[(2R,3R,4R)-3,4,5-trihydroxy-4-[(3,4,5-trihydroxybenzoyloxy)methyl]oxolan-2-yl]methyl 3,4,5-trihydroxybenzoate

• ChemBase编号: 157297
• 分子式: C20H20O14
• 平均质量: 484.3644
• 单一同位素质量: 484.08530532
• SMILES: c1c(cc(c(c1O)O)O)C(=O)OC[C@@H]1[C@H]([C@@](C(O1)O)(COC(=O)c1cc(c(c(c1)O)O)O)O)O
• Canonical SMILES: O=C(c1cc(O)c(c(c1)O)O)OC[C@H]1OC([C@@]([C@@H]1O)(O)COC(=O)c1cc(O)c(c(c1)O)O)O
• InChI: InChI=1S/C20H20O14/c21-9-1-7(2-10(22)14(9)25)17(28)32-5-13-16(27)20(31,19(30)34-13)6-33-18(29)8-3-11(23)15(26)12(24)4-8/h1-4,13,16,19,21-27,30-31H,5-6H2/t13-,16-,19?,20-/m1/s1
• InChIKey: FEPAFOYQTIEEIS-IZUGRSKYSA-N

名称和登记号

名称

• IUPAC标准名: [(2R,3R,4R)-3,4,5-trihydroxy-4-[(3,4,5-trihydroxybenzoyloxy)methyl]oxolan-2-yl]methyl 3,4,5-trihydroxybenzoate
• IUPAC传统名: [(2R,3R,4R)-3,4,5-trihydroxy-4-[(3,4,5-trihydroxybenzoyloxy)methyl]oxolan-2-yl]methyl 3,4,5-trihydroxybenzoate
• 别名: 2-C-(Hydroxymethyl)-D-ribofuranose 2′,5-digallate; Hamamelofuranose 2′,5-digallate; Hamamelitannin

登记号

• CAS号: 469-32-9
• EC号: 207-416-3
• MDL号: MFCD00017418
• PubChem SID: 24845763; 162251434
• PubChem CID: 16211077

理论计算性质

• Acid pKa: 7.8063464
• 质子受体: 12
• 质子供体: 9
• LogD (pH = 5.5): 0.09854523
• LogD (pH = 7.4): -0.053568732
• Log P: 0.100670196
• 摩尔折射率: 107.6722 cm^3
• 极化性: 42.10978 Å^3
• 极化表面积: 243.9 Å^2
• 可自由旋转的化学键: 8
• 里宾斯基五规则: false

分子性质

安全信息

• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥98.0% (HPLC)
• Empirical Formula (Hill Notation): C20H20O14

详细说明

Sigma Aldrich - 04646

Application
Hamamelitannin can be used to study chromatography, aromatics, esters, hamamelis, heterocyclics, natural compounds, phenols, phytopharma standards, polyhydroxy compounds and tannins. Hamamelitannin significantly reduces biofilm metabolic activity of the following bacteria: Staphylococcus epidermidis, Staphylococcus aureus, Acinetobacter baumannii and Candida albicans strains. Hamamelitannin displays specific cytotoxic activity against colon cancer cells. Hamamelitannin has been used in a study to determine that quorum sensing inhibitors increase the success of antibiotic treatment by increasing the susceptibility of bacterial biofilms and/or by increasing host survival following infection.