methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-{4-[(E)-2-[3,5-bis(acetyloxy)phenyl]ethenyl]phenoxy}oxane-2-carboxylate

• ChemBase ID: 177418
• Molecular Formular: C31H32O14
• Molecular Mass: 628.57738
• Monoisotopic Mass: 628.1792057
• SMILES: O1[C@H]([C@H]([C@H]([C@@H]([C@@H]1C(=O)OC)OC(=O)C)OC(=O)C)OC(=O)C)Oc1ccc(/C=C/c2cc(cc(c2)OC(=O)C)OC(=O)C)cc1
• Canonical SMILES: COC(=O)[C@@H]1O[C@@H](Oc2ccc(cc2)/C=C/c2cc(OC(=O)C)cc(c2)OC(=O)C)[C@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C31H32O14/c1-16(32)39-24-13-22(14-25(15-24)40-17(2)33)8-7-21-9-11-23(12-10-21)44-31-29(43-20(5)36)27(42-19(4)35)26(41-18(3)34)28(45-31)30(37)38-6/h7-15,26-29,31H,1-6H3/b8-7+/t26-,27-,28-,29+,31+/m0/s1
• InChIKey: HGHYMWJYXANQKR-JEGSXUJPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-{4-[(E)-2-[3,5-bis(acetyloxy)phenyl]ethenyl]phenoxy}oxane-2-carboxylate
• IUPAC Traditional name: methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-{4-[(E)-2-[3,5-bis(acetyloxy)phenyl]ethenyl]phenoxy}oxane-2-carboxylate
• Synonyms: 4-[(1E)-2-[3,5-Bis(acetyloxy)phenyl]ethenyl]phenyl-β-D-glucopyranosiduronic Acid Methyl Ester Triacetate; (E)-1-(3,5-Diacetoxyphenyl)-2-(4’-O-2,3,4-triacetyl-β-D-glucuronopyranosidophenyl)ethene Methyl Ester; trans Resveratrol Penta-O-acetyl-4'-β-D-glucuronide Methyl Ester

Database IDs

• CAS Number: 490028-19-8
• PubChem SID: 164233328
• PubChem CID: 71752007

CALCULATED PROPERTIES

• H Acceptors: 8
• H Donor: 0
• LogD (pH = 5.5): 2.74552
• LogD (pH = 7.4): 2.74552
• Log P: 2.74552
• Molar Refractivity: 149.9939 cm^3
• Polarizability: 60.2461 Å^3
• Polar Surface Area: 176.26 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Ethyl Acetate; Methanol
• Apperance: Off-White Solid

DETAILS

Toronto Research Chemicals - R150035

Intermediate for the synthesis of glucuronide conjugates of trans-Resveratrol

REFERENCES

• Learmonth, D.A., et al.: Bioconjug. Chem., 14, 262 (2003)