Androstenediol

Base Information

• Chemical Name: Androstenediol
• CAS No.: 521-17-5
• Molecular Formula: C₁₉H₃₀O₂
• Molecular Weight: 290.446
• Hs Code.: 29061990
• European Community (EC) Number: 208-306-8
• UNII: 95PS51EMXY
• DSSTox Substance ID: DTXSID9022609
• Nikkaji Number: J6.611G
• Wikipedia: Androstenediol
• Wikidata: Q2817108
• NCI Thesaurus Code: C95979
• Pharos Ligand ID: FS5872XQD4ZV
• Metabolomics Workbench ID: 35315
• ChEMBL ID: CHEMBL440283
• Mol file: 521-17-5.mol

Synonyms:5 Androstene 3,17 diol;5 Androstene 3beta 17beta Diol;5-Androstene-3,17-diol;5-Androstene-3beta-17beta-Diol;Androst 5 ene 3 beta,17 beta Diol;Androst 5 ene 3,17 diol;Androst-5-ene-3 beta,17 beta-Diol;Androst-5-ene-3,17-diol;Androstenediol;Bisexovister;delta 5 Androstene 3 beta,17 beta Diol;Delta 5 Androstenediol;delta 5-Androstene-3 beta,17 beta-Diol;Delta 5-Androstenediol;Hermaphrodiol

Chemical Property of Androstenediol

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: 178-182 °C
• Boiling Point: 428.4 °C at 760 mmHg
• PKA: 15.01±0.70(Predicted)
• Flash Point: 194.5 °C
• PSA: 40.46000
• Density: 1.12 g/cm³
• LogP: 3.67100
• Storage Temp.: 2-8°C
• XLogP3: 3.5
• 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

Androstenediol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,T
• Hazard Codes: F,T
• Statements: 60-61-11-19-38
• Safety Statements: 24/25-45-53

MSDS Files:

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2O)CC=C4C3(CCC(C4)O)C
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CC=C4[C@@]3(CC[C@@H](C4)O)C
• Uses: Androstenediol is used for weight training and recovery, and to increase testosterone production and stamina.

Technology Process of Androstenediol

There total 50 articles about Androstenediol 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: 99.0%

prasterone acetate (853-23-6) → 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)

Guidance literature:

With diisobutylaluminium hydride; nickel dichloride; In dichloromethane; toluene; at -78 ℃; for 0.25h; Inert atmosphere;

DOI:10.3184/174751911X13050949941793

Reference yield: 94.0%

dehydroepiandrosterone (53-43-0) → 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)

Guidance literature:

With sodium tetrahydroborate; TiO(acac)2; In tetrahydrofuran; for 2.5h; Heating;

DOI:10.1515/znb-2003-1211

Reference yield: 83.0%

androstane-3,5-dien-17-one-3β-ol acetate (4968-05-2) → 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)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 - 22 ℃;

upstream raw materials:

dehydroepiandrosterone

ethylmagnesium iodide

diethyl ether

dehydroepiandrosterone

Downstream raw materials:

3β.17β-bis-(4-nitro-benzoyloxy)-androstene-(5)

testosterone

Androstenedione

5-androstenedione

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 2019/04/26.
• 2、 Pitts, Cody Ross,Bume, Desta Doro,Harry, Stefan Andrew,Siegler, Maxime A.,Lectka, Thomas. "Multiple Enone-Directed Reactivity Modes Lead to the Selective Photochemical Fluorination of Polycyclic Terpenoid Derivatives". supporting information. p. 2208 - 2211. Retrieved 2017/02/23.