7α-Hydroxy-4-cholesten-3-one

Modify Date: 2024-01-02 18:24:58

7α-Hydroxy-4-cholesten-3-one Structure
7α-Hydroxy-4-cholesten-3-one structure
Common Name 7α-Hydroxy-4-cholesten-3-one
CAS Number 3862-25-7 Molecular Weight 400.63700
Density 1.03g/cm3 Boiling Point 516.7ºC at 760 mmHg
Molecular Formula C27H44O2 Melting Point 182-184ºC
MSDS N/A Flash Point 218.5ºC

 Use of 7α-Hydroxy-4-cholesten-3-one


7α-Hydroxy-4-cholesten-3-one is an intermediate in synthesis of bile acids from cholesterol. 7α-Hydroxy-4-cholesten-3-one is a pregnane X receptor (PXR) agonist. 7α-Hydroxy-cholest-4-en-3-one is a biomarker for bile acid loss, irritable bowel syndrome, and other diseases associated with defective bile acid biosynthesis. 7α-Hydroxy-cholest-4-en-3-one is the physiological substrate for CYP8B1[1][2].

 Names

Name 7α-hydroxycholest-4-en-3-one
Synonym More Synonyms

 7α-Hydroxy-4-cholesten-3-one Biological Activity

Description 7α-Hydroxy-4-cholesten-3-one is an intermediate in synthesis of bile acids from cholesterol. 7α-Hydroxy-4-cholesten-3-one is a pregnane X receptor (PXR) agonist. 7α-Hydroxy-cholest-4-en-3-one is a biomarker for bile acid loss, irritable bowel syndrome, and other diseases associated with defective bile acid biosynthesis. 7α-Hydroxy-cholest-4-en-3-one is the physiological substrate for CYP8B1[1][2].
Related Catalog
Target

Endogenous Metabolite[1] Pregnane X receptor (PXR)[1]

In Vitro 7α-Hydroxy-4-cholesten-3-one is found relatively upstream in the biosynthetic pathway to bile acids (e.g. chenodeoxycholic acid). The first step is the incorporation of the 7α-hydroxy group onto cholesterol by cytochrome P450 7A1, and the second step is the oxidation and isomerization of the 3-hydroxy group and the Δ5,6-double bond by 3β-hydroxy steroid dehydrogenase to yield 7α-Hydroxy-4-cholesten-3-one. The deletion of the gene that expresses P450 27A1, which is found downstream in the bile acid pathway, results in the accumulation of the precursor, 7α-Hydroxy-4-cholesten-3-one[1].
In Vivo 7α-Hydroxy-4-cholesten-3-one strongly relates to the hepatic enzymatic activity of CYP7A1 at steady-state conditions as well as during the rapid diurnal changes that occur in the rat. That serum 7α-Hydroxy-4-cholesten-3-one has a pronounced diurnal rhythm[2].
References

[1]. Offei SD, et al. Chemical synthesis of 7α-hydroxycholest-4-en-3-one, a biomarker for irritable bowel syndrome and bile acid malabsorption. Steroids. 2019 Nov;151:108449.

[2]. Gälman C, et al. Bile acid synthesis in humans has a rapid diurnal variation that is asynchronous with cholesterol synthesis. Gastroenterology. 2005 Nov;129(5):1445-53.

 Chemical & Physical Properties

Density 1.03g/cm3
Boiling Point 516.7ºC at 760 mmHg
Melting Point 182-184ºC
Molecular Formula C27H44O2
Molecular Weight 400.63700
Flash Point 218.5ºC
Exact Mass 400.33400
PSA 37.30000
LogP 6.56770
Index of Refraction 1.53
Storage condition -20°C

 Synthetic Route

 Synonyms

7alpha-Hydroxy-4-cholesten-3-one
Cholest-4-en-7alpha-ol-3-one
(7R,8S,9S,10R,13R,14S,17R)-7-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
7-Hydroxycholest-4-en-3-one
7|A-Hydroxy-4-cholesten-3-one
7alpha-Hydroxycholest-4-en-3-one
7alpha-hydroxycholest-4-en-3-one
7a-hydroxy-cholestene-3-one