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

• ChemBase ID: 73013
• Molecular Formular: C20H22O8
• Molecular Mass: 390.38388
• Monoisotopic Mass: 390.13146766
• SMILES: [C@@H]1([C@@H]([C@H](O[C@H]([C@@H]1O)Oc1cc(cc(c1)/C=C/c1ccc(cc1)O)O)CO)O)O
• Canonical SMILES: OC[C@H]1O[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/b2-1+/t16-,17-,18+,19-,20-/m1/s1
• InChIKey: HSTZMXCBWJGKHG-CUYWLFDKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4S,5S,6R)-2-{3-hydroxy-5-[(E)-2-(4-hydroxyphenyl)ethenyl]phenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol; (2S,3R,4S,5S,6R)-2-{3-hydroxy-5-[2-(4-hydroxyphenyl)ethenyl]phenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: piceid; (2S,3R,4S,5S,6R)-2-{3-hydroxy-5-[2-(4-hydroxyphenyl)ethenyl]phenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• Synonyms: Piceid; 3; 4; 5-Tsg; 5-Trihydroxystilbene-3-beta-monoglucoside; Polydatin(Piceid); 3,4′-5-Trihydroxystilbene-3-β-D-glucopyranoside; (2S,3R,4S,5S,6R)-2-(3-hydroxy-5-((E)-4-hydroxystyryl)phenoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol; 3,4′-5-三羟基二苯乙烯-3-β-D-吡喃葡萄糖苷

Database IDs

• CAS Number: 65914-17-2
• MDL Number: MFCD00210592
• PubChem SID: 162037933; 24880655
• PubChem CID: 5281718

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

• Melting Point: 223-226 °C(lit.)
• Optical Rotation: [α]20/D -55°, c = 1 in acetone

Safety Information

• Storage Condition: -20°C
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 97%
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C20H22O8

DETAILS

Selleck Chemicals - S2390

Research Area: Cardiovascular Disease
Biological Activity:
Polydatin(Piceid), 3,4’,5-trihydroxystilbene-3-β-mono-D-glucoside, the crystal component extracted from the root stem of perennial herbage Polygonum Cuspidatum Sieb.et Zucc. Polydatin protects cerebral cells from ischemic damages via improvement of microcirculation and inhibition of platelet aggregation. In addition, polydatin inhibits ICAM-1 expression in endothelial cells stimulated by lipopolysaccharide; it also attenuates adhesion between white blood cells and endothelial cells. [1]

Sigma Aldrich - 572691

Packaging
1 g in glass bottle

REFERENCES

• Cheng Y, et al. Brain Res. 2006 Sep 19;1110(1):193-200.