11-Ketotestosterone

Base Information

• Chemical Name: 11-Ketotestosterone
• CAS No.: 564-35-2
• Deprecated CAS: 1050679-19-0
• Molecular Formula: C19H26O3
• Molecular Weight: 302.414
• UNII: KF38W1A85U
• DSSTox Substance ID: DTXSID8036499,DTXSID20859491
• Nikkaji Number: J381.141G
• Wikipedia: 11-Ketotestosterone
• Wikidata: Q4547229
• Metabolomics Workbench ID: 70598
• Mol file: 564-35-2.mol

Synonyms:11-ketotestosterone;11-ketotestosterone, (17beta)-isomer;11-oxotestosterone;17 beta-hydroxyandrost-4-ene-3,11-dione

Chemical Property of 11-Ketotestosterone

Chemical Property:

• Vapor Pressure: 4.3E-11mmHg at 25°C
• Melting Point: 183-184 °C(Solv: acetone (67-64-1); hexane (110-54-3))
• Refractive Index: 1.569
• Boiling Point: 476.791 °C at 760 mmHg
• PKA: 14.79±0.60(Predicted)
• Flash Point: 256.265 °C
• PSA: 54.37000
• Density: 1.191 g/cm³
• LogP: 3.05820
• XLogP3: 2
• 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

11-Keto testosterone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC12CCC(=O)C=C1CCC3C2C(=O)CC4(C3CCC4O)C
• Isomeric SMILES: C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2C(=O)C[C@]4([C@H]3CC[C@@H]4O)C
• Description: 11-keto Testosterone (CRM) (Item No. 9002654) is a certified reference material that is structurally categorized as an androgen. It is a significant hormone in certain fish, regulating the development of sexual development and behavior. 11-keto Testosterone binds the stickleback kidney androgen receptor (EC50 = 43 nM). 11-keto Testosterone, at 10 nM, significantly activates the human androgen receptor expressed in zebrafish liver cells. This product is intended for research and forensic applications.
• Uses: A metabolite of Adrenosterone.

Technology Process of 11-Ketotestosterone

There total 32 articles about 11-Ketotestosterone 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: 67.0%

adrenosterone (382-45-6) → 11-ketotestosterone (564-35-2)

Guidance literature:

With sodium tetrahydroborate; In pyridine; methanol;

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

Reference yield: 65.0%

(+/-)-(2,3β,3aβ,5aα,8,9,9aβ,9bα)-octahydro-3-tert-butyldimethylsilyloxy-6α-<3'-chlorobut-2'(E)-en-1'-yl>-3a,6β-dimethyl-1H-benzindene-5,7(4H,6H)-dione (87530-50-5,101833-74-3) → (+/-)-11-ketotestosterone (564-35-2,53187-98-7,87583-72-0)

Guidance literature:

With formic acid; perchloric acid; Heating;

DOI:10.1016/S0040-4039(00)88118-6

Reference yield: 49.0%

(8S,9S,10R,13S,14S,17S)-10,13-Dimethyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,11,17-triol (81176-76-3) → adrenosterone (382-45-6) + 11-ketotestosterone (564-35-2)

Guidance literature:

With 4-(N,N-dimethylamino)pyridinium chlorochromate; In dichloromethane; for 4h;

DOI:10.1021/jo00348a045

upstream raw materials:

adrenosterone

11-keto-5β-dihydrotestosterone

17β-propionyloxy-androst-4-ene-3,11-dione

17-acetoxyandrost-4-ene-3,11-dione

Downstream raw materials:

3α,17β-dihydroxy-5β-androstan-11-one

11-ketoetiocholanolone

11-ketodihydrotestosterone

(+/-)-adrenosterone

Refernces

• 1、 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 2007/10/03.
• 2、 Royen, Luc A. Van,Mijngheer, Roelant,Clercq, Pierre J. De. "INTRAMOLECULAR DIELS-ALDER REACTION WITH FURAN-DIENE. TOTAL SYNTHESIS OF (+/-)-11-KETOTESTOSTERONE AND (+/-)-ADRENOSTERONE.". . p. 4667 - 4680. Retrieved 2007/10/02.