Stigmastane-3beta,5alpha,6beta-triol

Base Information

• Chemical Name: Stigmastane-3beta,5alpha,6beta-triol
• CAS No.: 20835-91-0
• Molecular Formula: C29H52O3
• Molecular Weight: 448.7214
• UNII: 83PAZ7H88D
• DSSTox Substance ID: DTXSID10943075
• Nikkaji Number: J591.487F
• Wikidata: Q27136062
• Metabolomics Workbench ID: 123196
• ChEMBL ID: CHEMBL1278178
• Mol file: 20835-91-0.mol

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

Chemical Property of Stigmastane-3beta,5alpha,6beta-triol

Chemical Property:

• Vapor Pressure: 1.05E-13mmHg at 25°C
• Boiling Point: 535.6°Cat760mmHg
• Flash Point: 216.1°C
• PSA: 60.69000
• Density: 1.047g/cm³
• LogP: 6.19040
• XLogP3: 7.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 448.39164552
• Heavy Atom Count: 32
• Complexity: 663

Purity/Quality:

98%min ^*data from raw suppliers

Stigmastane-3,5,6-triol,(3β,5α,6β)- 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(CCC(C)C1CCC2C1(CCC3C2CC(C4(C3(CCC(C4)O)C)O)O)C)C(C)C
• Isomeric SMILES: CC[C@H](CC[C@@H](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)C(C)C

Technology Process of Stigmastane-3beta,5alpha,6beta-triol

There total 8 articles about Stigmastane-3beta,5alpha,6beta-triol 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: 49.0%

β-sitosterol (83-46-5) → 3,5,6-trihydroxysitostane (16137-56-7,73544-41-9,133697-68-4,141610-97-1,20835-91-0)

Guidance literature:

β-sitosterol; With formic acid; at 80 ℃; for 0.166667h;

With dihydrogen peroxide; at 25 ℃; for 16h;

With sodium hydroxide; In methanol; at 20 ℃; for 3h;

DOI:10.1039/b505069c

Reference yield:

5α,6α- and 5β,6β-Epoxystigmastan-3β-ol (87303-93-3) → 3,5,6-trihydroxysitostane (16137-56-7,73544-41-9,133697-68-4,141610-97-1,20835-91-0)

Guidance literature:

With tris(trifluoroacetato)bismuth(III); water; In acetone; at 20 ℃; for 1h;

DOI:10.1016/j.tet.2010.01.089

Reference yield:

22,23-dihydro-i-stigmasterol methyl ether (108646-29-3) → 3,5,6-trihydroxysitostane (16137-56-7,73544-41-9,133697-68-4,141610-97-1,20835-91-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: aq. TsOH / dioxane / 3 h / 80 °C

2.1: aq. HCOOH / 0.17 h / 80 °C

2.2: aq. H₂O₂ / 16 h / 25 °C

2.3: 49 percent / NaOH / methanol / 3 h / 20 °C

With formic acid; toluene-4-sulfonic acid; In 1,4-dioxane;

DOI:10.1039/b505069c

upstream raw materials:

stigmast-5-en-3-yl acetate

β-sitosterol

dihydrogen peroxide

acetic acid

Downstream raw materials:

stigmast-4-ene-3,6-dione

(24R)-3β,5α-dihydroxy-24-ethyl-5α-cholestan-6-one

stigmastan-3,6-dione

Refernces

• 1、 McCarthy, Florence O.,Chopra, Jay,Ford, Alan,Hogan, Sean A.,Kerry, Joe P.,O'Brien, Nora M.,Ryan, Eileen,Maguire, Anita R.. "Synthesis, isolation and characterisation of β-sitosterol and β-sitosterol oxide derivatives". . p. 3059 - 3065. Retrieved 2007/10/03.
• 2、 Kovganko, N. V.,Kashkan, Zh. N.. "SYNTHESIS OF NATURAL PHYTOSTEROIDS OF THE 6-KETOSTIGMASTANE SERIES AND COMPOUNDS RELATED TO THEM". . p. 656 - 660. Retrieved 2007/10/02.