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

• ChemBase ID: 154126
• Molecular Formular: C20H22O8
• Molecular Mass: 390.38388
• Monoisotopic Mass: 390.13146766
• SMILES: c1cc(ccc1/C=C/c1cc(cc(c1)O[C@H]1[C@@H]([C@H]([C@@H](C(O1)CO)O)O)O)O)O
• Canonical SMILES: OCC1O[C@@H](Oc2cc(/C=C/c3ccc(cc3)O)cc(c2)O)[C@@H]([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/t16?,17-,18+,19-,20-/m1/s1
• InChIKey: HSTZMXCBWJGKHG-DGDSNLKDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4S,5S)-2-{3-hydroxy-5-[2-(4-hydroxyphenyl)ethenyl]phenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: (2S,3R,4S,5S)-2-{3-hydroxy-5-[2-(4-hydroxyphenyl)ethenyl]phenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• Synonyms: Piceid; Reservatrol-3-β-mono-D-glucoside; Resveratrol 3-O-β-D-glucopyranoside; Polydatin

Database IDs

• CAS Number: 65914-17-2
• Beilstein Number: 54837
• PubChem SID: 162248265
• PubChem CID: 71311798

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

• Optical Rotation: [α]1/D -66.0±2.0° in ethanol

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥95% (HPLC)
• Compostion: carbon, 60.5-62.5%
• Empirical Formula (Hill Notation): C20H22O8

DETAILS

Sigma Aldrich - 15721

Biochem/physiol Actions
Stilbene found in medicinal herbs. Antioxidant, anti-inflammatory and neuroprotective.
Application
Polydatin, a type of polyphenolic phytoalexin, has many physiological and pharmacological effects including anti-inflammatory and anti-oxidative activities. Polydatin is an effective candidate drug for the protection of photo-inflammation. Polydatin exhibits therapeutic potential for vascular dementia, most likely due to its anti-oxidant activity and the direct protection of neurons.