Adrenosterone

Base Information

• Chemical Name: Adrenosterone
• CAS No.: 382-45-6
• Deprecated CAS: 293738-14-4
• Molecular Formula: C19H24O3
• Molecular Weight: 306.445
• Hs Code.: 2942000000
• European Community (EC) Number: 206-843-2
• NSC Number: 12166
• UNII: AE4E9102GY
• DSSTox Substance ID: DTXSID301020915,DTXSID801019311
• Nikkaji Number: J5.714B
• Wikipedia: Adrenosterone
• Wikidata: Q4684756
• Metabolomics Workbench ID: 39031
• ChEMBL ID: CHEMBL485683
• Mol file: 382-45-6.mol

Synonyms:(+)-Adrenosterone;11-Keto-4-androstene-3,17-dione;11-Oxo-4-androstene-3,17-dione;Andrenosterone;NSC 12166;Reichstein's substance G;(8S,9S,10R,13S,14S)-10,13-Dimethyl-6,7,8,9,10,12,13,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,11,17(2H)-trione;Androst-4-ene-3,11,17-trione;

Chemical Property of Adrenosterone

Chemical Property:

• Appearance/Colour: Off-White to Pale Yellow Solid
• Vapor Pressure: 3.14E-09mmHg at 25°C
• Melting Point: 219-222 °C(lit.)
• Refractive Index: 290 ° (C=0.2, EtOH)
• Boiling Point: 476.078 °C at 760 mmHg
• Flash Point: 205.986 °C
• PSA: 51.21000
• Density: 1.188 g/cm³
• LogP: 3.26640
• Storage Temp.: Refrigerator
• Water Solubility.: 98.49mg/L(23.5 oC)
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 300.17254462
• Heavy Atom Count: 22
• Complexity: 616

Purity/Quality:

99% ^*data from raw suppliers

Adrenosterone >98.0%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC12CCC(=O)C=C1CCC3C2C(=O)CC4(C3CCC4=O)C
• Isomeric SMILES: C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2C(=O)C[C@]4([C@H]3CCC4=O)C
• Recent ClinicalTrials: Dissecting the IMpact of 11-OXygenated and Classic Androgens on Skeletal Muscle Insulin Sensitivity (DIMOXIS)
• Uses: Androgenic activity;Androgenic steroid Steroid hormone with weak androgenic effects.

Technology Process of Adrenosterone

There total 118 articles about Adrenosterone 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%

Cortisone (53-06-5) → adrenosterone (382-45-6)

Guidance literature:

In water; acetonitrile; at 20 ℃; Electrochemical reaction;

DOI:10.1002/chem.202100446

Reference yield: 98.0%

(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) → adrenosterone (382-45-6)

Guidance literature:

With Jones's reagent; In acetone; at 20 ℃; for 0.0833333h;

DOI:10.1135/cccc19842932

Reference yield: 91.0%

HYDROCORTISONE (50-23-7) → adrenosterone (382-45-6)

Guidance literature:

With dipyridinium dichromate; In dichloromethane; for 44h; Ambient temperature;

DOI:10.1016/S0039-128X(97)00052-4

upstream raw materials:

11-keto-1,4-androstene-3,17-dione

17,21-dihydroxy-pregn-4-ene-3,11,20-trione

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

cortienic acid

Downstream raw materials:

5β-Androstan-3,11,17-trion

(8S,9S,10R,13S,14S)-10,13-Dimethyl-3-(2-nitro-phenyldisulfanyl)-2,7,8,9,10,12,13,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-11,17-dione

(8S,9S,10R,13S,14S)-10,13-Dimethyl-3-phenyldisulfanyl-2,7,8,9,10,12,13,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-11,17-dione

(8S,9S,10R,13S,14S)-10,13-Dimethyl-3-(2-nitro-phenyldisulfanyl)-6-(2-nitro-phenylsulfanyl)-2,7,8,9,10,12,13,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-11,17-dione

Refernces

• 1、 Acosta, C. Kirk,Rao, Pemmaraju N.,Kim, Hyun K.. "Tetrapropylammonium perruthenate as a mild and efficient oxidant for sensitive steroidal alcohols". . p. 205 - 208. Retrieved 1993.
• 2、 Ullrich, René,Poraj-Kobielska, Marzena,Scholze, Steffi,Halbout, Claire,Sandvoss, Martin,Pecyna, Marek J.,Scheibner, Katrin,Hofrichter, Martin. "Side chain removal from corticosteroids by unspecific peroxygenase". . p. 84 - 93. Retrieved 2018.
• 3、 Sommer, Florian,Kappe, C. Oliver,Cantillo, David. "Electrochemically Enabled One-Pot Multistep Synthesis of C19 Androgen Steroids". . p. 6044 - 6049. Retrieved 2021.
• 4、 Lokman, P. Mark,Irwin, Jacob L.,Blackwell, Leonard F.,Davie, Peter S.,Thomas, Mervyn,Young, Graham. "A simple two-step method for the conversion of [3H]cortisol to [3H]- 11-ketotestosterone". . p. 655 - 658. Retrieved 1997.
• 5、 -. "HYDROXYSTEROID COMPOUNDS, THEIR INTERMEDIATES, PROCESS OF PREPARATION, COMPOSITION AND USES THEREOF". . . Retrieved 2016/02/09.