Androst-4-ene-3,17-diol

Base Information

• Chemical Name: Androst-4-ene-3,17-diol
• CAS No.: 1156-92-9
• Molecular Formula: C19H30O2
• Molecular Weight: 290.446
• Hs Code.: 29372900
• European Community (EC) Number: 641-983-1
• Nikkaji Number: J1.483.935F
• Wikipedia: 4-Androstenediol
• Mol file: 1156-92-9.mol

Synonyms:(3beta,17alpha)-4-androstene-3,17-diol;(3beta,17beta)-4-androstene-3,17-diol;4-androstene-3 alpha,17 beta-diol;4-androstene-3,17-diol;4-androstene-3,17-diol, T(-3)-4-(14)C-labeled;androst-4-ene-3,17-diol

Chemical Property of Androst-4-ene-3,17-diol

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: 155.5 °C
• Refractive Index: 1.571
• Boiling Point: 430.1 °C at 760 mmHg
• PKA: 14.38±0.70(Predicted)
• Flash Point: 195.5 °C
• PSA: 40.46000
• Density: 1.12 g/cm³
• LogP: 3.67100
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 290.224580195
• Heavy Atom Count: 21
• Complexity: 470

Purity/Quality:

99%, ^*data from raw suppliers

Androst-4-ene-3,17-diol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2O)CCC4=CC(CCC34C)O
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2O)CCC4=CC(CC[C@]34C)O

Technology Process of Androst-4-ene-3,17-diol

There total 29 articles about Androst-4-ene-3,17-diol 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: 91.0%

testosterone (58-22-0) → 4-androstenediol (1156-92-9)

Guidance literature:

With lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran;

DOI:10.1021/jo00172a060

Reference yield: 22.0%

testosterone (58-22-0) → 4-androstenediol (1156-92-9) + 4-Androstene-3alpha,17beta-diol (1852-61-5)

Guidance literature:

With lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; at 20 ℃; for 10.8333h; Reflux;

DOI:10.1021/jm300262w

Reference yield:

testosterone (58-22-0) → Stanolone (521-18-6) + 5β-androstan-17β-ol-3-one (571-22-2) + 5-androgen-3,17-diol (571-20-0) + 4-androstenediol (1156-92-9) + 4-Androstene-3alpha,17beta-diol (1852-61-5)

Guidance literature:

With H₂SiEt₂; Rh-(R,R)-(+)-DIOP; for 24h; Product distribution; other reducing agents;

DOI:10.1021/jo00248a028

upstream raw materials:

4-androstane-3β,17β-diol 3,17-diacetate

4-androstane-3β,17β-diol 17-acetate

4-androstene-3,17-dione

testosterone

Downstream raw materials:

Epiandrosterone

androstanedione

2-hydroxynitrobenzene

androst-3-en-3,17-dion

Refernces

• 1、 Roleira, Fernanda M. F.,Varela, Carla,Amaral, Cristina,Costa, Saul C.,Correia-Da-Silva, Georgina,Moraca, Federica,Costa, Giosuè,Alcaro, Stefano,Teixeira, Natércia A. A.,Tavares Da Silva, Elisiário J.. "C-6α- vs C-7α-Substituted Steroidal Aromatase Inhibitors: Which Is Better? Synthesis, Biochemical Evaluation, Docking Studies, and Structure-Activity Relationships". . p. 3636 - 3657. Retrieved 2019.
• 2、 Parish, Edward J.,Scott, Aubrey D.. "Selective Oxidation of Steroidal Allylic Alcohols Using 3,5-Dimethylpyrazole and Pyridinium Chlorochromate". . p. 4766 - 4768. Retrieved 1983.
• 3、 Braselton Jr,Orr,Engel. "Identification by gas chromatography mass spectrometry of intermediates in the aromatization of modified C19 steroids by human placental microsomes". . p. 411 - 433. Retrieved 1974.
• 4、 Butenandt,Tscherning,Hanisch. "-". . p. 2097,2100. Retrieved 1935.
• 5、 Pranata, Andy,Fitzgerald, Christopher C.,Khymenets, Olha,Westley, Erin,Anderson, Natasha J.,Ma, Paul,Pozo, Oscar J.,McLeod, Malcolm D.. "Synthesis of steroid bisglucuronide and sulfate glucuronide reference materials: Unearthing neglected treasures of steroid metabolism". supporting information. p. 25 - 40. Retrieved 2019/01/04.