Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

52853

Supelco

7α-Hydroxy-4-cholesten-3-one

≥95.0% (HPLC)

Synonym(s):

7α-Hydroxycholest-4-en-3-one

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C27H44O2
CAS Number:
3862-25-7
Molecular Weight:
400.64
MDL number:
MFCD00870345
UNSPSC Code:
41116107
PubChem Substance ID:
329757894
NACRES:
NA.24
Pricing and availability is not currently available.

grade

analytical standard

Quality Level

100

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.[1]

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)[2] as well as LC-MS.[1]
  • Rat and monkey plasma by LC-ESI-MS/MS working on multiple reaction monitoring (MRM) mode of detection.[3]
  • Peripheral blood plasma by solid-phase extraction (SPE) and HPLC.[4]

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
BCCL2141
BCCK3411
BCCJ7832
BCCJ7833
BCCG4643

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
Lijuan Kang et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 1064, 49-55 (2017-09-16)
7α-hydroxy-4-cholesten-3-one (C4) is an oxidative enzymatic product of cholesterol metabolism via cholesterol 7α-hydroxylase, an enzyme also known as cholesterol 7-alpha-monooxygenase or cytochrome P450 7A1 (CYP7A1). C4 is a stable intermediate in the rate limiting pathway of bile acid biosynthesis. Previous
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)
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)
Comparison of simple extraction procedures in liquid chromatography-mass spectrometry based determination of serum 7?-hydroxy-4-cholesten-3-one, a surrogate marker of bile acid synthesis.
Marek L, et al.
Journal of Chromatography. B, Biomedical Sciences and Applications, 1033, 317-320 (2016)
View All Related Papers

Questions

Reviews

No rating value

Active Filters

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