Androstenedione

Base Information

• Chemical Name: Androstenedione
• CAS No.: 63-05-8
• Deprecated CAS: 104534-78-3,117598-81-9,1050678-87-9,117598-81-9,846024-35-9
• Molecular Formula: C19H26O2
• Molecular Weight: 286.414
• Hs Code.: 29372900
• European Community (EC) Number: 200-554-5
• NSC Number: 9563
• UNII: 409J2J96VR
• DSSTox Substance ID: DTXSID8024523
• Nikkaji Number: J38.388K
• Wikipedia: Androstenedione
• Wikidata: Q411064
• NCI Thesaurus Code: C244,C2300
• Pharos Ligand ID: FSFMVRT8XQ4Z
• Metabolomics Workbench ID: 35317
• ChEMBL ID: CHEMBL274826
• Mol file: 63-05-8.mol

Synonyms:4 Androstene 3,17 dione;4-Androstene-3,17-dione;Androstenedione;delta 4 Androstenedione;delta-4-Androstenedione

Chemical Property of Androstenedione

Chemical Property:

• Appearance/Colour: white to off-white solid
• Vapor Pressure: 1.2E-07mmHg at 25°C
• Melting Point: 170-171 °C(lit.)
• Refractive Index: 1.551
• Boiling Point: 431.4 °C at 760 mmHg
• Flash Point: 161.1 °C
• PSA: 34.14000
• Density: 1.11 g/cm³
• LogP: 4.08740
• Storage Temp.: Controlled Substance, -20°C Freezer
• Water Solubility.: 57.28mg/L(25 oC)
• XLogP3: 2.7
• 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

Androstenedione solution 1.0?mg/mL in acetonitrile, ampule of 1?mL, certified reference material, Cerilliant? ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,T,F
• Statements: 40-64-52-22-61-60-36-20/21/22-11
• Safety Statements: 22-24/25-36-45-36/37-53-26-16

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(=O)C=C1CCC3C2CCC4(C3CCC4=O)C
• Isomeric SMILES: C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CCC4=O)C
• Description: Androstenedione (CRM) (Item No. ISO60161) is a certified reference material categorized as an anabolic androgenic steroid. Androstenedione is a precursor of testosterone (Item Nos. ISO60154 | ISO00154 | 15645) and estrone . Androstenedione is regulated as a Schedule III compound in the United States. Androstenedione (CRM) (Item No. ISO60161) is provided as a DEA exempt preparation. This product is intended for research and forensic applications.
• Uses: Testosterone precursor and metabolite with androgenic activity. Controlled substance (anabolic sterid)

Technology Process of Androstenedione

There total 241 articles about Androstenedione 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: 53.0%

dehydroepiandrosterone (53-43-0) → Androstenedione (63-05-8) + 5-androstenedione (571-36-8)

Guidance literature:

With Celite; pyridinium chlorochromate; In dichloromethane; for 3.5h; Yields of byproduct given; Ambient temperature;

DOI:10.1021/jo952202x

Reference yield: 16.3%

testosterone (58-22-0) → Epiandrosterone (481-29-8) + Androstenedione (63-05-8) + cis-androsterone (53-41-8) + androstanedione (846-46-8)

Guidance literature:

With Penicillium digitatum MRC 500787; MYB medium (malt extract 2percent, glucose 1percent, bacteriological peptone 1percent, yeast extract 0.3percent); In N,N-dimethyl-formamide; at 24 ℃; for 120h;

DOI:10.1135/cccc2009550

Reference yield: 6.0%

cholesterol (57-88-5) → dehydroepiandrosterone (53-43-0) + Androstenedione (63-05-8)

Guidance literature:

With [2,2]bipyridinyl; Cephalosporium longisporum; Micrococcus sp; Pseudomonas stutzeri; at 29 ℃; for 72h;

upstream raw materials:

testosterone

dehydroepiandrosterone

17-hydroxyprogesterone

5-androstenediol

Downstream raw materials:

16-dehydroprogesterone

testosterone

epitestosterone

9-alpha-hydroxyandrost-4-ene-3,17-dione

Refernces

• 1、 Tars, Kaspars,Olin, Birgit,Mannervik, Bengt. "Structural Basis for Featuring of Steroid Isomerase Activity in Alpha Class Glutathione Transferases". . p. 332 - 340. Retrieved 2010.
• 2、 Perera, S. K.,Dunn, W. A.,Fedor, L. R.. "Acid- and Base-Catalyzed Isomerization of Androst-5-ene-3,17-dione and 17α-Ethynyl-17β-hydroxy-5-estren-3-one". . p. 2816 - 2821. Retrieved 1980.
• 3、 Reisch,Ekiz,Takacs. "Photochemical studies LII: investigation on the photostability of testosterone and methyltestosterone in the solid state". . p. 173 - 175. Retrieved 1989.
• 4、 Kuenzer, H.,Stahnke, M.,Sauer, G.,Wiechert, R.. "REGIO- AND STEREOSELECTIVE 1,4-REDUCTIONS OF METHYLATED, CROSS-CONJUGATED STEROIDAL CYCLOHEXADIENONES". . p. 3859 - 3862. Retrieved 1990.
• 5、 Fejedelem, Zachary,Carney, Nolan,Nagorny, Pavel. "Synthesis of Cardiotonic Steroids Oleandrigenin and Rhodexin B". . p. 10249 - 10262. Retrieved 2021/07/31.
• 6、 Chen, Ming,Dong, Guangbin. "Platinum-Catalyzed α,β-Desaturation of Cyclic Ketones through Direct Metal–Enolate Formation". supporting information. p. 7956 - 7961. Retrieved 2021/03/01.