11b-Hydroxyandrost-4-ene-3,17-dione

Base Information

• Chemical Name: 11b-Hydroxyandrost-4-ene-3,17-dione
• CAS No.: 564-33-0
• Molecular Formula: C19H26O3
• Molecular Weight: 302.41
• UNII: AX0E3RB33W
• DSSTox Substance ID: DTXSID801019361
• Nikkaji Number: J337.166B
• Wikidata: Q27274166
• Mol file: 564-33-0.mol

Synonyms:564-33-0;11b-Hydroxyandrost-4-ene-3,17-dione;UNII-AX0E3RB33W;AX0E3RB33W;11alpha-Hydroxyandrostendione;11alpha-Hydroxyandrostenedione;(8S,9S,10R,11R,13S,14S)-11-Hydroxy-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17(2H,6H)-dione;NSC 9720;11alpha-Hydroxy-4-androsten-3,17-dione;(8S,9S,10R,11R,13S,14S)-11-hydroxy-10,13-dimethyl-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-3H-cyclopenta[a]phenanthrene-3,17(2H)-dione;NSC-9720;11alpha-hydroxyandrost-4-ene-3,17-dione;11a-hydroxyandrostenedione;SCHEMBL3360918;CHEBI:190716;DTXSID801019361;11.ALPHA.-HYDROXYANDROSTENDIONE;11.ALPHA.-HYDROXYANDROSTENEDIONE;(8S,9S,10R,11R,13S,14S)-11-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dione;ANDROST-4-EN-11.ALPHA.-OL-3,17-DIONE;11.ALPHA.-HYDROXY-4-ANDROSTEN-3,17-DIONE;11.ALPHA.-HYDROXYANDROST-4-ENE-3,17-DIONE;Q27274166;ANDROST-4-ENE-3,17-DIONE, 11.ALPHA.-HYDROXY-;ANDROST-4-ENE-3,17-DIONE, 11-HYDROXY-, (11.ALPHA.)-;(3aS,3bS,9aR,9bS,10R,11aS)-10-hydroxy-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthrene-1,7-dione;(8S,10R,11R,13S)-11-Hydroxy-10,13-dimethyl-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-2H-cyclopenta[a]phenanthrene-3,17-dione

Chemical Property of 11b-Hydroxyandrost-4-ene-3,17-dione

Chemical Property:

• Vapor Pressure: 4.95E-11mmHg at 25°C
• Melting Point: 226-227 °C
• Refractive Index: 1.569
• Boiling Point: 475.3 °C at 760 mmHg
• PKA: 14.49±0.60(Predicted)
• Flash Point: 255.4 °C
• PSA: 54.37000
• Density: 1.19 g/cm³
• LogP: 3.05820
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 302.18819469
• Heavy Atom Count: 22
• Complexity: 577

Purity/Quality:

99.0% Min ^*data from raw suppliers

(8S,9S,10R,11R,13S,14S)-11-Hydroxy-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17(2H,6H)-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(=O)C=C1CCC3C2C(CC4(C3CCC4=O)C)O
• Isomeric SMILES: C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2[C@@H](C[C@]4([C@H]3CCC4=O)C)O

Technology Process of 11b-Hydroxyandrost-4-ene-3,17-dione

There total 30 articles about 11b-Hydroxyandrost-4-ene-3,17-dione 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: 98.0%

Androstenedione (63-05-8) → 11α-hydroxyandrost-4-ene-3,17-dione (564-33-0)

Guidance literature:

With Gelasinospora retispora GRK₀₀₂; In methanol; water; at 34 ℃; for 144h; pH=5; Microbiological reaction;

DOI:10.1016/j.molcatb.2010.07.008

Reference yield: 61.7%

Androstenedione (63-05-8) → 5α-androst-3,6,17-trione (2243-05-2) + 11α-hydroxyandrost-4-ene-3,17-dione (564-33-0) + 7α-hydroxyandrost-4-ene-3,17-dione (62-84-0,31427-20-0) + 6β-hydroxy-4-androstene-3,17-dione (63-00-3)

Guidance literature:

With water; In N,N-dimethyl-formamide; at 28 ℃; Rhizopus nigricans;

DOI:10.1007/BF00765613

Reference yield: 46.0%

Epicortisol (566-35-8) → 11α-hydroxyandrost-4-ene-3,17-dione (564-33-0)

Guidance literature:

With manganese(IV) oxide;

DOI:10.1016/0039-128X(94)90027-2

upstream raw materials:

androstendione

Androstenedione

3,3:17,17-bis(ethylenedioxy)androst-5-en-11α-ol

Epicortisol

Downstream raw materials:

3-ethoxyandrosta-3,5-dien-17-one

11β-hydroxy-16α,17α-epoxyprogesterone

Refernces

• 1、 Kolet, Swati P.,Niloferjahan, Siddiqui,Haldar, Saikat,Gonnade, Rajesh,Thulasiram, Hirekodathakallu V.. "Biocatalyst mediated production of 6β,11α-dihydroxy derivatives of 4-ene-3-one steroids". . p. 1152 - 1158. Retrieved 2013/10/08.
• 2、 Koshimura, Masahiro,Utsukihara, Takamitsu,Hara, Asako,Mizobuchi, Syuhei,Horiuchi, C. Akira,Kuniyoshi, Masayuki. "Hydroxylation of steroid compounds by Gelasinospora retispora". experimental part. p. 72 - 77. Retrieved 2010/12/20.