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:
Molecular Weight:
400.64
NACRES:
NA.24
PubChem Substance ID:
UNSPSC Code:
41116107
MDL number:
Pricing and availability is not currently available.
grade
analytical standard
Quality Segment
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.
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This Item | |||
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| format neat | format - | format - | format neat |
| grade analytical standard | grade - | grade - | grade analytical standard |
| application(s) clinical testing | application(s) - | application(s) - | application(s) clinical testing |
| storage temp. −20°C | storage temp. - | storage temp. - | storage temp. −20°C |
| Quality Level 100 | Quality Level 200 | Quality Level 200 | Quality Level 100 |
| assay ≥95.0% (HPLC) | assay - | assay ≥95% | assay ≥95.0% (HPLC) |
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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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)
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