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7α-Hydroxy-4-cholesten-3-one

Names

[ CAS No. ]:
3862-25-7

[ Name ]:
7α-Hydroxy-4-cholesten-3-one

[Synonym ]:
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

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]:

Research Areas >> Metabolic Disease

[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

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds