Prenortestosterone

Base Information

• Chemical Name: Prenortestosterone
• CAS No.: 1089-78-7
• Molecular Formula: C18H26 O2
• Molecular Weight: 274.403
• European Community (EC) Number: 600-891-1
• NSC Number: 37320
• UNII: 99T8YP2W04
• DSSTox Substance ID: DTXSID90148768
• Nikkaji Number: J554.834I
• Wikidata: Q27148891
• Mol file: 1089-78-7.mol

Synonyms:Prenortestosterone;17-Hydroxy-estr-5(10)-en-3-one;1089-78-7;Estr-5(10)-en-3-one, 17.beta.-hydroxy-;UNII-99T8YP2W04;99T8YP2W04;NSC-37320;17beta-Hydroxyestr-5(10)-en-3-one;(8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-2,4,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-one;Estr-5(10)-en-3-one, 17-hydroxy-, (17.beta.)-;Isonandrolone;NSC 37320;SCHEMBL3451745;CHEBI:79759;DTXSID90148768;NSC37320;17-Hydroxyestr-5(10)-en-3-one #;17beta-hydroxyoestr-5(10)-en-3-one;Androst-5(10)-en-17.beta.-ol-3-one;Estr-5(10)-en-3-one, (17.beta.)-;Delta(5,10)-dehydro-19-nordihydrotestosterone;ESTR-5(10)-EN-17.BETA.-OL-3-ONE;17.BETA.-HYDROXYESTR-5(10)-EN-3-ONE;Estr-5(10)-en-17-ol-3-one, (17.beta.)-;Q27148891;17.BETA.-HYDROXY-19-NORANDROST-5(10)-EN-3-ONE

Chemical Property of Prenortestosterone

Chemical Property:

• Vapor Pressure: 3.79E-09mmHg at 25°C
• Melting Point: 199.8-201 °C (decomp)(Solv: ethyl acetate (141-78-6))
• Boiling Point: 428.7°C at 760 mmHg
• PKA: 15.06±0.40(Predicted)
• Flash Point: 182.9°C
• PSA: 37.30000
• Density: 1.14g/cm³
• LogP: 3.63320
• Water Solubility.: 3.1mg/L at 20℃
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 274.193280068
• Heavy Atom Count: 20
• Complexity: 478

Purity/Quality:

99.9% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2O)CCC4=C3CCC(=O)C4
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C3CCC(=O)C4
• Uses: Testosterone (T155000) derivative. Inhibits estrogen biosynthesis. A steroid ligand for the cytosol androgen receptor (AR) of rat prostate.

Technology Process of Prenortestosterone

There total 16 articles about Prenortestosterone 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: 11.0%

19-oxoandrostenedione (968-49-0) → 17β-hydroxy-estr-5(10)-en-3-one (1089-78-7) + estra-5(10)-en-3,17-dione (3962-66-1) + (19R)-19-hydroxy-5β,19-cycloandrostane-3,17-dione (160617-57-2) + (19R)-17β,19-dihydroxy-5β,19-cycloandrostan-3-one (192373-63-0)

Guidance literature:

With ammonia; lithium; In tetrahydrofuran; for 0.5h;

DOI:10.1039/a604405k

Reference yield:

3-methoxy-17-hydroxyestra-2,5(10)-diene (1091-93-6) → 17β-hydroxy-estr-5(10)-en-3-one (1089-78-7)

Guidance literature:

With oxalic acid;

DOI:10.1021/ja01117a064

Reference yield:

3-O-methyl-17β-oestradiol (1035-77-4) + isopropyl alcohol (67-63-0,8013-70-5) → 17β-hydroxy-estr-5(10)-en-3-one (1089-78-7)

Guidance literature:

In tetrahydrofuran; methanol; water;

upstream raw materials:

3-methoxy-17-hydroxyestra-2,5⁽¹⁰⁾-diene

3-((Ξ)-2.3-dihydroxy-propyloxy)-estratrien-(1.3.5(10))-ol-(17β)

19-oxoandrostenedione

estradiol

Downstream raw materials:

3-Oxo-17β-acetoxy-Δ⁵⁽¹⁰⁾-oestren

10α-Methyl-17β-acetoxy-A-nor-5α-oestran-3-on

3,3-(ethylenedioxy)-5(10)-estren-17β-yl acetate

17β-hydroxy-10β-mercaptoestr-4-en-3-one

Refernces

• 1、 Cheng, Qian,Sohl, Christal D.,Yoshimoto, Francis K.,Guengerich, F. Peter. "Oxidation of dihydrotestosterone by human cytochromes P450 19A1 and 3A4". . p. 29554 - 29567. Retrieved 2013/01/14.
• 2、 Templeton, John F.,Ling, Yangzhi,Lin, Weiyang,Majgier-Baranowska, Helena,Marat, Kirk. "19-hydroxy-5β,19-cyclosteroids: Synthesis, isomerization and ring opening". . p. 1895 - 1904. Retrieved 2007/10/03.