2-oxo-2-[(1S,2S,10S,11S,13S,14R,15S,17S)-2,13,15-trimethyl-5-oxo-14-(propanoyloxy)-18-oxapentacyclo[8.8.0.01,17.02,7.011,15]octadeca-3,6-dien-14-yl]ethyl propanoate

• ChemBase ID: 162015
• Molecular Formular: C28H36O7
• Molecular Mass: 484.58124
• Monoisotopic Mass: 484.24610349
• SMILES: C1=C[C@]2(C(=CC1=O)CC[C@@H]1[C@]32[C@H](C[C@]2([C@H]1C[C@@H]([C@@]2(C(=O)COC(=O)CC)OC(=O)CC)C)C)O3)C
• Canonical SMILES: CCC(=O)O[C@@]1([C@@H](C)C[C@@H]2[C@]1(C)C[C@@H]1O[C@@]31[C@H]2CCC1=CC(=O)C=C[C@]31C)C(=O)COC(=O)CC
• InChI: InChI=1S/C28H36O7/c1-6-23(31)33-15-21(30)27(35-24(32)7-2)16(3)12-20-19-9-8-17-13-18(29)10-11-25(17,4)28(19)22(34-28)14-26(20,27)5/h10-11,13,16,19-20,22H,6-9,12,14-15H2,1-5H3/t16-,19-,20-,22-,25-,26-,27-,28+/m0/s1
• InChIKey: BWSCDDHHJUGBSQ-XHYJHYNESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-oxo-2-[(1S,2S,10S,11S,13S,14R,15S,17S)-2,13,15-trimethyl-5-oxo-14-(propanoyloxy)-18-oxapentacyclo[8.8.0.0^1,^1^7.0^2,^7.0^1^1,^1^5]octadeca-3,6-dien-14-yl]ethyl propanoate
• IUPAC Traditional name: 2-oxo-2-[(1S,2S,10S,11S,13S,14R,15S,17S)-2,13,15-trimethyl-5-oxo-14-(propanoyloxy)-18-oxapentacyclo[8.8.0.0^1,^1^7.0^2,^7.0^1^1,^1^5]octadeca-3,6-dien-14-yl]ethyl propanoate
• Synonyms: (9β,11β,16β)-9,11-Epoxy-16-methyl-17,21-bis(1-oxopropoxy)pregna-1,4-diene-3,20-dione; Beclomethasone 9,11-Epoxide 17,21-Dipropionate; Betamethasone 9β,11β-epoxide 17,21-Dipropionate; Betamethasone 9,11-Epoxide 17,21-Dipropionate

Database IDs

• CAS Number: 66917-44-0
• PubChem SID: 162256150
• PubChem CID: 22821921

CALCULATED PROPERTIES

• Acid pKa: 15.566581
• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 4.235504
• LogD (pH = 7.4): 4.235504
• Log P: 4.235504
• Molar Refractivity: 128.2317 cm^3
• Polarizability: 50.58623 Å^3
• Polar Surface Area: 99.27 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 143-145°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - B327060

Betamethasone (B327000) impurity, as antiinflammatory agent.

REFERENCES

• Shou, M., et al.: J. Pharm. Biomed. Anal., 50, 356 (2009)