11alpha-Hydroxytestosterone

Base Information

• Chemical Name: 11alpha-Hydroxytestosterone
• CAS No.: 3066-12-4
• Molecular Formula: C19H28 O3
• Molecular Weight: 304.43
• UNII: LFI38P8752
• Nikkaji Number: J337.157C
• Wikidata: Q27148945
• Mol file: 3066-12-4.mol

Synonyms:11alpha-Hydroxytestosterone;3066-12-4;11alpha,17beta-Dihydroxyandrost-4-en-3-one;LFI38P8752;NSC-34535;11.alpha.-Hydroxytestosterone;UNII-LFI38P8752;11-alpha,17-beta-Dihydroxyandrost-4-en-3-one;11-Hydroxytestosterone, 11alpha-;11alpha-Hydroxytestosterone, (+)-;delta4-Androsten-3-one-11alpha,17beta-diol;(8S,9S,10R,11R,13S,14S,17S)-11,17-dihydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one;Androst-4-en-3-one, 11,17-dihydroxy-, (11alpha,17beta)-;11,17-dihydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one;SCHEMBL3362406;BDBM91721;CHEBI:79808;11alpha-Hydroxytestosterone, 10;PD019871;11-HYDROXYTESTOSTERONE, 11.ALPHA.-;11.ALPHA.-HYDROXYTESTOSTERONE, (+)-;11.alpha.,17.beta.-Dihydroxy-androst-4-en-3-one;Q27148945;11.ALPHA.,17.BETA.-DIHYDROXYANDROST-4-EN-3-ONE;.DELTA.4-ANDROSTEN-3-ONE-11.ALPHA.,17.BETA.-DIOL;ANDROST-4-EN-3-ONE, 11,17-DIHYDROXY-, (11.ALPHA.,17.BETA.)-

Chemical Property of 11alpha-Hydroxytestosterone

Chemical Property:

• Vapor Pressure: 4.56E-11mmHg at 25°C
• Boiling Point: 476.2°Cat760mmHg
• Flash Point: 255.9°C
• PSA: 57.53000
• Density: 1.19g/cm³
• LogP: 2.85000
• 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%min ^*data from raw suppliers

11α-hydroxy Testosterone ≥97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(=O)C=C1CCC3C2C(CC4(C3CCC4O)C)O
• Isomeric SMILES: C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2[C@@H](C[C@]4([C@H]3CC[C@@H]4O)C)O
• Description: 11α-hydroxy Testosterone is a metabolite of testosterone, produced by the cytochrome P450 (CYP) isoform CYP3A. It can also be generated from testosterone by a mutant of CYP107A1 and from 11α-hydroxy progesterone by the fungus B. bassiana. The biological activity of this metabolite has not been elucidated.

Technology Process of 11alpha-Hydroxytestosterone

There total 12 articles about 11alpha-Hydroxytestosterone 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: 8.0%

Androstenedione (63-05-8) → 11α,17β-dihydroxyandrost-4-ene-3-one (3066-12-4) + 11α-hydroxyandrost-4-ene-3,17-dione (564-33-0)

Guidance literature:

With phosphate buffer; Beauveria sp. culture; at 28 ℃; for 24h;

DOI:10.1007/BF00758431

Reference yield: 1.6%

11-alpha-hydroxyprogesterone (80-75-1,22847-91-2) → 11α,17β-dihydroxyandrost-4-ene-3-one (3066-12-4) + 11α,15α-dihydroxypregn-4-ene-3,20-dione (640-33-5)

Guidance literature:

With Candida albicans; In acetone; for 336h;

DOI:10.1515/znb-2007-0419

Reference yield:

Progesterone (57-83-0) → 6β,11α-dihydroxyprogesterone (600-48-6) + 11α,17β-dihydroxy-5β-androstan-3-one (32693-31-5) + 11-alpha-hydroxyprogesterone (80-75-1,22847-91-2) + 11α,17β-dihydroxyandrost-4-ene-3-one (3066-12-4)

Guidance literature:

With Beauveria bassiana; In acetone;

DOI:10.1016/j.bbalip.2011.01.005

upstream raw materials:

Androstenedione

11-alpha-hydroxyprogesterone

Progesterone

5-androstenediol

Downstream raw materials:

(5α)-androst-9(11)-ene-3,17-dione

5α-androstane-3,11,17-trione

11α,17β-dihydroxy-5α-androstan-3-one

3β,11α,17β-trihydroxy-5α-androstane

Refernces

• 1、 Peart, Patrice C.,Reynolds, William F.,Reese, Paul B.. "The generation of a steroid library using filamentous fungi immobilized in calcium alginate Dedicated to the memory of Professor Sir John W. Cornforth, University of Sussex (1917-2013).". . p. 16 - 24. Retrieved 2016/01/25.
• 2、 Choudhary, Muhammad Iqbal,Nasir, Muhammad,Khan, Shamsun N.,Atif, Muhammad,Ali, Rahat A.,Khalil, Syed M.,Atta-ur-Rahman. "Microbial hydroxylation of hydroxyprogesterones and α-glucosidase inhibition activity of their metabolites". . p. 593 - 599. Retrieved 2007/10/03.