Introduction：Basic information about CAS 3862-25-7|7α-Hydroxy-4-cholesten-3-one, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | 7α-Hydroxy-4-cholesten-3-one |
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| CAS Number | 3862-25-7 | Molecular Weight | 400.63700 |
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| Density | 1.03g/cm3 | Boiling Point | 516.7ºC at 760 mmHg |
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| Molecular Formula | C27H44O2 | Melting Point | 182-184ºC |
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| MSDS | / | Flash Point | 218.5ºC |
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Names
| Name | 7α-hydroxycholest-4-en-3-one |
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| Synonym | More Synonyms |
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7α-Hydroxy-4-cholesten-3-one BiologicalActivity
| 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]. |
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| Related Catalog | Research Areas >>Metabolic Disease |
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| Target | Endogenous Metabolite[1] Pregnane X receptor (PXR)[1] |
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| 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]. |
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| 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]. |
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| 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. |
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Chemical & Physical Properties
| Density | 1.03g/cm3 |
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| Boiling Point | 516.7ºC at 760 mmHg |
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| Melting Point | 182-184ºC |
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| Molecular Formula | C27H44O2 |
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| Molecular Weight | 400.63700 |
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| Flash Point | 218.5ºC |
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| Exact Mass | 400.33400 |
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| PSA | 37.30000 |
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| LogP | 6.56770 |
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| Index of Refraction | 1.53 |
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| InChIKey | IOIZWEJGGCZDOL-RQDYSCIWSA-N |
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| SMILES | CC(C)CCCC(C)C1CCC2C3C(O)CC4=CC(=O)CCC4(C)C3CCC12C |
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| Storage condition | -20°C |
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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 |
