11alpha-Hydroxycanrenone

Base Information

• Chemical Name: 11alpha-Hydroxycanrenone
• CAS No.: 192569-17-8
• Molecular Formula: C22H28O4
• Molecular Weight: 356.462
• European Community (EC) Number: 606-276-4
• DSSTox Substance ID: DTXSID901315221
• Nikkaji Number: J2.932.728I
• Wikidata: Q76416060
• Mol file: 192569-17-8.mol

Synonyms:11alpha-Hydroxycanrenone;192569-17-8;11-alpha-Hydroxycarvenone;(8S,9S,10R,11R,13S,14S,17R)-11-hydroxy-10,13-dimethylspiro[2,8,9,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthrene-17,5'-oxolane]-2',3-dione;Pregna-4,6-diene-21-carboxylic acid, 11,17-dihydroxy-3-oxo-, gamma-lactone, (11alpha,17alpha)-;11-hydroxy-10,13-dimethylspiro[2,8,9,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthrene-17,5'-oxolane]-2',3-dione;SCHEMBL14085002;DTXSID901315221;AS-73900;(1R,3aS,3bS,9aR,9bS,10R,11aS)-10-hydroxy-9a,11a-dimethyl-2,3,3a,3b,7,8,9,9a,9b,10,11,11a-dodecahydrospiro[cyclopenta[a]phenanthrene-1,2'-oxolane]-5',7-dione

Chemical Property of 11alpha-Hydroxycanrenone

Chemical Property:

• Appearance/Colour: yellow crystalline solid
• Melting Point: 232-234°C
• Refractive Index: 1.598
• Boiling Point: 584.7 °C at 760 mmHg
• PKA: 14.55±0.60(Predicted)
• Flash Point: 207.3 °C
• PSA: 63.60000
• Density: 1.25 g/cm³
• LogP: 3.34090
• Storage Temp.: -20?C Freezer
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 356.19875937
• Heavy Atom Count: 26
• Complexity: 751

Purity/Quality:

99% ^*data from raw suppliers

11-alpha-Hydroxycarvenone 98 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(=O)C=C1C=CC3C2C(CC4(C3CCC45CCC(=O)O5)C)O
• Isomeric SMILES: C[C@]12CCC(=O)C=C1C=C[C@@H]3[C@@H]2[C@@H](C[C@]4([C@H]3CC[C@@]45CCC(=O)O5)C)O
• Uses: 11α-Hydroxy Canrenone is the key intermediate in the synthesis of Eplerenone, a cardiovascular drug. Canrenone was biotransformed into 11α-Hydroxycanrenone by Aspergillus ochraceus SIT34205.

Technology Process of 11alpha-Hydroxycanrenone

There total 3 articles about 11alpha-Hydroxycanrenone 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: 90.0%

canrenone (976-71-6) → 11α-hydroxyl canrenone (192569-17-8)

Guidance literature:

With D-glucose; peptone; In water;

Reference yield:

canrenone (976-71-6) → 11α-hydroxyl canrenone (192569-17-8) + C22H28O5 (1363502-03-7)

Guidance literature:

With Aspergillus ochraceus SIT₃₄₂₀₅; at 28 ℃; for 50h;

DOI:10.1016/j.cclet.2012.01.003

Reference yield:

→ 11α-hydroxyl canrenone (192569-17-8)

Guidance literature:

upstream raw materials:

canrenone

Downstream raw materials:

4'S(4'α),7'α-hexadecahydro-11'α-hydroxy-10'β,13'β-dimethyl-3',5,20'-trioxospiro[furan-2(3H),17'β-[4,7]metheno(17H)cyclopenta[a]phenanthrene]-5'β(2'H)-carbonitrile

eplerenone

11β,17β-dihydroxy-7α-methoxycarbonyl-pregna-4-en-3-one-21-carboxylic acid, γ-lactone

methyl hydrogen 17α-hydroxy-11α-(methylsulfonyl)oxy-3-oxopregn-4-ene-7α,21-dicarboxylate, γ-lactone

Refernces

• 1、 Rong, Shao Feng,Zhang, Xiao Li,Ding, Bao Mei,Wang, Yi Fei,Pan, Xian Hua,Zhang, Jian,Shen, Yi. "Structural characterization of 1β,11α-dihydroxycanrenone biotrans-formed from canrenone by Aspergillus ochraceus SIT34205". experimental part. p. 313 - 316. Retrieved 2012/05/05.