7alpha,17beta-Dihydroxyandrost-4-en-3-one

Base Information

• Chemical Name: 7alpha,17beta-Dihydroxyandrost-4-en-3-one
• CAS No.: 62-83-9
• Molecular Formula: C₁₉H₂₈O₃
• Molecular Weight: 304.43
• NSC Number: 51179
• DSSTox Substance ID: DTXSID50977536
• Mol file: 62-83-9.mol

Synonyms:7-hydroxytestosterone;7-hydroxytestosterone, (7beta,17beta)-isomer

Chemical Property of 7alpha,17beta-Dihydroxyandrost-4-en-3-one

Chemical Property:

• Vapor Pressure: 3.84E-11mmHg at 25°C
• Melting Point: 218-220 °C
• Boiling Point: 478°C at 760 mmHg
• PKA: 14.40±0.70(Predicted)
• Flash Point: 257°C
• PSA: 57.53000
• Density: 1.19g/cm³
• LogP: 2.85000
• Storage Temp.: 2-8°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 304.20384475
• Heavy Atom Count: 22
• Complexity: 539

Purity/Quality:

99.5% ^*data from raw suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 61-40
• Safety Statements: 53-22-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2O)C(CC4=CC(=O)CCC34C)O
• Uses: 7α-Hydroxytestosterone, is a metabolite of Testosterone (T155000), a principal hormone of the testes, produced by the interstitial cells.

Technology Process of 7alpha,17beta-Dihydroxyandrost-4-en-3-one

There total 9 articles about 7alpha,17beta-Dihydroxyandrost-4-en-3-one 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: 35.0%

testosterone (58-22-0) → 12,15α-dihydroxymethyltestosterone + 15alpha-Hydroxytestosterone (2226-70-2) + 7α,17β-dihydroxyandrost-4-en-3-one (62-83-9,969-13-1)

Guidance literature:

With D-glucose; In water; at 25 ℃; for 120h;

DOI:10.1007/s10600-011-9830-7

Reference yield:

5-androstenediol (521-17-5,1963-03-7,4593-57-1,4593-58-2,14504-94-0,16895-59-3,47122-33-8,64162-67-0,75767-22-5,139973-51-6,151284-19-4) → 3β,7α-dihydroxyandrost-5-ene-17-one (2487-48-1,7522-54-5,62357-03-3,53-00-9) + 7α,17β-dihydroxyandrost-4-en-3-one (62-83-9,969-13-1) + 3β,14α,17β-trihydroxyandrost-5-en-7-one + 3β,5β,6α,7α,17β-pentahydroxyandrostane + 3β,5α,6β,7α,17β-pentahydroxyandrostane + 3β,5α,6β,7β,17β-pentahydroxyandrostane + 3β,5α,6β,11α,17β-pentahydroxyandrostane + 3β,5α,6β,15β,17β-pentahydroxyandrostane + 3β,5α,6β,14α,17β-pentahydroxyandrostane + Androst-5-ene-3beta,7alpha,17beta-triol (2697-85-0,62357-04-4,2226-66-6) + 5-androstene-3β,7β,17β-triol (2697-85-0)

Guidance literature:

With water; In ethanol; for 120h; Microbiological reaction;

DOI:10.1016/j.molcatb.2015.11.026

Reference yield:

dehydroepiandrosterone (53-43-0) → 3β,7α-dihydroxyandrost-5-ene-17-one (2487-48-1,7522-54-5,62357-03-3,53-00-9) + 7α,17β-dihydroxyandrost-4-en-3-one (62-83-9,969-13-1) + 3β,14α,17β-trihydroxyandrost-5-en-7-one + 3β,5β,6α,7α,17β-pentahydroxyandrostane + 3β,5α,6β,7α,17β-pentahydroxyandrostane + 3β,5α,6β,7β,17β-pentahydroxyandrostane + 3β,5α,6β,11α,17β-pentahydroxyandrostane + 3β,5α,6β,15β,17β-pentahydroxyandrostane + 3β,5α,6β,14α,17β-pentahydroxyandrostane + Androst-5-ene-3beta,7alpha,17beta-triol (2697-85-0,62357-04-4,2226-66-6) + 5-androstene-3β,7β,17β-triol (2697-85-0)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium tetrahydroborate / methanol

2: water / ethanol / 120 h / Microbiological reaction

With sodium tetrahydroborate; water; In methanol; ethanol;

DOI:10.1016/j.molcatb.2015.11.026

upstream raw materials:

testosterone

Androstenedione

5-androstenediol

dehydroepiandrosterone

Downstream raw materials:

7α-hydroxy-1-dehydrotestosterone

Refernces

• 1、 Janeczko, Tomasz,Swizdor, Alina,Dmochowska-Gladysz, Jadwiga,Bialonska, Agata,Ciunik, Zbigniew,Kostrzewa-Suslow, Edyta. "Novel metabolites of dehydroepiandrosterone and progesterone obtained in Didymosphearia igniaria KCH 6670 culture". experimental part. p. 24 - 31. Retrieved 2012/10/08.
• 2、 Eechaute,Lacroix,Leusen. "Kinetic study of HCG induced decrease of microsomal 7α-hydroxylase activity in rat testes". . p. 647 - 660. Retrieved 2007/10/02.