Androst-5-ene-3,17-dione

Base Information

• Chemical Name: Androst-5-ene-3,17-dione
• CAS No.: 571-36-8
• Molecular Formula: C19H26O2
• Molecular Weight: 286.414
• NSC Number: 12873
• UNII: HEE11L5C3G
• DSSTox Substance ID: DTXSID10862217
• Nikkaji Number: J79.661A
• Wikipedia: 5-Androstenedione
• Wikidata: Q15277399
• Metabolomics Workbench ID: 146112
• ChEMBL ID: CHEMBL1743203
• Mol file: 571-36-8.mol

Synonyms:5-androstene-3,17-dione

Chemical Property of Androst-5-ene-3,17-dione

Chemical Property:

• Vapor Pressure: 2.19E-07mmHg at 25°C
• Melting Point: 158 °C
• Refractive Index: 1.551
• Boiling Point: 423.7 °C at 760 mmHg
• Flash Point: 158.4 °C
• PSA: 34.14000
• Density: 1.11 g/cm³
• LogP: 4.08740
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 286.193280068
• Heavy Atom Count: 21
• Complexity: 546

Purity/Quality:

99%, ^*data from raw suppliers

5-ANDROSTENE-3,17-DIONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2=O)CC=C4C3(CCC(=O)C4)C
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CC=C4[C@@]3(CCC(=O)C4)C

Technology Process of Androst-5-ene-3,17-dione

There total 18 articles about Androst-5-ene-3,17-dione 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: 85.0%

dehydroepiandrosterone (53-43-0) → 5-androstenedione (571-36-8)

Guidance literature:

DOI:10.1016/j.bmcl.2010.10.112

Reference yield: 84.0%

androst-5-ene-3β,17β-diol (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) → Δ5-Androsten-3,17-dion (571-36-8)

Guidance literature:

With 4 A molecular sieve; pyridinium chlorochromate; calcium carbonate; In dichloromethane; at 25 ℃; for 0.5h;

DOI:10.1080/00397919208021550

Reference yield: 83.0%

Androstenedione (63-05-8) → 5-androstenedione (571-36-8)

Guidance literature:

Androstenedione; With potassium tert-butylate; In tert-butyl alcohol; at 35 - 40 ℃; for 1.5h; Inert atmosphere;

With acetic acid; In water; tert-butyl alcohol; at 20 - 25 ℃; Temperature; Reagent/catalyst;

upstream raw materials:

3ξ-hydroxy-androst-5-en-17-one

androst-5-ene-3β,17β-diol

androst-5-ene-3β,17β-diol

dehydroepiandrosterone

Downstream raw materials:

Androstenedione

androst-4-ene-3,6,17-trione

prasterone acetate

dehydroepiandrosterone p-nitrobenzoate

Refernces

• 1、 Yao, Zhiyi,Xu, Yingjun,Zhang, Minmin,Jiang, Sheng,Nicklaus, Marc C.,Liao, Chenzhong. "Discovery of a novel hybrid from finasteride and epristeride as 5α-reductase inhibitor". . p. 475 - 478. Retrieved 2011.
• 2、 Houck, Wendy J.,Pollack, Ralph M.. "Temperature effects on the catalytic activity of the D38E mutant of 3-Oxo-Δ5-steroid isomerase: Favorable enthalpies and entropies of activation relative to the nonenzymatic reaction catalyzed by acetate ion". . p. 16416 - 16425. Retrieved 2004.
• 3、 Houck, Wendy J.,Pollack, Ralph M.. "Activation enthalpies and entropies for the microscopic rate constants of acetate-catalyzed isomerization of 5-androstene-3,17-dione". . p. 10206 - 10212. Retrieved 2003.
• 4、 Zeng,Pollack. "Microscopic rate constants for the acetate ion catalyzed isomerization of 5-androstene-3,17-dione to 4-androstene-3,17-dione: a model for steroid isomerase". . p. 3838 - 3842. Retrieved 1991.
• 5、 Fryszkowska, Anna,Peterson, Justine,Davies, Nichola L.,Dewar, Colin,Evans, George,Bycroft, Matthew,Triggs, Neil,Fleming, Toni,Gorantla, Srikanth Sarat Chandra,Hoge, Garrett,Quirmbach, Michael,Timmanna, Upadhya,Reddy Poreddy, Srinivas,Kumar Reddy, D. Naresh,Dahanukar, Vilas,Holt-Tiffin, Karen E.. "Development of a Chemoenzymatic Process for Dehydroepiandrosterone Acetate Synthesis". . p. 1520 - 1528. Retrieved 2016/08/30.
• 6、 -. "PROCESSES FOR THE PREPARATION OF DEHYDROEPIANDROSTERONE AND ITS INTERMEDIATES". Page/Page column 19; 20. . Retrieved 2014/12/12.