(2R,2'R,15'S,17'R)-17'-hydroxy-2',15'-dimethylspiro[oxolane-2,14'-tetracyclo[8.7.0.02,7.011,15]heptadecane]-6',8'-diene-5,5'-dione

• ChemBase ID: 170318
• Molecular Formular: C22H28O4
• Molecular Mass: 356.45532
• Monoisotopic Mass: 356.19875938
• SMILES: C1C(=O)C=C2[C@](C1)(C1C(C=C2)C2[C@](C[C@H]1O)([C@]1(CC2)OC(=O)CC1)C)C
• Canonical SMILES: O=C1CC[C@]2(C(=C1)C=CC1C2[C@H](O)C[C@]2(C1CC[C@]12CCC(=O)O1)C)C
• InChI: InChI=1S/C22H28O4/c1-20-8-5-14(23)11-13(20)3-4-15-16-6-9-22(10-7-18(25)26-22)21(16,2)12-17(24)19(15)20/h3-4,11,15-17,19,24H,5-10,12H2,1-2H3/t15?,16?,17-,19?,20+,21+,22-/m1/s1
• InChIKey: RJTDWMKVQUPGSY-GOAYFHFKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,2'R,15'S,17'R)-17'-hydroxy-2',15'-dimethylspiro[oxolane-2,14'-tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecane]-6',8'-diene-5,5'-dione
• IUPAC Traditional name: (2R,2'R,15'S,17'R)-17'-hydroxy-2',15'-dimethylspiro[oxolane-2,14'-tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecane]-6',8'-diene-5,5'-dione
• Synonyms: (11α,17α)-11,17-Dihydroxy-3-oxopregna-4,6-diene-21-carboxylic Acid γ-Lactone; 11α-Hydroxy Canrenone

Database IDs

• CAS Number: 192569-17-8
• PubChem SID: 164226228
• PubChem CID: 45358387

CALCULATED PROPERTIES

• Acid pKa: 14.880123
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.286634
• LogD (pH = 7.4): 2.286634
• Log P: 2.286634
• Molar Refractivity: 99.0753 cm^3
• Polarizability: 38.58536 Å^3
• Polar Surface Area: 63.6 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; Methanol
• Apperance: Yellow Solid
• Melting Point: 232-234°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H883500

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.

REFERENCES

• Luetscher, J., et al.: J. Clin. Invest., 29, 1576 (1950)
• Gaunt, R., et al.: J. Clin. Endocrinol. Metab., 15, 621 (1950)
• McMahon, E., et al.: Curr. Opin. Pharm., 1, 190 (1950)
• McMahon, E., et al.: Curr. Pharm. Des., 9, 1065 (1950)