(1'S,2R,2'S,4'S,5R,7'S,8'R,9'S,12'S,13'R,16'R)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.02,9.04,8.013,18]icosan]-18'-en-16'-yl benzoate

• ChemBase ID: 160951
• Molecular Formular: C34H46O4
• Molecular Mass: 518.72664
• Monoisotopic Mass: 518.33960995
• SMILES: C1[C@H](CC2=CC[C@@H]3[C@@H]([C@]2(C1)C)CC[C@]1([C@H]3C[C@H]2[C@@H]1[C@@H]([C@@]1(O2)OC[C@@H](CC1)C)C)C)OC(=O)c1ccccc1
• Canonical SMILES: C[C@@H]1CC[C@@]2(OC1)O[C@@H]1[C@H]([C@@H]2C)[C@@]2([C@@H](C1)[C@@H]1CC=C3[C@]([C@H]1CC2)(C)CC[C@H](C3)OC(=O)c1ccccc1)C
• InChI: InChI=1S/C34H46O4/c1-21-12-17-34(36-20-21)22(2)30-29(38-34)19-28-26-11-10-24-18-25(37-31(35)23-8-6-5-7-9-23)13-15-32(24,3)27(26)14-16-33(28,30)4/h5-10,21-22,25-30H,11-20H2,1-4H3/t21-,22+,25-,26-,27+,28+,29+,30+,32+,33+,34-/m1/s1
• InChIKey: CWUJEAGCIAAOMQ-RTDPTVCESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1'S,2R,2'S,4'S,5R,7'S,8'R,9'S,12'S,13'R,16'R)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icosan]-18'-en-16'-yl benzoate
• IUPAC Traditional name: (1'S,2R,2'S,4'S,5R,7'S,8'R,9'S,12'S,13'R,16'R)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icosan]-18'-en-16'-yl benzoate
• Synonyms: (3β,25R)-Spirost-5-en-3-ol Benzoate; Diosgenin Benzoate; 3-O-Benzoyl Diosgenine

Database IDs

• CAS Number: 4952-68-5
• PubChem SID: 162255086
• PubChem CID: 71313554

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 7.4226055
• LogD (pH = 7.4): 7.4226055
• Log P: 7.4226055
• Molar Refractivity: 150.0879 cm^3
• Polarizability: 59.40486 Å^3
• Polar Surface Area: 44.76 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• Apperance: White Solid
• Melting Point: 232-234°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - B208120

Protected Diosgenine.

REFERENCES

• Liu, Y., et al.: Bioorg. Med. Chem. Lett., 17, 156 (2007)