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

Base Information

• Chemical Name: Androst-4-ene-3,6,17-trione
• CAS No.: 2243-06-3
• Molecular Formula: C19H24O3
• Molecular Weight: 300.398
• UNII: L8L0381OBP
• DSSTox Substance ID: DTXSID60862888
• Nikkaji Number: J352.701H
• Wikipedia: 4-Androstene-3,6,17-trione
• Wikidata: Q4637100
• Mol file: 2243-06-3.mol

Synonyms:4-androstene-3,6,17-trione;6-oxo-androstenedione;6-oxoandrostenedione;androst-4-ene-3,6,17-trione

Chemical Property of Androst-4-ene-3,6,17-trione

Chemical Property:

• Appearance/Colour: Yellow solid
• Vapor Pressure: 1.2E-08mmHg at 25°C
• Melting Point: 223-224 °C
• Refractive Index: 1.56
• Boiling Point: 460.044 °C at 760 mmHg
• Flash Point: 198.465 °C
• PSA: 51.21000
• Density: 1.188 g/cm³
• LogP: 3.26640
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly, Heated)
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 300.17254462
• Heavy Atom Count: 22
• Complexity: 616

Purity/Quality:

99% ^*data from raw suppliers

Androst-4-ene-3,6,17-trione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2=O)CC(=O)C4=CC(=O)CCC34C
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CC(=O)C4=CC(=O)CC[C@]34C
• Uses: An aromatase inhibitor

Technology Process of Androst-4-ene-3,6,17-trione

There total 45 articles about Androst-4-ene-3,6,17-trione 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: 90.0%

4α-ethylthio-5α-androstane-3,6,17-trione (103232-92-4) → androst-4-ene-3,6,17-trione (2243-06-3)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In ethyl acetate; for 9h; Ambient temperature;

Reference yield: 89.0%

5α-hydroxyandrostane-3,6,17-trione (74395-56-5) → androst-4-ene-3,6,17-trione (2243-06-3)

Guidance literature:

With sulfuric acid; water; In ethanol; for 3.5h; Reflux;

DOI:10.1134/S1070363217110196

Reference yield: 89.0%

dehydroepiandrosterone (53-43-0) → androst-4-ene-3,6,17-trione (2243-06-3)

Guidance literature:

With Montmorillonite K₁₀; pyridinium chlorochromate; In 1,4-dioxane; for 0.75h; Irradiation;

DOI:10.1016/S0040-4020(98)01138-7

upstream raw materials:

dehydroepiandrosterone

6β-hydroxytestosterone

6β,17α,21-trihydroxypregn-4-ene-3,20-dione

3β,6β-dihydroxyandrost-4-en-17-one

Downstream raw materials:

3-[O-(2-aminoethyl)oxime]-(5α)-androstene-3,6,17-trione

androst-4-ene-6,17-dione

androsta-3,5-dien-17-one

6-ketoestradiol

Refernces

• 1、 Parish,Kizito,Heidepriem. "A novel synthesis of steroidal Δ4,3,6-diones using pyridinium chlorochromate (PCC)". . p. 223 - 230. Retrieved 1993.
• 2、 Blaszczyk,Paryzek. "Oxidation of homoallylic steroidal alcohols with pyridinium chlorochromate. The synthesis of steroidal 4-en-3,6-diones". . p. 3255 - 3259. Retrieved 1994.
• 3、 Miranda Moreno,Sa E Melo,Campos Neves. "A novel oxidation of homoallylic alcohols under sonochemical conditions". . p. 3201 - 3204. Retrieved 1991.
• 4、 Holland, Herbert L.,Daum, Ulrich,Riemland, Elly. "OXIDATION WITH SODIUM PEROXIDE. DIRECT INTRODUCTION OF A γ CARBONYL GROUP INTO α,β UNSATURATED KETOSTEROIDS". . p. 5127 - 5128. Retrieved 1981.
• 5、 Nangia,Anthony. "Facile synthesis of steroidal Δ4-3,6-diones from Δ5-3-ols using pyridinium chlorochromate". . p. 225 - 230. Retrieved 1996.
• 6、 Shinriki,Nambara. "Analytical chemical studies on steroids. XLV. Polarographic behaviors of androst-4-ene-3,6,17-trione.". . p. 611 - 617. Retrieved 1971.
• 7、 Campos Neves, Andre S.,Sa E Melo, Maria Luisa,Moreno, Maria Jose S. M.,Tavares Da Silva, Elisiario J.,Salvador, Jorge A. R.,Da Costa, Saul P.,Martins, Rosa Maria L. M.. "Improved syntheses of aromatase inhibitors and neuroactive steroids efficient oxidations and reductions at key positions for bioactivity". . p. 3255 - 3264. Retrieved 1999.
• 8、 -. "Novel synthesis method of Istaroxime". . . Retrieved 2016/10/10.