5-Hydroxydrospirenone

Base Information

• Chemical Name: 5-Hydroxydrospirenone
• CAS No.: 197721-70-3
• Molecular Formula: C24H32O4
• Molecular Weight: 384.516
• European Community (EC) Number: 606-376-8
• UNII: AC1T1MJ4XN
• DSSTox Substance ID: DTXSID50173470
• Wikidata: Q27273859
• Mol file: 197721-70-3.mol

Synonyms:5-Hydroxydrospirenone;197721-70-3;UNII-AC1T1MJ4XN;AC1T1MJ4XN;5beta-Hydroxy Drospirenone;EC 606-376-8;(1R,2R,4R,5R,10R,11S,14S,15S,16S,18S,19S)-5-hydroxy-10,14-dimethylspiro[hexacyclo[9.8.0.02,4.05,10.014,19.016,18]nonadecane-15,5'-oxolane]-2',7-dione;5-Hydroxy-6 beta,7 beta;15 beta,16 beta-dimethylene-3-oxo-5 beta,17 alpha-pregnane-21,17-carbolactone;5b-Hydroxy Drospirenone;5|A-Hydroxy Drospirenone;DTXSID50173470;Q27273859;DROSPIRENONE IMPURITY, 5-HYDROXYDROSPIRENONE- [USP IMPURITY];5.BETA.,17.BETA.-DIHYDROXY-6.BETA.,7.BETA.:15.BETA.,16.BETA.-DIMETHYLENE-17.ALPHA.-PREGNAN-21-CARBOXYLIC ACID, -GAMMA.LACTONE;SPIRO(17H-DICYCLOPROPA(6,7:15,16)CYCLOPENTA(A)PHENANTHRENE-17,2'(5'H)-FURAN)-3,5'(2H)-DIONE, OCTADECAHYDRO-5-HYDROXY-10,13-DIMETHYL-, (2'S,5R,6R,7R,8R,9S,10R,13S,14S,15S,16S)-;SPIRO(17H-DICYCLOPROPA(6,7:15,16)CYCLOPENTA(A)PHENANTHRENE-17,2'(5'H)-FURAN)-3,5'(2H)-DIONE, OCTADECAHYDRO-5-HYDROXY-10,13-DIMETHYL-, (5R-(5.ALPHA.,6.BETA.,7.BETA.,8.ALPHA.,9.BETA.,10.ALPHA.,13.ALPHA.,14.BETA.,15.BETA.,16.BETA.,17.ALPHA.))-

Chemical Property of 5-Hydroxydrospirenone

Chemical Property:

• Boiling Point: 565.3±50.0 °C(Predicted)
• PKA: 14.01±0.60(Predicted)
• PSA: 63.60000
• Density: 1.30±0.1 g/cm3(Predicted)
• LogP: 3.50070
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility.: Dichloromethane (Slightly), Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: 93mg/L at 20℃
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 384.23005950
• Heavy Atom Count: 28
• Complexity: 821

Purity/Quality:

99.9% ^*data from raw suppliers

5β-HydroxyDrospirenone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(=O)CC1(C3CC3C4C2CCC5(C4C6CC6C57CCC(=O)O7)C)O
• Isomeric SMILES: C[C@]12CCC(=O)C[C@]1([C@@H]3C[C@@H]3[C@@H]4[C@@H]2CC[C@]5([C@H]4[C@@H]6C[C@@H]6[C@@]57CCC(=O)O7)C)O
• Uses: 5β-Hydroxy Drospirenone is an impurity of Drospirenone (D689500).

Technology Process of 5-Hydroxydrospirenone

There total 2 articles about 5-Hydroxydrospirenone 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:

17α-(3-hydroxypropyl)-6β,7β;15β,16β-dimethylene-5β-androstane-3β,5,17β-triol (82543-18-8) → 5β-hydroxy-3-carbonyl-6β,7β,5β,16β-dimethylene-17α-pregna-21,17-carboxylactone (197721-70-3) + dihydrospirorenone (90457-65-1,93920-59-3,67372-75-2,67392-87-4)

Guidance literature:

With 1-hydroxy-1,2-dihydro-3H-1λ3-benziodol-3-one 1-oxide; In dimethyl sulfoxide; N,N-dimethyl-formamide; at 20 - 60 ℃; Product distribution / selectivity;

Reference yield:

17α-(3-hydroxy-1-propinyl)-6β,7β;15β,16β-dimethylene-5β-androstane-3β,5,17β-triol (82543-17-7) → 5β-hydroxy-3-carbonyl-6β,7β,5β,16β-dimethylene-17α-pregna-21,17-carboxylactone (197721-70-3)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogen; palladium 10% on activated carbon / ethanol / 20 - 30 °C

2: dihydrogen peroxide / N,N-dimethyl-formamide; acetone / 35 - 40 °C

With palladium 10% on activated carbon; hydrogen; dihydrogen peroxide; In ethanol; N,N-dimethyl-formamide; acetone;

Reference yield: 77.0%

5β-hydroxy-3-carbonyl-6β,7β,5β,16β-dimethylene-17α-pregna-21,17-carboxylactone (197721-70-3) → dihydrospirorenone (90457-65-1,93920-59-3,67372-75-2,67392-87-4)

Guidance literature:

With phosphorus pentoxide; acetic acid; In tetrahydrofuran; at 20 ℃; for 3h;

upstream raw materials:

17α-(3-hydroxypropyl)-6β,7β;15β,16β-dimethylene-5β-androstane-3β,5,17β-triol

17α-(3-hydroxy-1-propinyl)-6β,7β;15β,16β-dimethylene-5β-androstane-3β,5,17β-triol

Downstream raw materials:

dihydrospirorenone

Refernces

• 1、 -. "Process for the preparation of drospirenone". Paragraph 0031-0039. . Retrieved 2013/03/26.
• 2、 -. "METHODS FOR THE PREPARATION OF DROSPIRENONE AND INTERMEDIATES THEREOF". Page/Page column 19; 20. . Retrieved 2012/02/15.