Butenandt's acid

Base Information

• Chemical Name: Butenandt's acid
• CAS No.: 469-04-5
• Molecular Formula: C27H42 O5
• Molecular Weight: 446.627
• DSSTox Substance ID: DTXSID80963689
• Mol file: 469-04-5.mol

Synonyms:3-oxo-6,7-secocholest-4-ene 6,7-dioic acid;butenandt's acid

Chemical Property of Butenandt's acid

Chemical Property:

• Vapor Pressure: 6.39E-15mmHg at 25°C
• Boiling Point: 579.2°Cat760mmHg
• Flash Point: 318.1°C
• PSA: 91.67000
• Density: 1.113g/cm³
• LogP: 5.97230
• XLogP3: 6.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 446.30322444
• Heavy Atom Count: 32
• Complexity: 783

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)CCCC(C)C1CCC2C1(CCC(C2C(=O)O)C3(CCC(=O)C=C3C(=O)O)C)C
• Isomeric SMILES: C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CCC(C2C(=O)O)[C@]3(CCC(=O)C=C3C(=O)O)C)C

Technology Process of Butenandt's acid

There total 10 articles about Butenandt's 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: 47.9%

4-cholestene-3,6-dione (54339-68-3,984-84-9) → acide de Butenandt (469-04-5)

Guidance literature:

With oxygen; platinum; In tert-butyl alcohol; at 80 ℃; for 24h; under 15200 - 19000 Torr;

DOI:10.1246/bcsj.61.3023

Reference yield:

cholesterol (57-88-5) → acide de Butenandt (469-04-5)

Guidance literature:

With chromium(VI) oxide; acetic acid;

DOI:10.1021/ja01114a002

Reference yield:

cholesterol (57-88-5) → acide de Butenandt (469-04-5)

Guidance literature:

With sodium dichromate;

DOI:10.1021/ja01492a041

upstream raw materials:

cholesterol

4-cholestene-3,6-dione

Cholest-4-en-3β,6β-diol

cholesterol

Downstream raw materials:

dimethyl 3-oxo-6,7-seco-cholest-4-ene-6,7-dioate

acide dioxo-3,6 abeo 6(5->4) B-nor (10α) cholestene-1 carboxylique-1

(1R,3aS,4S,5S,7aR)-1-((R)-1,5-Dimethyl-hexyl)-5-((1R,4S)-4-hydroxy-2-methoxycarbonyl-1-methyl-cyclohex-2-enyl)-7a-methyl-octahydro-indene-4-carboxylic acid methyl ester

oxo-3 seco-6,7 cholestene-4 dioate-6,7 acide de ⁽⁷⁾ methyle

Refernces

• 1、 Sakamaki, Hiroshi,Take, Masa-aki,Akihisa, Toshihiro,Matsumoto, Taro,Ichinohe, Yoshiyuki. "Catalytic Oxygenation of Cholesterol with a Platinum Catalyst under Moderate Pressure of Oxygen". . p. 3023 - 3025. Retrieved 2007/10/02.