11beta-Hydroxyandrosterone

Base Information

• Chemical Name: 11beta-Hydroxyandrosterone
• CAS No.: 57-61-4
• Molecular Formula: C19H30 O3
• Molecular Weight: 306.445
• UNII: 0JYD539GC3
• DSSTox Substance ID: DTXSID301018932
• Nikkaji Number: J8.599E
• Wikidata: Q27116006
• Metabolomics Workbench ID: 35365
• ChEMBL ID: CHEMBL1908033
• Mol file: 57-61-4.mol

Synonyms:11 beta-hydroxyandrosterone;11 beta-hydroxyandrosterone, (3alpha,5alpha)-isomer;11 beta-hydroxyandrosterone, (3alpha,5alpha,11alpha)-isomer;11 beta-hydroxyandrosterone, (3alpha,5beta)-isomer;11 beta-hydroxyandrosterone, (3alpha,5beta,11alpha)-isomer;11 beta-hydroxyandrosterone, (3alpha,5beta,11beta)-isomer;11 beta-hydroxyandrosterone, (3beta,5alpha,11beta)-isomer;11 beta-hydroxyandrosterone, (3beta,5beta,11beta)-isomer;11 beta-hydroxyetiocholanolone;11-hydroxyetiocholanolone;3alpha,11beta-dihydroxy-5beta-androstan-17-one

Chemical Property of 11beta-Hydroxyandrosterone

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 197-200 °C(Solv: acetone (67-64-1); ethyl ether (60-29-7); ligroine (8032-32-4))
• Boiling Point: 454.7°Cat760mmHg
• PKA: 14.62±0.70(Predicted)
• Flash Point: 242.9°C
• PSA: 57.53000
• Density: 1.158g/cm³
• LogP: 2.92990
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 306.21949481
• Heavy Atom Count: 22
• Complexity: 489

Purity/Quality:

98%min ^*data from raw suppliers

11-β-Hydroxyandrosterone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(CC1CCC3C2C(CC4(C3CCC4=O)C)O)O
• Isomeric SMILES: C[C@]12CC[C@H](C[C@@H]1CC[C@@H]3[C@@H]2[C@H](C[C@]4([C@H]3CCC4=O)C)O)O
• Uses: 11-β-Hydroxyandrosterone is a steroid metabolite of Andosterone (A637535), and is one of the major hormones monitored (in urine) when testing athletes for anabolic steroid usage.

Technology Process of 11beta-Hydroxyandrosterone

There total 24 articles about 11beta-Hydroxyandrosterone 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: 70.0%

2-oxa-2-((3R,5S,8S,9S,10S,11S,13S,14S,17R)-3,11,17-trihydroxy-10,13-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethyl acetate (4004-75-5) → (3R,5S,8S,9S,10S,11S,13S,14S)-3,11-dihydroxy-10,13-dimethyl-tetradecahydro-2H-cyclopenta[a]phenanthren-17(14H)-one (57-61-4)

Guidance literature:

2-oxa-2-((3R,5S,8S,9S,10S,11S,13S,14S,17R)-3,11,17-trihydroxy-10,13-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethyl acetate; With sodium tetrahydroborate; ethanol; In dichloromethane; at 10 - 25 ℃;

With sodium periodate; In methanol; dichloromethane; water; acetone; at 60 ℃;

Reference yield:

cis-androsterone (53-41-8) → 1β,3α-dihydroxy-5α-androstan-17-one (66885-58-3) + 3α,11β-dihydroxy-17a-oxa-D-homo-5α-androstan-17-one (1268707-73-8) + 1β,3α-dihydroxy-17a-oxa-D-homo-5α-androstan-17-one (1268707-72-7) + androstanediol (1852-53-5) + (3R,5S,8S,9S,10S,11S,13S,14S)-3,11-dihydroxy-10,13-dimethyl-tetradecahydro-2H-cyclopenta[a]phenanthren-17(14H)-one (57-61-4) + (4aS,4bR,8R,10bR,12aS)-8-hydroxy-12a-methylhexadecahydro-2H-naphtho[2,1-f]chromen-2-one (4363-08-0)

Guidance literature:

With Aspergillus tamarii KITA; In N,N-dimethyl-formamide; for 120h;

DOI:10.1016/j.jsbmb.2009.12.003

Reference yield:

→ rac-3β,11β-dihydroxy-5α-androstan-17-one (57-61-4,514-17-0,739-26-4,2551-74-8,2618-30-6,3272-49-9,3461-66-3,4299-92-7,7013-18-5,7162-50-7,7801-12-9,25848-75-3,32212-55-8,91547-81-8,108739-34-0,116698-46-5)

Guidance literature:

With potassium tert-butylate; benzene; Erhitzen mit wss.Dioxan auf 220grad und Erwaermen mit wss.-methanol.NaOH;

DOI:10.1021/ja01605a016

upstream raw materials:

11β-hydroxy-3β-(toluene-4-sulfonyloxy)-5α-androstan-17-one

3β,11β-dihydroxy-5α-androstan-17-one

21-acetoxy-3β,17-dihydroxy-5α-pregnane-11,20-dione

cis-androsterone

Downstream raw materials:

5α-androst-2-ene-11,17-dione

5α-androstane-3,11,17-trione

3α,11β-dihydroxy-5α-androstan-17-one-(2,4-dinitro-phenylhydrazone)

Refernces

• 1、 -. "NEUROACTIVE STEROIDS, COMPOSITIONS, AND USES THEREOF". . . Retrieved 2014/01/08.