3beta,5alpha,6beta-Trihydroxycholestane

Base Information

• Chemical Name: 3beta,5alpha,6beta-Trihydroxycholestane
• CAS No.: 1253-84-5
• Deprecated CAS: 72879-16-4,115510-05-9,2023759-81-9
• Molecular Formula: C27H48 O3
• Molecular Weight: 420.676
• NSC Number: 124751,18178
• UNII: 5XAB8PH90A
• DSSTox Substance ID: DTXSID70862612
• Nikkaji Number: J40.579E
• Wikidata: Q27103493
• Metabolomics Workbench ID: 34382
• ChEMBL ID: CHEMBL1278089
• Mol file: 1253-84-5.mol

Synonyms:5alpha-cholestane-3beta,5,6beta-triol;cholestane-3 beta,5 alpha,6 beta-triol;cholestane-3,5,6-triol;cholestane-3,5,6-triol, (3beta)-isomer;cholestane-3,5,6-triol, (3beta, 5alpha, 6alpha)-isomer;cholestane-3,5,6-triol, (3beta, 5alpha, 6beta)-isomer;cholestane-3,5,6-triol, (3beta, 5beta, 6beta)-isomer;cholestane-3,5,6-triol, (3beta, 6beta)-isomer

Chemical Property of 3beta,5alpha,6beta-Trihydroxycholestane

Chemical Property:

• Vapor Pressure: 8.58E-13mmHg at 25°C
• Melting Point: 226-231°C
• Boiling Point: 515.7°Cat760mmHg
• PKA: 14.26±0.70(Predicted)
• Flash Point: 212.5°C
• PSA: 60.69000
• Density: 1.065g/cm³
• LogP: 5.55430
• Storage Temp.: Refrigerator
• Solubility.: Methanol (Slightly)
• XLogP3: 7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 420.36034539
• Heavy Atom Count: 30
• Complexity: 619

Purity/Quality:

99% ^*data from raw suppliers

3β,5α,6β-Trihydroxycholestane ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 20/21/22-68/20/21/22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)CCCC(C)C1CCC2C1(CCC3C2CC(C4(C3(CCC(C4)O)C)O)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]([C@@]4([C@@]3(CC[C@@H](C4)O)C)O)O)C
• Uses: Cholesterol analog. Useful for treatment of hyperlipemia, arteriosclerosis, diabetes, obesity. Cholesterol analog. Cholestane-3β,5α,6β-Triol is useful for treatment of hyperlipemia, arteriosclerosis, diabetes, obesity.

Technology Process of 3beta,5alpha,6beta-Trihydroxycholestane

There total 45 articles about 3beta,5alpha,6beta-Trihydroxycholestane 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: 93.0%

cholesterol (57-88-5) → cholestanetriol (1253-84-5)

Guidance literature:

cholesterol; With monoperoxyphthalic acid magnesium salt hexahydrate; In acetone; at 57 ℃; for 0.5h;

With bismuth(lll) trifluoromethanesulfonate; In acetone; at 20 ℃; for 0.5h;

DOI:10.1021/jm1007769

Reference yield: 92.0%

(6aS,6bS,9R,9aR,11aS,11bR)-9a,11b-dimethyl-9-((R)-6-methylheptan-2-yl)hexadecahydrocyclopenta[1,2]phenanthro[8a,9-b]oxiren-3-ol (55700-78-2) → cholestanetriol (1253-84-5)

Guidance literature:

With tris(trifluoroacetato)bismuth(III); water; In acetone; at 20 ℃; for 0.5h;

DOI:10.1016/j.tet.2010.01.089

Reference yield: 85.0%

3β-acetoxycholestane-5α,6β-diol (2701-08-8,35089-26-0,98076-44-9,117465-73-3,123285-93-8,1857-99-4) → cholestanetriol (1253-84-5)

Guidance literature:

With methanol; sodium methylate; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/j.bmcl.2014.05.064

upstream raw materials:

cholesterol

Cholesteryl acetate

epicholesterol

cholesterol

Downstream raw materials:

3β,5-dihydroxy-5α-cholestan-6-one

5α-cholestane-5-ol-3,6-dione

5β-methyl-19-norcholest-9(10)-ene-3β,6β-diol 3,6-diacetate

benzoic acid-(5,6β-dihydroxy-5α-cholestan-3β-yl ester)

Refernces

Some Reactions of α- and β-Cholesteryl Benzoate Oxides

10.1039/jr9390001356

The study investigates the reactions of α- and β-cholesteryl benzoate oxides, which are prepared through the treatment of cholesteryl benzoate with perbenzoic acid. These oxides are key compounds in the research. α-Cholesteryl benzoate oxide, when treated with hydrochloric acid, yields 6-chloro-5-hydroxy-3-benzoyloxycholestane, which upon dehydration forms 6-chloro-3-benzoyloxy-A4-cholestene. Similarly, β-cholesteryl benzoate oxide reacts with hydrochloric acid to produce 5-chloro-6-hydroxy-3-benzoyloxycholestane. The study also explores the isomerization of α-cholesteryl benzoate oxide to 6-ketocholestanyl benzoate using dehydrated alum or phosphoric oxide. Additionally, the researchers attempted to replicate the preparation of α-benzoate oxide via pyrolysis of the dibenzoate of 3:5:6-trihydroxycholestane, but encountered issues with impurities. The study provides detailed experimental procedures and characterizations of the compounds involved, highlighting the differences in behavior between α- and β-cholesteryl benzoate oxides and their derivatives.