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Merck
CN

52853

7α-Hydroxy-4-cholesten-3-one

≥95.0% (HPLC)

Synonym(s):

7α-Hydroxycholest-4-en-3-one

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About This Item

Empirical Formula (Hill Notation):
C27H44O2
CAS Number:
3862-25-7
Molecular Weight:
400.64
NACRES:
NA.24
PubChem Substance ID:
329757894
UNSPSC Code:
41116107
MDL number:
MFCD00870345

Key Documents

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InChI key

IOIZWEJGGCZDOL-RQDYSCIWSA-N

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

grade

analytical standard

assay

≥95.0% (HPLC)

application(s)

clinical testing

format

neat

storage temp.

−20°C

Quality Level

100

Related Categories

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN7046
BCCL2141
BCCK3411
BCCJ7832
BCCJ7833

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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
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
A UHPLC-MS/MS method for the quantification of 7?-hydroxy-4-cholesten-3-one to assist in diagnosis of bile acid malabsorption.
Prost JC, et al.
Clinical mass spectrometry, 3, 1-6 (2017)
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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