methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-[2-(methoxycarbonyl)phenoxy]oxane-2-carboxylate

• ChemBase ID: 174323
• Molecular Formular: C21H24O12
• Molecular Mass: 468.40806
• Monoisotopic Mass: 468.12677621
• SMILES: O1[C@@H](Oc2ccccc2C(=O)OC)[C@H]([C@H]([C@@H]([C@@H]1C(=O)OC)OC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: COC(=O)[C@@H]1O[C@@H](Oc2ccccc2C(=O)OC)[C@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C21H24O12/c1-10(22)29-15-16(30-11(2)23)18(31-12(3)24)21(33-17(15)20(26)28-5)32-14-9-7-6-8-13(14)19(25)27-4/h6-9,15-18,21H,1-5H3/t15-,16-,17-,18+,21+/m0/s1
• InChIKey: GCFDADXDOSHULB-ARWBCWGVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-[2-(methoxycarbonyl)phenoxy]oxane-2-carboxylate
• IUPAC Traditional name: methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-[2-(methoxycarbonyl)phenoxy]oxane-2-carboxylate
• Synonyms: 2-(Methoxycarbonyl)phenyl β-D-Glucopyranosiduronic Acid Methyl Triacetate Ester; Ο-carboxyphenyl β-D-Glucopyranosiduronic Αcid Triacetate Dimethyl Ester.; Methyl Salicylate β-D-O-Glucuronide Triacetate Methyl Ester

Database IDs

• CAS Number: 101231-54-3
• PubChem SID: 164230233
• PubChem CID: 71750606

CALCULATED PROPERTIES

• H Acceptors: 7
• H Donor: 0
• LogD (pH = 5.5): 1.1946342
• LogD (pH = 7.4): 1.1946342
• Log P: 1.1946342
• Molar Refractivity: 104.2996 cm^3
• Polarizability: 42.738815 Å^3
• Polar Surface Area: 149.96 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethanol; Methanol
• Apperance: Pale-brown Solid

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - M326590

Intermediate in the synthesis of Aspirin metabolite.

REFERENCES

• Grootveld, M., et al.: Biochem. Pharmacol., 37, 271 (1988)
• Subbegowda, R., et al.: Cancer Res., 58, 2772 (1988)
• Yoshida, Y., et al.: Eur. J. Pharmacol., 349, 49 (1988)