17beta-Hydroxyestra-4,9-dien-3-one

Base Information

• Chemical Name: 17beta-Hydroxyestra-4,9-dien-3-one
• CAS No.: 6218-29-7
• Molecular Formula: C18H24O2
• Molecular Weight: 272.387
• European Community (EC) Number: 612-953-5
• UNII: ZX4VV1AKUF
• ChEMBL ID: CHEMBL2311179
• DSSTox Substance ID: DTXSID80471835
• Nikkaji Number: J629.653J
• Wikipedia: Dienolone
• Mol file: 6218-29-7.mol

Synonyms:6218-29-7;9,10-Dehydro-19-nortestosterone;ZX4VV1AKUF;17beta-Hydroxyestra-4,9-dien-3-one;UNII-ZX4VV1AKUF;RU-3118;CHEMBL2311179;3-Oxo-4,9-estradien-17beta-ol;4,9-Estradien-17beta-ol-3-one;Estra-4,9-diene-17beta-ol-3-one;17 beta-Hydroxy-4,9-estradien-3-one;17-hydroxy-13-methyl-2,6,7,8,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-one;(8S,13S,14S,17S)-17-hydroxy-13-methyl-2,6,7,8,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-one;SCHEMBL3867182;DTXSID80471835;BDBM50422635;17-|A-Hydroxyestra-4,9-dien-3-one;9 pound not10-Dehydro-19-nortestosterone;(17beta)-17-Hydroxyestra-4,9-dien-3-one;17beta-hydroxy-estra-4,9(10)-dien-3-one;3-OXO-4,9-ESTRADIEN-17.BETA.-OL;4,9-ESTRADIEN-17.BETA.-OL-3-ONE;CS-0212818;D4162;EC 612-953-5;ESTRA-4,9-DIENE-17.BETA.-OL-3-ONE;17.BETA.-HYDROXYESTRA-4,9-DIEN-3-ONE;Estra-4,9-dien-3-one, 17-hydroxy-, (17beta)-;Q27295932;(17.BETA.)-17-HYDROXYESTRA-4,9-DIEN-3-ONE;ESTRA-4,9-DIEN-3-ONE, 17-HYDROXY-, (17.BETA.)-

Chemical Property of 17beta-Hydroxyestra-4,9-dien-3-one

Chemical Property:

• Melting Point: 190°C(lit.)
• Refractive Index: 1.585
• Boiling Point: 466.823 °C at 760 mmHg
• PKA: 15.00±0.40(Predicted)
• Flash Point: 198.572 °C
• PSA: 37.30000
• Density: 1.17g/cm³
• LogP: 3.16320
• Solubility.: soluble in Methanol
• Water Solubility.: 53mg/L at 20℃
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 272.177630004
• Heavy Atom Count: 20
• Complexity: 528

Purity/Quality:

99% ^*data from raw suppliers

9(10)-Dehydronandrolone >97.0%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3=C4CCC(=O)C=C4CCC3C1CCC2O
• Isomeric SMILES: C[C@]12CCC3=C4CCC(=O)C=C4CC[C@H]3[C@@H]1CC[C@@H]2O
• Uses: Gestagenic Testosterone (T155000) derivative. A steroid ligand for the cytosol androgen receptor (AR) of rat prostate.

Technology Process of 17beta-Hydroxyestra-4,9-dien-3-one

There total 29 articles about 17beta-Hydroxyestra-4,9-dien-3-one 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: 87.0%

4,9-Androstadiene-3,17-dione (5173-46-6) → 17β-hydroxyestra-4,9-dien-3-one (6218-29-7)

Guidance literature:

With methanol; sodium tetrahydroborate; In dichloromethane; at -78 ℃; for 5h;

DOI:10.1016/j.steroids.2014.09.006

Reference yield: 84.0%

17β-hydroxy-estr-5(10)-en-3-one (1089-78-7) → 17β-hydroxyestra-4,9-dien-3-one (6218-29-7)

Guidance literature:

With polyvinyl pyridine; polyvinylpyridiniumbromide-perbromide; In chloroform; for 20h; Ambient temperature;

Reference yield:

C24H38O2Si → 17β-hydroxyestra-4,9-dien-3-one (6218-29-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 0.5h;

upstream raw materials:

17β-hydroxy-estr-5(10)-en-3-one

(8S,13S,14S,17S)-13-methyl-1,2,4,6,7,8,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolan]-17-ol

acetic acid

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

Downstream raw materials:

(1S,3aS,4S,7aS)-4-[2-(2,5-Dihydroxy-phenyl)-ethyl]-1-hydroxy-7a-methyl-octahydro-inden-5-one

1,4,17β-Tribenzoyloxy-1,3,5(10),9(11)-estratetraen

9⁽¹¹⁾-Dehydroestradiol

17β-benzoyloxy-3,3-ethylenedioxy-5β,10β-oxidoestr-9(11)-ene

Refernces

• 1、 Liu, Yuanyuan,Wang, Yu,Chen, Xi,Wu, Qiaqing,Wang, Min,Zhu, Dunming,Ma, Yanhe. "Regio- and stereoselective reduction of 17-oxosteroids to 17β-hydroxysteroids by a yeast strain Zygowilliopsis sp. WY7905". . p. 17 - 24. Retrieved 2016/12/22.
• 2、 Muddana, Smita S.,Price, Aimee M.,MacBride, Megan M.,Peterson, Blake R.. "11β-alkyl-Δ9-19-nortestosterone derivatives: High-affinity ligands and potent partial agonists of the androgen receptor". . p. 4985 - 4988. Retrieved 2007/10/03.