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Merck

52853

Supelco

7α-Hydroxy-4-cholesten-3-one

≥95.0% (HPLC)

Sinónimos:

7α-Hydroxycholest-4-en-3-one

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About This Item

Fórmula empírica (notación de Hill):
C27H44O2
Número de CAS:
Peso molecular:
400.64
MDL number:
UNSPSC Code:
41116107
PubChem Substance ID:
NACRES:
NA.24

grade

analytical standard

Quality Level

assay

≥95.0% (HPLC)

application(s)

clinical testing

format

neat

storage temp.

−20°C

SMILES string

O=C1CC[C@@]2(C)C(C[C@@H](O)[C@]3([H])[C@]2([H])CC[C@@]4(C)[C@@]3([H])CC[C@]4([H])[C@H](C)CCCC(C)C)=C1

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 (C4) is known as a marker for the cholesterol 7α-hydroxylase activity. It plays an important role in bile acid metabolism.

Application

C4 may be used as a reference standard for the determination of C4 in:
  • Human serum by ultra-high performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS) with electrospray ionization source (ESI) as well as LC-MS.
  • Rat and monkey plasma by LC-ESI-MS/MS working on multiple reaction monitoring (MRM) mode of detection.
  • Peripheral blood plasma by solid-phase extraction (SPE) and HPLC.

Biochem/physiol Actions

7a-Hydroxycholestene-3-one, a metabolite in bile acid synthesis, is derived from 7a-hydroxycholesterol and can be further metabolized to 7a,12a,-dihydroxycholest-4-en-3-one. Analysis of 7a-Hydroxycholestene-3-one (HCO) in serum may serve as a novel, simple, and sensitive method for the detection of bile acid malabsorption in patients with chronic diarrhea of unknown origin.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Marcos Pedrosa et al.
Contemporary clinical trials, 88, 105889-105889 (2019-11-16)
Nonalcoholic steatohepatitis (NASH) is a multifactorial disease involving different contributing mechanisms, with no approved therapies so far. Tropifexor (TXR), a farnesoid X receptor agonist, and cenicriviroc (CVC), a chemokine receptor types 2/5 antagonist, target the steatotic, inflammatory, and/or fibrotic pathways
LC-MS/MS quantification of 7?-hydroxy-4-cholesten-3-one (C4) in rat and monkey plasma.
Kang L, et al.
Journal of Chromatography. B, Biomedical Sciences and Applications, 1064, 49-55 (2017)
C G Hillebrant et al.
European journal of clinical investigation, 28(4), 324-328 (1998-06-06)
HMG-CoA reductase inhibitors are now the therapy of choice in the treatment of hypercholesterolaemia. The effects of long-term treatment with these substances on plasma lipoproteins, cholesterol metabolism and biliary secretion of lipids have been extensively studied in humans. Much less
Monitoring hepatic cholesterol 7?-hydroxylase activity by assay of the stable bile acid intermediate 7?-hydroxy-4-cholesten-3-one in peripheral blood.
Galman C, et al.
Journal of Lipid Research, 44(4), 859-866 (2003)
Michael K Badman et al.
Clinical pharmacology in drug development, 9(3), 395-410 (2019-12-12)
Tropifexor (LJN452) is a potent, orally available, non-bile acid farnesoid X receptor agonist under clinical development for chronic liver diseases. Here, we present results from a first-in-human study of tropifexor following single- and multiple-ascending doses (SAD/MAD) and food effect substudy

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