7-Keto-dehydroepiandrosterone

Base Information

• Chemical Name: 7-Keto-dehydroepiandrosterone
• CAS No.: 566-19-8
• Molecular Formula: C19H26O3
• Molecular Weight: 302.414
• Hs Code.: 2937290090
• UNII: 2334LJD2E9
• DSSTox Substance ID: DTXSID801024029
• Nikkaji Number: J672.472H
• Wikipedia: 7-Keto-DHEA
• Wikidata: Q4642869
• Metabolomics Workbench ID: 155660
• Mol file: 566-19-8.mol

Synonyms:7-keto-DHEA;7-ketodehydroepiandrosterone;7-oxo-dehydroepiandrosterone;7-oxodehydroepiandrosterone

Chemical Property of 7-Keto-dehydroepiandrosterone

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 4.15E-11mmHg at 25°C
• Melting Point: 240.0-244.0oC
• Refractive Index: 1.569
• Boiling Point: 477.1 °C at 760 mmHg
• PKA: 14.67±0.60(Predicted)
• Flash Point: 256.5 °C
• PSA: 54.37000
• Density: 1.19 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:

99.9% ^*data from raw suppliers

(3S,8R,9S,10R,13S,14S)-3-Hydroxy-10,13-dimethyl-3,4,9,10,11,12,13,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-7,17(2H,8H)-dione 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2=O)C(=O)C=C4C3(CCC(C4)O)C
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)C(=O)C=C4[C@@]3(CC[C@@H](C4)O)C
• Recent ClinicalTrials: A Study to Investigate the Effect of 7-Keto on Resting Metabolic Rate in Overweight Adults

Technology Process of 7-Keto-dehydroepiandrosterone

There total 21 articles about 7-Keto-dehydroepiandrosterone 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: 81.1%

dehydroepiandrosterone (53-43-0) → 5-androstene-3β-ol-7,17-dione (566-19-8)

Guidance literature:

With tert.-butylhydroperoxide; N-hydroxyphthalimide; cobalt(II) acetate; In acetone; at 20 ℃; for 5h; regioselective reaction;

DOI:10.1016/j.steroids.2014.12.004

Reference yield: 65.0%

(3S,8R,9S,10R,13S,14S)-3-hydroxy-10,13-dimethyl-1,3,4,8,9,10,11,12,13,14,15,16-dodecahydrospiro[cyclopenta[a]phenanthrene-17,2'-[1,3]dioxolan]-7(2H)-one (166173-97-3) → 5-androstene-3β-ol-7,17-dione (566-19-8)

Guidance literature:

With perchloric acid; water; In acetone; at 20 ℃; for 20h;

Reference yield: 65.0%

dehydroepiandrosterone (53-43-0,571-35-7,2283-82-1,24357-33-3,25375-38-6,102340-20-5) → 3β-hydroxyandrost-5-ene-7,17-dione (566-19-8)

Guidance literature:

With tert.-butylhydroperoxide; sodium chlorite; In water; acetonitrile; at 50 ℃; for 20h;

DOI:10.1016/j.tet.2007.01.012

upstream raw materials:

dehydroepiandrosterone

dehydroepiandrosterone

prasterone acetate

di-tert-butyl chromate

Downstream raw materials:

androsta-3,5-diene-7,17-dione

3beta,17beta-Dihydroxyandrost-5-en-7-one

Androst-5-ene-3beta,7alpha,17beta-triol

5-androstene-3β,7β,17β-triol

Refernces

• 1、 Yildirim, Kudret,Kuru, Ali,Y?lmazer Keskin, Semra,Ergin, Sinan. "Microbial transformation of dehydroepiandrosterone (DHEA) by some fungi". . p. 465 - 474. Retrieved 2020/11/12.
• 2、 Horn, Evan J.,Rosen, Brandon R.,Chen, Yong,Tang, Jiaze,Chen, Ke,Eastgate, Martin D.,Baran, Phil S.. "Scalable and sustainable electrochemical allylic C-H oxidation". . p. 77 - 81. Retrieved 2016/06/01.