7alpha-Hydroxy-4-cholesten-3-one

Base Information

• Chemical Name: 7alpha-Hydroxy-4-cholesten-3-one
• CAS No.: 3862-25-7
• Molecular Formula: C27H44O2
• Molecular Weight: 400.645
• DSSTox Substance ID: DTXSID10191938
• Nikkaji Number: J602.383E
• Wikipedia: 7%CE%B1-Hydroxy-4-cholesten-3-one
• Wikidata: Q4644247
• Metabolomics Workbench ID: 36794
• ChEMBL ID: CHEMBL4285345
• Mol file: 3862-25-7.mol

Synonyms:7 alpha-hydroxy-4-cholesten-3-one;7-hydroxy-4-cholesten-3-one;7alpha-hydroxy-4-cholesten-3-one;cholest-4-en-7 alpha-ol-3-one

Chemical Property of 7alpha-Hydroxy-4-cholesten-3-one

Chemical Property:

• Appearance/Colour: White Solid
• Vapor Pressure: 7.76E-13mmHg at 25°C
• Melting Point: 182-184 °C
• Refractive Index: 1.53
• Boiling Point: 516.7 °C at 760 mmHg
• PKA: 14.49±0.70(Predicted)
• Flash Point: 218.5 °C
• PSA: 37.30000
• Density: 1.03 g/cm³
• LogP: 6.56770
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 7.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 400.334130642
• Heavy Atom Count: 29
• Complexity: 663

Purity/Quality:

99%, ^*data from raw suppliers

7α-Hydroxy-4-cholesten-3-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CCCC(C)C1CCC2C1(CCC3C2C(CC4=CC(=O)CCC34C)O)C
• Isomeric SMILES: C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2[C@@H](CC4=CC(=O)CC[C@]34C)O)C
• Description: 7α-hydroxy-4-Cholesten-3-one is a metabolite of 7α-hydroxy cholesterol and an intermediate in the biosynthesis of bile acids. Plasma levels of 7α-hydroxy-4-cholesten-3-one positively correlate with the rate of bile acid synthesis in humans and are increased in patients following ileal resection.
• Uses: 7α-Hydroxy-4-cholesten-3-one is a metabolite of Cholesterol (C432501).

Technology Process of 7alpha-Hydroxy-4-cholesten-3-one

There total 15 articles about 7alpha-Hydroxy-4-cholesten-3-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 69.0%

7α-formyloxy-4-cholesten-3-one (1448262-85-8) → cholesta-4,6-dien-3-one (566-93-8) + Δ4-7α-hydrocholesterol (3862-25-7)

Guidance literature:

With potassium carbonate; In methanol; for 12h; Reagent/catalyst; Solvent;

DOI:10.1016/j.steroids.2019.108449

Reference yield:

7-ketocholesteryl acetate (809-51-8) → cholesta-4,6-dien-3-one (566-93-8) + Δ4-7α-hydrocholesterol (3862-25-7)

Guidance literature:

Multi-step reaction with 10 steps

1: L-Selectride / tetrahydrofuran / 3 h / -78 °C / Inert atmosphere; Sealed tube

2: 1H-imidazole / acetonitrile / 4 h / Reflux

3: potassium carbonate / methanol / 4 h / Reflux

4: aluminum isopropoxide; 1-Methyl-4-piperidone / toluene / 24 h / Dean-Stark; Reflux; Darkness

5: trifluoroacetic acid; acetic acid; sodium tetrahydroborate / acetonitrile; dichloromethane / 2 h / 0 °C

6: toluene-4-sulfonic acid / dichloromethane; methanol / 2 h / Reflux

7: toluene-4-sulfonic acid / 2 h / Reflux

8: tetrakis(μ-caprolactamato)dirhodium(Rh-Rh); tert.-butylhydroperoxide / 1,2-dichloro-ethane / 17 h

9: Dess-Martin periodane

10: potassium carbonate / methanol / 12 h

With 1H-imidazole; 1-Methyl-4-piperidone; tert.-butylhydroperoxide; sodium tetrahydroborate; tetrakis(μ-caprolactamato)dirhodium(Rh-Rh); aluminum isopropoxide; L-Selectride; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane; toluene; acetonitrile; 4: |Oppenauer Oxidation;

DOI:10.1016/j.steroids.2019.108449

Reference yield:

7α-hydroxycholest-5-en-3β-yl 3-acetate (19317-90-9) → cholesta-4,6-dien-3-one (566-93-8) + Δ4-7α-hydrocholesterol (3862-25-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 1H-imidazole / acetonitrile / 4 h / Reflux

2: potassium carbonate / methanol / 4 h / Reflux

3: aluminum isopropoxide; 1-Methyl-4-piperidone / toluene / 24 h / Dean-Stark; Reflux; Darkness

4: trifluoroacetic acid; acetic acid; sodium tetrahydroborate / acetonitrile; dichloromethane / 2 h / 0 °C

5: toluene-4-sulfonic acid / dichloromethane; methanol / 2 h / Reflux

6: toluene-4-sulfonic acid / 2 h / Reflux

7: tetrakis(μ-caprolactamato)dirhodium(Rh-Rh); tert.-butylhydroperoxide / 1,2-dichloro-ethane / 17 h

8: potassium carbonate / methanol / 12 h

With 1H-imidazole; 1-Methyl-4-piperidone; tert.-butylhydroperoxide; sodium tetrahydroborate; tetrakis(μ-caprolactamato)dirhodium(Rh-Rh); aluminum isopropoxide; potassium carbonate; toluene-4-sulfonic acid; acetic acid; trifluoroacetic acid; In methanol; dichloromethane; 1,2-dichloro-ethane; toluene; acetonitrile; 3: |Oppenauer Oxidation;

DOI:10.1016/j.steroids.2019.108449

upstream raw materials:

7-ketocholesteryl acetate

7α-hydroxycholest-5-en-3β-yl 3-acetate

cholest-4-en-7α-ol

7α-formyloxy-4-cholesten-3-one

Downstream raw materials:

7α,12α-dihydroxy-4-cholesten-3-one

Refernces

• 1、 Griffiths, William J.,Gilmore, Ian,Yutuc, Eylan,Abdel-Khalik, Jonas,Crick, Peter J.,Hearn, Thomas,Dickson, Alison,Bigger, Brian W.,Wu, Teresa Hoi-Yee,Goenka, Anu,Ghosh, Arunabha,Jones, Simon A.,Wang, Yuqin. "Identification of unusual oxysterols and bile acids with 7-oxo or 3,5,6-trihydroxy functions in human plasma by charge-tagging mass spectrometry with multistage fragmentation". . p. 1058 - 1070. Retrieved 2018/06/11.