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

• ChemBase编号: 73013
• 分子式: C20H22O8
• 平均质量: 390.38388
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (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传统名: piceid; (2S,3R,4S,5S,6R)-2-{3-hydroxy-5-[2-(4-hydroxyphenyl)ethenyl]phenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• 别名: 3,4′-5-三羟基二苯乙烯-3-β-D-吡喃葡萄糖苷; 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

登记号

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

理论计算性质

• Acid pKa: 9.101978
• 质子受体: 8
• 质子供体: 6
• LogD (pH = 5.5): 1.1342149
• LogD (pH = 7.4): 1.1257933
• Log P: 1.1343228
• 摩尔折射率: 99.5999 cm^3
• 极化性: 38.961105 Å^3
• 极化表面积: 139.84 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: false

分子性质

理化性质

• 熔点: 223-226 °C(lit.)
• 比旋光度: [α]20/D -55°, c = 1 in acetone

安全信息

• 保存条件: -20°C
• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

产品相关信息

• 纯度: 97%
• 成盐信息: Free Base
• Empirical Formula (Hill Notation): C20H22O8

详细说明

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

包装
1 g in glass bottle

参考文献

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