(2S,4S,5S)-2-{3-hydroxy-5-[(E)-2-(4-hydroxyphenyl)ethenyl]phenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

• ChemBase ID: 177428
• Molecular Formular: C20H22O8
• Molecular Mass: 390.38388
• Monoisotopic Mass: 390.13146766
• SMILES: [C@@H]1([C@@H](C([C@@H](OC1CO)Oc1cc(cc(c1)/C=C/c1ccc(cc1)O)O)O)O)O
• Canonical SMILES: OCC1O[C@@H](Oc2cc(/C=C/c3ccc(cc3)O)cc(c2)O)C([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C20H22O8/c21-10-16-17(24)18(25)19(26)20(28-16)27-15-8-12(7-14(23)9-15)2-1-11-3-5-13(22)6-4-11/h1-9,16-26H,10H2/b2-1+/t16?,17-,18+,19?,20-/m1/s1
• InChIKey: HSTZMXCBWJGKHG-GHHIHIOFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4S,5S)-2-{3-hydroxy-5-[(E)-2-(4-hydroxyphenyl)ethenyl]phenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: (2S,4S,5S)-2-{3-hydroxy-5-[(E)-2-(4-hydroxyphenyl)ethenyl]phenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• Synonyms: 3-Hydroxy-5-[(1E)-2-(4-hydroxyphenyl)ethenyl]phenyl β-D-Glucopyranoside; Piceid; (E)-Piceid; (E)-Polydatin; 3-Hydroxy-5-(p-hydroxystyryl)phenyl β-D-Glucoside; E-Resveratrol 3-O-Glucopyranoside; Pieceid; Polydatin; Polydotin Peceid; Resveratrol 3-O-β-D-Glucoside; Resveratrol 3-O-β-Glucopyranoside; trans-Piceid; trans-Polydatin; trans Resveratrol 3-O-β-D-glucopyranoside, 98%

Database IDs

• CAS Number: 27208-80-6
• PubChem SID: 164233338
• PubChem CID: 71752015

CALCULATED PROPERTIES

• Acid pKa: 9.101978
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): 1.1342149
• LogD (pH = 7.4): 1.1257933
• Log P: 1.1343228
• Molar Refractivity: 99.5999 cm^3
• Polarizability: 38.961105 Å^3
• Polar Surface Area: 139.84 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Ethanol; Methanol
• Apperance: Off-White Solid
• Melting Point: 217-219°C

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - R150080

A Stilbenoid glucoside and is a major Resveratrol derivative.

REFERENCES

• Jeong, E., et al.: Arch. Pharm. Res., 33, 1331 (2010)
• Larrosa, M., et al.: J. Med. Chem., 53, 7365 (2010)
• Nguyen, T., et al.: Food Chem., 124, 437 (2010)