4-Cholesten-6beta-ol-3-one

Base Information

• Chemical Name: 4-Cholesten-6beta-ol-3-one
• CAS No.: 570-89-8
• Molecular Formula: C27H44 O2
• Molecular Weight: 400.645
• DSSTox Substance ID: DTXSID40972494
• Nikkaji Number: J482.368K
• Wikidata: Q82956268
• ChEMBL ID: CHEMBL302348
• Mol file: 570-89-8.mol

Synonyms:4-cholesten-6-ol-3-one;4-cholesten-6beta-ol-3-one

Chemical Property of 4-Cholesten-6beta-ol-3-one

Chemical Property:

• Vapor Pressure: 6.75E-13mmHg at 25°C
• Boiling Point: 518°Cat760mmHg
• Flash Point: 219°C
• PSA: 37.30000
• Density: 1.03g/cm³
• LogP: 6.56770
• XLogP3: 7.2
• 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%min ^*data from raw suppliers

4-CHOLESTEN-6BETA-OL-3-ONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CCCC(C)C1CCC2C1(CCC3C2CC(C4=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]2C[C@H](C4=CC(=O)CC[C@]34C)O)C

Technology Process of 4-Cholesten-6beta-ol-3-one

There total 14 articles about 4-Cholesten-6beta-ol-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: 13.0%

cholesterol (57-88-5) → Cholest-4-en-3-one (601-57-0) + 4-cholestene-3,6-dione (54339-68-3,984-84-9) + cholest-4-ene-6β-hydroperoxy-3-one (2207-76-3) + 6β-hydroxycholest-4-en-3-one (570-89-8)

Guidance literature:

With E₃₆₁Q cholesterol oxidase; In isopropyl alcohol; at 37 ℃; for 24h; Further byproducts given;

DOI:10.1021/ja962258o

Reference yield: 13.0%

Cholest-5-en-3-one (601-54-7) → Cholest-4-en-3-one (601-57-0) + 4-cholestene-3,6-dione (54339-68-3,984-84-9) + cholest-4-ene-6β-hydroperoxy-3-one (2207-76-3) + 6β-hydroxycholest-4-en-3-one (570-89-8)

Guidance literature:

With E₃₆₁Q cholesterol oxidase; In isopropyl alcohol; at 37 ℃; for 24h; Further byproducts given;

DOI:10.1021/ja962258o

Reference yield: 13.0%

Cholest-5-en-3-one (601-54-7) → Cholest-4-en-3-one (601-57-0) + 4-cholestene-3,6-dione (54339-68-3,984-84-9) + cholest-4-ene-6β-hydroperoxy-3-one (2207-76-3) + 6β-hydroxycholest-4-en-3-one (570-89-8) + 6α-hydroxy-cholest-4-en-3-one (570-90-1) + cholest-4-ene-6α-hydroperoxy-3-one

Guidance literature:

With E₃₆₁Q cholesterol oxidase; In isopropyl alcohol; at 37 ℃; for 24h; Product distribution; transformations of cholesterol and cholest-5-ene-3-one catalyzed by wild-type or E₃₆₁Q cholesterol oxidase, enzyme activity, oxidation and stabilities of products, proposed mechanism;

DOI:10.1021/ja962258o

upstream raw materials:

Δ⁵-cholesten-3-one

6β-Hydroperoxycholest-4-en-3-one

cholesterol

Cholest-5-en-3-one

Downstream raw materials:

Cholest-4-en-3-one

5α-cholestane-3,6-dione

Benzoic acid (6R,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-6-yl ester

Refernces

• 1、 Sampson, Nicole S.,Kass, Ignatius J.. "Isomerization, but not oxidation, is suppressed by a single point mutation, E361Q, in the reaction catalyzed by cholesterol oxidase". . p. 855 - 862. Retrieved 2007/10/03.
• 2、 Dang, Hai-Shan,Davies, Alwyn G.,Schiesser, Carl H.. "Allylic Hydroperoxides Formed by Singlet Oxygenation of Cholest-5-en-3-one". . p. 789 - 794. Retrieved 2007/10/02.