Epietiocholanolone

Base Information

• Chemical Name: Epietiocholanolone
• CAS No.: 571-31-3
• Molecular Formula: C19H30O2
• Molecular Weight: 290.446
• NSC Number: 62996
• UNII: C1751JYC6P
• DSSTox Substance ID: DTXSID601024073
• Nikkaji Number: J39.820I
• Wikipedia: Epietiocholanolone
• Wikidata: Q27161719
• Metabolomics Workbench ID: 35382
• ChEMBL ID: CHEMBL260526
• Mol file: 571-31-3.mol

Synonyms:Epietiocholanolone;571-31-3;3beta-hydroxy-5beta-androstan-17-one;5beta-androstan-3beta-ol-17-one;beta-Etiocholanolone;3.beta.-Etiocholanolone;epi-5.beta.-androsterone;NSC-62996;C1751JYC6P;Etiocholan-3.beta.-ol-17-one;CHEBI:89524;(3S,5R,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one;J39.820I;3b-hydroxy-5b-androstan-17-one;5.beta.-Epiandrosterone;5.beta.-Androstan-17-one, 3.beta.-hydroxy-;3.beta.-Hydroxyetiocholan-17-one;b-Etiocholanolone;Methyl-1-alpha;Epiaetiocholanolone;3b-Etiocholanolone;5b-Epiandrosterone;epi-5b-Androsterone;3beta-Etiocholanolone;3.beta.-Hydroxy-5.beta.-androstane-17-one;Epi-5beta-androsterone;Androstan-17-one, 3-hydroxy-, (3.beta.,5.beta.)-;Etiocholan-3b-ol-17-one;UNII-C1751JYC6P;3b-Hydroxyetiocholan-17-one;Etiocholan-3beta-ol-17-one;MLS000563094;.BETA.-ETIOCHOLANOLONE;5b-Androstan-3b-ol-17-one;5b-Androstane-3b-ol-17-one;CHEMBL260526;SCHEMBL5951521;3b-Hydroxy-17-oxo-5b-androstane;3b-Hydroxy-5b-androstane-17-one;DTXSID601024073;HMS2271P11;NSC62996;BDBM50375560;LMST02020104;5-beta-Androstan-3-beta-ol-17-one;AKOS027381609;CS-I-00054;5beta-Androstan-17-one, 3beta-hydroxy-;SMR001215856;Androstan-17-one, (3.beta.,5.beta.)-;A903385;Androstan-17-one, 3-hydroxy-, (3beta,5beta)-;3.BETA.-HYDROXY-5.BETA.-ANDROSTAN-17-ONE;Q27161719;(3aS,3bR,5aR,7S,9aS,9bS,11aS)-7-hydroxy-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-1-one;(3S,5R,8R,10S,13S)-3-Hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-one;(3S,5R,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethylhexadecahydro-17H-cyclopenta[a]phenanthren-17-one

Chemical Property of Epietiocholanolone

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 1.5E-08mmHg at 25°C
• Melting Point: 154-156 ºC
• Refractive Index: 1.536
• Boiling Point: 413.1 °C at 760 mmHg
• Flash Point: 176.4 °C
• PSA: 37.30000
• Density: 1.085 g/cm³
• LogP: 3.95910
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 290.224580195
• Heavy Atom Count: 21
• Complexity: 459

Purity/Quality:

99%, ^*data from raw suppliers

5β-Androstan-3β-ol-17-one(Solution) ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(CC1CCC3C2CCC4(C3CCC4=O)C)O
• Isomeric SMILES: C[C@]12CC[C@@H](C[C@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CCC4=O)C)O

Technology Process of Epietiocholanolone

There total 40 articles about Epietiocholanolone 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: 98.5%

3β-acetoxy-5β-androstan-17-one (4820-41-1) → Epietiocholanolone (571-31-3)

Guidance literature:

With sodium hydroxide; In methanol; water;

Reference yield: 95.0%

16α-bromo-3β-hydroxyandrostan-17-one → Epietiocholanolone (571-31-3)

Guidance literature:

With hydrogen iodide; for 3h; Ambient temperature;

DOI:10.1080/00397919308011227

Reference yield: 91.0%

(3β,5β)-17-(1,3-dioxolan-2-yl)-3-hydroxyandrostane (5717-77-1) → Epietiocholanolone (571-31-3)

Guidance literature:

With toluene-4-sulfonic acid; In acetone; for 6h;

DOI:10.1021/jo00171a018

upstream raw materials:

(3S,5S,10S,13S)-10,13-Dimethyl-hexadecahydro-cyclopenta[a]phenanthrene-3,17-diol

C₂₁H₃₄OS₂

androstendione

Androsterone-dimethyl-tert.-butylsilyl-ether

Downstream raw materials:

Formic acid (3S,5R,8R,9S,10S,13S,14S)-10,13-dimethyl-17-oxo-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester

3β-hydroxy-5β-androstan-17-one 3-tetrahydropyranyl ether

16ξ-phenylsulfinyl-3β-phenylsylfinyloxy-5β-androstan-17-one

androstane-3,17-dione

Refernces

• 1、 Ke, Yanxiong,Lu, Guangying,Ren, Jiangmeng,Wang, Di,Zeng, Bu-Bing. "Catalytic removal of tert-butyldimethylsilyl (TBS) ether by PVP-I". . . Retrieved 2019/09/06.
• 2、 Endo, Satoshi,Matsunaga, Toshiyuki,Kumada, Sho,Fujimoto, Airi,Hara, Akira,Ohno, Satoshi,El-Kabbani, Ossama,Hu, Dawei,Toyooka, Naoki,Mano, Jun'Ichi,Tajima, Kazuo. "Characterization of rabbit aldose reductase-like protein with 3β-hydroxysteroid dehydrogenase activity". . p. 23 - 30,8. Retrieved 2020/08/20.