Etiocholanolone

Base Information

• Chemical Name: Etiocholanolone
• CAS No.: 53-42-9
• Molecular Formula: C19H30O2
• Molecular Weight: 290.446
• NSC Number: 50908
• UNII: 97CGB1M48I
• DSSTox Substance ID: DTXSID001018919
• Nikkaji Number: J4.146G
• Wikipedia: Etiocholanolone
• Wikidata: Q5404598
• NCI Thesaurus Code: C29023
• Pharos Ligand ID: FSKQCXZNC9M9
• Metabolomics Workbench ID: 35341
• ChEMBL ID: CHEMBL85799
• Mol file: 53-42-9.mol

Synonyms:3 alpha Hydroxy 5 beta Androstan 17 One;3-alpha-Hydroxy-5-beta-Androstan-17-One;5 beta Androsterone;5-beta-Androsterone;Etiocholanolone

Chemical Property of Etiocholanolone

Chemical Property:

• Vapor Pressure: 1.5E-08mmHg at 25°C
• Melting Point: 148～150℃
• Refractive Index: 1.536
• Boiling Point: 413.1°Cat760mmHg
• PKA: 15.14±0.60(Predicted)
• Flash Point: 176.4°C
• PSA: 37.30000
• Density: 1.085g/cm³
• LogP: 3.95910
• Storage Temp.: 2-8°C
• Water Solubility.: 20.33mg/L(25 oC)
• 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:

97% ^*data from raw suppliers

Etiocholan-3α-ol-17-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xn
• Hazard Codes: F,Xn
• Statements: 11-20/21/22-36
• Safety Statements: 16-36/37

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
• Uses: 5β-Androsterone is a metabolite of Testosterone (T155000). β-Androsterone is a stereoisomer of Androsterone (A637535). 5β-Androsterone showed a weak estrogenic action.

Technology Process of Etiocholanolone

There total 42 articles about Etiocholanolone 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: 96.0%

Androsterone-dimethyl-tert.-butylsilyl-ether (57711-44-1,57711-45-2,65598-73-4,65598-74-5) → (3R,10S,13S)-3-Hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-one (53-41-8,53-42-9,481-28-7,481-29-8,571-30-2,571-31-3,6030-68-8,6247-88-7,19778-17-7,19778-18-8,20120-02-9,20120-07-4,20120-08-5,20783-88-4,34864-66-9,36378-51-5,52746-44-8,84416-35-3,102207-98-7,145918-93-0)

Guidance literature:

With Povidone-Iodine; In methanol; at 30 ℃; for 1h;

DOI:10.1016/j.tetlet.2019.05.059

Reference yield: 58.2%

androstane-3,17-dione (1229-12-5) → Etiocholanolone (53-42-9) + Epietiocholanolone (571-31-3)

Guidance literature:

With trimethylamine-borane; silica gel; iron(III) chloride; In benzene; for 2h; Ambient temperature;

DOI:10.1246/cl.1986.61

Reference yield: 6.0%

Progesterone (57-83-0) → testosterone (58-22-0) + Androstenedione (63-05-8) + Etiocholanolone (53-42-9) + androstane-3,17-dione (1229-12-5)

Guidance literature:

With Aspergillus aureofulgens; In acetone; at 25 ℃; for 24h; pH = 7.5;

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:

androstane-3,17-dione

5β-androstane-3α,17β-diol

5beta-Androstane-3alpha,17alpha-diol

5beta-Androstan-3alpha-ol