the biochemical synthesis of bile acids from cholesterol.
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]
Biochem/physiol Actions
7α-Hydroxy-4-cholesten-3-one 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. Elevated values of 7α-hydroxy-4-cholesten-3-one are found in patients with bile acid malabsorption. It a may be useful in the diagnosis of this condition as high values are associated with low 75-selenium homocholic acid taurine (SeHCAT) retention. The levels of 7α-hydroxy-4-cholesten-3-one is elevated in irritable bowel syndrome with diarrhea (IBS-D). Deuterium labeled 7α-hydroxy-4-cholesten-3-one (d7-7αC4) is employed as an internal standard in the liquid chromatography-tandem mass spectrometry (LC-MS/MS) measurements.
Packaging
5 mL Amber Glass Screw Cap Vial (700112P-10mg)
5 mL Amber Glass Screw Cap Vial (700112P-1mg)
5 mL Amber Glass Screw Cap Vial (700112P-5mg)
Legal Information
Avanti Research is a trademark of Avanti Polar Lipids, LLC
Storage Class Code
11 - Combustible Solids
Flash Point(F)
No data available
Flash Point(C)
No data available
Certificates of Analysis (COA)
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M Camilleri et al.
Neurogastroenterology and motility : the official journal of the European Gastrointestinal Motility Society, 21(7), 734-e43-734-e43 (2009-04-17)
Bile acid malabsorption (BAM) is reported in up to 50% of patients with functional diarrhoea and irritable bowel syndrome with diarrhoea (IBS-D). Serum 7alpha-hydroxy-4-cholesten-3-one (7alphaHCO or 7alphaC4), an indirect measurement of hepatic bile acid synthesis, has been validated as a
W Gordon Brydon et al.
Canadian journal of gastroenterology = Journal canadien de gastroenterologie, 25(6), 319-323 (2011-07-19)
Bile acid malabsorption (BAM) is a recognized cause of watery diarrhea, often diagnosed empirically based on clinical response to cholestyramine. The radionuclide selenium-labelled homocholic acid-taurine whole body retention test is expensive, labour intensive and of limited availability. To report on
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)
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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