7alpha,12alpha-Dihydroxycholest-4-en-3-one

Base Information

• Chemical Name: 7alpha,12alpha-Dihydroxycholest-4-en-3-one
• CAS No.: 1254-03-1
• Molecular Formula: C₂₇H₄₄O₃
• Molecular Weight: 416.645
• DSSTox Substance ID: DTXSID80925121
• Nikkaji Number: J1.513.288D
• Wikidata: Q27103727
• Metabolomics Workbench ID: 36786
• Mol file: 1254-03-1.mol

Synonyms:7 alpha,12 alpha-dihydroxy-5-cholesten-3-one

Chemical Property of 7alpha,12alpha-Dihydroxycholest-4-en-3-one

Chemical Property:

• Vapor Pressure: 2.2E-14mmHg at 25°C
• Melting Point: 215-218?C
• Refractive Index: 1.542
• Boiling Point: 549.9 °C at 760 mmHg
• Flash Point: 300.4 °C
• PSA: 57.53000
• Density: 1.07 g/cm³
• LogP: 5.53850
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 416.32904526
• Heavy Atom Count: 30
• Complexity: 696

Purity/Quality:

98%Min ^*data from raw suppliers

7α,12α-Dihydroxycholest-4-en-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(C(CC3C2C(CC4=CC(=O)CCC34C)O)O)C
• Isomeric SMILES: C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2[C@@H](CC4=CC(=O)CC[C@]34C)O)O)C
• Uses: A metabolite of Hydroxycholesterol and Hydroxysitosterol.

Technology Process of 7alpha,12alpha-Dihydroxycholest-4-en-3-one

There total 15 articles about 7alpha,12alpha-Dihydroxycholest-4-en-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: 80.0%

7α,12α-diformyloxy-4-cholesten-3-one (1448262-82-5) → 7α,12α-dihydroxy-4-cholesten-3-one (1254-03-1)

Guidance literature:

With water; sodium hydroxide; for 0.5h;

DOI:10.1016/j.steroids.2013.05.011

Reference yield:

cholic acid (81-25-4) → 7α,12α-dihydroxy-4-cholesten-3-one (1254-03-1)

Guidance literature:

Multi-step reaction with 11 steps

1.1: dmap / pyridine / 1 h / 40 °C

2.1: triethylamine; chloroformic acid ethyl ester / tetrahydrofuran / 2 h / 20 °C

2.2: 2 h / 0 °C

3.1: potassium bromide; sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane / 0 °C

4.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / 0 °C

4.2: 0.25 h / 0 °C

5.1: hydrogen; palladium 10% on activated carbon / methanol; ethyl acetate; acetic acid / 3 h / 20 °C

6.1: hydrogenchloride / methanol; water / 6 h / 30 °C

7.1: Jones reagent / acetone; dichloromethane / 0.5 h / 0 °C

8.1: potassium hydroxide; water / methanol / 16 h / 30 °C

9.1: perchloric acid / water / 1 h / 20 °C

10.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; trifluoroacetic acid / dimethyl sulfoxide / 40 h / 40 °C

11.1: water; sodium hydroxide / 0.5 h

With hydrogenchloride; dmap; sodium hypochlorite; Jones reagent; n-butyllithium; perchloric acid; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; palladium 10% on activated carbon; water; hydrogen; chloroformic acid ethyl ester; triethylamine; trifluoroacetic acid; potassium bromide; potassium hydroxide; sodium hydroxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; water; acetic acid; dimethyl sulfoxide; ethyl acetate; acetone; 4.2: |Wittig Olefination;

DOI:10.1016/j.steroids.2013.05.011

Reference yield:

cholic acid 3,7,12-triacetate (52840-09-2) → 7α,12α-dihydroxy-4-cholesten-3-one (1254-03-1)

Guidance literature:

Multi-step reaction with 10 steps

1.1: triethylamine; chloroformic acid ethyl ester / tetrahydrofuran / 2 h / 20 °C

1.2: 2 h / 0 °C

2.1: potassium bromide; sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane / 0 °C

3.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / 0 °C

3.2: 0.25 h / 0 °C

4.1: hydrogen; palladium 10% on activated carbon / methanol; ethyl acetate; acetic acid / 3 h / 20 °C

5.1: hydrogenchloride / methanol; water / 6 h / 30 °C

6.1: Jones reagent / acetone; dichloromethane / 0.5 h / 0 °C

7.1: potassium hydroxide; water / methanol / 16 h / 30 °C

8.1: perchloric acid / water / 1 h / 20 °C

9.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; trifluoroacetic acid / dimethyl sulfoxide / 40 h / 40 °C

10.1: water; sodium hydroxide / 0.5 h

With hydrogenchloride; sodium hypochlorite; Jones reagent; n-butyllithium; perchloric acid; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; palladium 10% on activated carbon; water; hydrogen; chloroformic acid ethyl ester; triethylamine; trifluoroacetic acid; potassium bromide; potassium hydroxide; sodium hydroxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; hexane; dichloromethane; water; acetic acid; dimethyl sulfoxide; ethyl acetate; acetone; 3.2: |Wittig Olefination;

DOI:10.1016/j.steroids.2013.05.011

upstream raw materials:

cholic acid

cholic acid 3,7,12-triacetate

3α,7α,12α-triacetoxy-5β-cholane-24-ol

(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-10,13-dimethyl-17-((R)-5-oxopentan-2-yl)hexadecahydro-1H-cyclopenta[a] phenanthrene-3,7,12-triyl triacetate

Refernces

• 1、 Griffiths, William J.,Crick, Peter J.,Meljon, Anna,Theofilopoulos, Spyridon,Abdel-Khalik, Jonas,Yutuc, Eylan,Parker, Josie E.,Kelly, Diane E.,Kelly, Steven L.,Arenas, Ernest,Wang, Yuqin. "Additional pathways of sterol metabolism: Evidence from analysis of Cyp27a1?/? mouse brain and plasma". . p. 191 - 211. Retrieved 2019/01/03.