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

• ChemBase ID: 177417
• Molecular Formular: C31H32O14
• Molecular Mass: 628.57738
• Monoisotopic Mass: 628.1792057
• SMILES: O([C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)OC)OC(=O)C)OC(=O)C)OC(=O)C)c1cc(cc(c1)/C=C/c1ccc(cc1)OC(=O)C)OC(=O)C
• Canonical SMILES: COC(=O)[C@@H]1O[C@@H](Oc2cc(/C=C/c3ccc(cc3)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)39-23-11-9-21(10-12-23)7-8-22-13-24(40-17(2)33)15-25(14-22)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: QJSVFPKNACJMKM-JEGSXUJPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-[3-(acetyloxy)-5-[(E)-2-[4-(acetyloxy)phenyl]ethenyl]phenoxy]oxane-2-carboxylate
• IUPAC Traditional name: methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-[3-(acetyloxy)-5-[(E)-2-[4-(acetyloxy)phenyl]ethenyl]phenoxy]oxane-2-carboxylate
• Synonyms: 3-(acetyloxy)-5-[(1E)-2-[4-(acetyloxy)phenyl]ethenyl]phenyl-β-D-Glucopyranosiduronic Acid Methyl Ester Triacetate; trans Resveratrol Penta-O-acetyl-3-β-D-glucuronide Methyl Ester

Database IDs

• CAS Number: 490028-22-3
• PubChem SID: 164233327
• PubChem CID: 71752006

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: 60.24612 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

DETAILS

Toronto Research Chemicals - R150030

Intermediate for the synthesis of glucuronide conjugates of trans-Resveratrol

REFERENCES

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