11beta-Hydroxyandrostenedione

Base Information

• Chemical Name: 11beta-Hydroxyandrostenedione
• CAS No.: 382-44-5
• Molecular Formula: C19H26O3
• Molecular Weight: 302.414
• NSC Number: 17102,12167
• UNII: 41G81C896T
• DSSTox Substance ID: DTXSID8040931
• Nikkaji Number: J104.102I
• Wikipedia: 11%CE%B2-Hydroxyandrostenedione
• Wikidata: Q27103427
• Metabolomics Workbench ID: 35347
• ChEMBL ID: CHEMBL2311170
• Mol file: 382-44-5.mol

Synonyms:382-44-5;11beta-Hydroxyandrostenedione;4-Androsten-11beta-ol-3,17-dione;11-beta-hydroxyandrostenedione;11beta-Hydroxyandrost-4-ene-3,17-dione;NSC-17102;U 2826;11beta-Hydroxy-4-androstene-3,17-dione;Androst-4-ene-3,17-dione-11beta-ol;11b-Hydroxy-androst-4-ene-3,17-dione;11beta-Hydroxy-4-androsten-3,17-dione;11.beta.-Hydroxy-4-androsten-3,17-dione;UNII-41G81C896T;CHEBI:27967;Androst-4-ene-3,17-dione, 11-hydroxy-, (11b)-;NSC 12167;NSC-12167;41G81C896T;(8S,9S,10R,11S,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;4-Androstene-11.beta.-ol-3,17-dione;Androst-4-ene-3,17-dione, 11.beta.-hydroxy-;Androst-4-ene-3,17-dione, 11-hydroxy-, (11.beta.)-;564-33-0;Androst-4-ene-3, 11.beta.-hydroxy-;(8S,9S,10R,11S,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;Androst-4-ene-3, 11-hydroxy-, (11.beta.)-;11-Hydroxyandrost-4-ene-3,17-dione;4-Androsten-11|A-ol-3,17-dione;Androst-4-ene-3,17-dione, 11beta-hydroxy-;(8S,9S,10R,11S,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;SCHEMBL618699;NPC-01;CHEMBL2311170;DTXSID8040931;4-Androsten-11-ol-3,17-dione;4-Androsten-11b-ol-3,17-dione;NSC12167;NSC17102;LMST02020066;AKOS027380941;11.BETA.-HYDROXYANDROSTENEDIONE;CS-W012117;11-hydroxy-androst-4-ene-3,17-dione;NCGC00485120-01;11-Hydroxyandrost-4-ene-3,17-dione #;AS-62675;11beta-hydroxy-androst-4-ene-3,17-dione;HY-114464;Androst-4-en-3,17-dione, 11beta-hydroxy-;4-ANDROSTEN-11.BETA.-OL-3,17-DIONE;C05284;F85616;U-2826;11.BETA.-HYDROXYANDROST-4-ENE-3,17-DIONE;.DELTA.4-ANDROSTEN-11.BETA.-OL-3,17-DIONE;.DELTA.4-ANDROSTENE-11.BETA.-OL-3,17-DIONE;Androst-4-ene-3,17-dione, 11beta-hydroxy- (8CI);Q27103427;AFE01EF4-A83C-40B0-A091-06E714D55FB9;Androst-4-ene-3,17-dione, 11-hydroxy-, (11beta)-;(11.BETA.)-11-HYDROXYANDROST-4-ENE-3,17-DIONE;11.BETA.-HYDROXY-.DELTA.4-ANDROSTENE-3,17-DIONE

Chemical Property of 11beta-Hydroxyandrostenedione

Chemical Property:

• Vapor Pressure: 4.95E-11mmHg at 25°C
• Melting Point: 197-199℃
• Refractive Index: 1.569
• Boiling Point: 475.3 °C at 760 mmHg
• 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:

98%,99%, ^*data from raw suppliers

4-Androsten-11β-ol-3,17-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
• Recent ClinicalTrials: Efficacy and Safety Study of NPC-01 to Treat Dysmenorrhea
• Uses: 4-Androsten-11β-ol-3,17-dione is a steroid hormone. An analog of Androstenedione (A637550).

Technology Process of 11beta-Hydroxyandrostenedione

There total 17 articles about 11beta-Hydroxyandrostenedione 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: 69.4%

Androstenedione (63-05-8) → (8S,9S,10R,11S,13S,14S)-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 (382-44-5) + 14-hydroxy-4-androstene-3,17-dione (564-63-6) + 14alpha-Hydroxytestosterone (4075-20-1)

Guidance literature:

With D-glucose; mycelium of Curvularia lunata fungus; In water; for 72h;

DOI:10.1023/A:1011925608119

Reference yield: 38.1%

Androstenedione (63-05-8) → (8S,9S,10R,11S,13S,14S)-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 (382-44-5) + 6α-hydroxy-androst-4-ene-3,17-dione (24704-84-5) + 11α-hydroxyandrost-4-ene-3,17-dione (564-33-0)

Guidance literature:

With phosphate buffer; D-glucose; tieghemella orchidis; calcium chloride; In methanol; at 28 ℃; for 24h; Product distribution; other derivatives of androstene, other microbiological reagents, var reactions;

DOI:10.1007/BF00758303

Reference yield: 24.0%

HYDROCORTISONE (50-23-7) → (8S,9S,10R,11S,13S,14S)-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 (382-44-5) + cortienic acid (3597-45-3)

Guidance literature:

With potassium hydroxide; In ethanol; for 1.66667h; Mechanism; Ambient temperature; in presence and absence of O₂, further reagent: NaOMe;

DOI:10.1016/S0039-128X(81)90264-6

upstream raw materials:

HYDROCORTISONE

Androstenedione

hydrocortisone acetate

androstendione

Downstream raw materials:

11β-hydroxytestosterone

androst-4,9⁽¹¹⁾-dien-3,17-dione

Benzoic acid (8S,9S,10R,11S,13S,14S)-10,13-dimethyl-3,17-dioxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-11-yl ester

11β-(p-hydroxyphenylacetoxy)-4-androstene-3,17-dione

Refernces

• 1、 Devendran, Saravanan,Mythen, Sean M.,Ridlon, Jason M.. "The desA and desB genes from Clostridium scindens ATCC 35704 encode steroid-17,20-desmolase". . p. 1005 - 1014. Retrieved 2018/06/22.
• 2、 Yazdi, Mojtaba Tabatabaei,Arabi, Homeira,Faramarzi, Mohammad Ali,Ghasemi, Younes,Amini, Mohsen,Shokravi, Shadman,Mohseni, Farzaneh Aziz. "Biotransformation of hydrocortisone by a natural isolate of Nostoc muscorum". . p. 2205 - 2209. Retrieved 2007/10/03.