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

• ChemBase ID: 159430
• Molecular Formular: C29H30O13
• Molecular Mass: 586.5407
• Monoisotopic Mass: 586.16864102
• 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)O
• Canonical SMILES: COC(=O)[C@@H]1O[C@@H](Oc2cc(/C=C\c3ccc(cc3)OC(=O)C)cc(c2)O)[C@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C29H30O13/c1-15(30)37-22-10-8-19(9-11-22)6-7-20-12-21(34)14-23(13-20)41-29-27(40-18(4)33)25(39-17(3)32)24(38-16(2)31)26(42-29)28(35)36-5/h6-14,24-27,29,34H,1-5H3/b7-6-/t24-,25-,26-,27+,29+/m0/s1
• InChIKey: LZLFIVXCHYMMKA-XMDCALFISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-{3-[(Z)-2-[4-(acetyloxy)phenyl]ethenyl]-5-hydroxyphenoxy}oxane-2-carboxylate
• IUPAC Traditional name: methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-{3-[(Z)-2-[4-(acetyloxy)phenyl]ethenyl]-5-hydroxyphenoxy}oxane-2-carboxylate
• Synonyms: 4'-O-Acetyl cis Resveratrol 3-O-β-D-Glucuronide Methyl Ester Triacetate

Database IDs

• PubChem SID: 162253565
• PubChem CID: 71312981

CALCULATED PROPERTIES

• Acid pKa: 9.32687
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): 2.8346295
• LogD (pH = 7.4): 2.8296168
• Log P: 2.834694
• Molar Refractivity: 140.8424 cm^3
• Polarizability: 56.397026 Å^3
• Polar Surface Area: 170.19 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate
• Apperance: White Foam

DETAILS

Toronto Research Chemicals - A187690

Intermediate in the preparation of cis Resveratrol metabolite.