Varanic acid

Base Information

• Chemical Name: Varanic acid
• CAS No.: 1061-64-9
• Molecular Formula: C₂₇H₄₆O₆
• Molecular Weight: 466.659
• DSSTox Substance ID: DTXSID901318051
• Nikkaji Number: J639.989D
• Wikidata: Q27121366
• Metabolomics Workbench ID: 75106
• Mol file: 1061-64-9.mol

Synonyms:3 alpha,7 alpha,12 alpha,24-tetrahydroxy-5 beta-cholestanoic acid;3,7,12,24-tetrahydroxycholestanoic acid;3alpha,7alpha,12alpha,24-tetrahydroxy-5beta-cholestan-26-oic acid;TTHCA;varanic acid

Chemical Property of Varanic acid

Chemical Property:

• Vapor Pressure: 5.47E-19mmHg at 25°C
• Boiling Point: 638.4°Cat760mmHg
• Flash Point: 353.9°C
• PSA: 118.22000
• Density: 1.188g/cm³
• LogP: 3.44570
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 466.32943918
• Heavy Atom Count: 33
• Complexity: 727

Purity/Quality:

98%,99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCC(C(C)C(=O)O)O)C1CCC2C1(C(CC3C2C(CC4C3(CCC(C4)O)C)O)O)C
• Isomeric SMILES: C[C@H](CCC(C(C)C(=O)O)O)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2[C@@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)O)C

Technology Process of Varanic acid

There total 8 articles about Varanic acid 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:

cholic acid (81-25-4) → 3α,7α,12α,24ξ-tetrahydroxy-5β-cholestan-26-oic acid (1061-64-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.65 g / p-TosOH / 2 h / Ambient temperature

2: 0.42 g / diborane / tetrahydrofuran / 0.08 h / -5 °C

3: 0.37 g / pyridinium chlorochromate / CH₂Cl₂ / 2.5 h / Ambient temperature

With toluene-4-sulfonic acid; pyridinium chlorochromate; diborane; In tetrahydrofuran; dichloromethane;

DOI:10.1016/0039-128X(82)90140-4

Reference yield:

(3α,5β,7α,12α)-3,7,12-tris(formyloxy)cholan-24-oyl chloride (74670-08-9) → 3α,7α,12α,24ξ-tetrahydroxy-5β-cholestan-26-oic acid (1061-64-9)

Guidance literature:

Multi-step reaction with 2 steps

1: tetramethylammonium hydridoirontetracarbonyl / CH₂Cl₂ / 4 h / Ambient temperature

2: 1) Zn, I₂, Cu, 2) 10percent KOH / 1) toluene, reflux, 5 h, 2) ethanol, 3 h

With potassium hydroxide; tetramethylammonium hydridoirontetracarbonyl; iodine; copper; zinc; In dichloromethane;

DOI:10.1016/0039-128X(82)90140-4

Reference yield:

cholic acid triformate (2097-89-4) → 3α,7α,12α,24ξ-tetrahydroxy-5β-cholestan-26-oic acid (1061-64-9)

Guidance literature:

Multi-step reaction with 3 steps

1: SOCl₂ / benzene / 2 h / Ambient temperature

2: tetramethylammonium hydridoirontetracarbonyl / CH₂Cl₂ / 4 h / Ambient temperature

3: 1) Zn, I₂, Cu, 2) 10percent KOH / 1) toluene, reflux, 5 h, 2) ethanol, 3 h

With potassium hydroxide; thionyl chloride; tetramethylammonium hydridoirontetracarbonyl; iodine; copper; zinc; In dichloromethane; benzene;

DOI:10.1016/0039-128X(82)90140-4

upstream raw materials:

3α,7α,12α-triformyloxy-5β-cholan-24-al

Ethyl 2-bromopropionate

3α,7α,12α-tris[(tetrahydropyran-2-yl)oxy]-5β-cholan-24-al

cholic acid

Downstream raw materials:

dehydrocholic acid

p-bromophenacyl (24S,25S)-3α,7α,12α,24-tetrahydroxy-5β-cholestan-26-oate

p-bromophenacyl (24S,25R)-3α,7α,12α,24-tetrahydroxy-5β-cholestan-26-oate

p-bromophenacyl (24R,25S)-3α,7α,12α,24-tetrahydroxy-5β-cholestan-26-oate