2,3,4,6-tetraacetyl-3,4,5-trimethoxyphenyl-β-D-glucoside | 108543-42-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetraacetyl-3,4,5-trimethoxyphenyl-β-D-glucoside
• 英文别名: 3,4,5-Trimethoxyphenoltetraacetyl-β-D-glucopyranoside；[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-(3,4,5-trimethoxyphenoxy)oxan-2-yl]methyl acetate
• CAS: 108543-42-6
• 化学式: C₂₃H₃₀O₁₃
• 分子量: 514.483
• InChiKey: NLKKHZDQGNSHOS-DODNOZFWSA-N

物化性质

• 沸点：
  570.8±50.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  36
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  151
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetraacetyl-3,4,5-trimethoxyphenyl-β-D-glucoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以290 mg的产率得到3,4,5-三甲氧基苯基 beta-D-吡喃葡萄糖苷
  参考文献：
  名称：

  In Vitro Antiplasmodial Activity of Extracts of Tristaniopsis Species and Identification of the Active Constituents:  Ellagic Acid and 3,4,5-Trimethoxyphenyl-(6‘-O-galloyl)-O-β-d-glucopyranoside

  摘要：

  Screening of plants from New Caledonia for antiplasmodial activity against Plasmodium falciparum revealed that methanolic extracts of the leaves and bark of Tristaniopsis calobuxus, T. yateensis, and T. glauca inhibited the growth of chloroquine-sensitive and -resistant clones. Ellagic acid and the new compound 3,4,5-trimethoxyphenyl-(6 ' -O-galloyl)-O-beta -D-glucopyranoside were identified as the active constituents (IC50 0.5 and 3.2 muM, respectively). The growth inhibition of both clones was comparable. The compounds showed negligible or very low cytotoxicity to human skin fibroblasts and Hep G2 cells when tested at concentrations ranging from 0.5 to 100 muM.

  DOI：

  10.1021/np000306j
• 作为产物：
  描述：

  3,4,5-三甲氧基苯胺 在 sodium hydroxide 、 硫酸 、 苄基三乙基氯化铵 、 copper(II) sulfate 、 sodium nitrite 作用下， 以 氯仿 为溶剂， 反应 24.25h， 生成 2,3,4,6-tetraacetyl-3,4,5-trimethoxyphenyl-β-D-glucoside
  参考文献：
  名称：

  In Vitro Antiplasmodial Activity of Extracts of Tristaniopsis Species and Identification of the Active Constituents:  Ellagic Acid and 3,4,5-Trimethoxyphenyl-(6‘-O-galloyl)-O-β-d-glucopyranoside

  摘要：

  Screening of plants from New Caledonia for antiplasmodial activity against Plasmodium falciparum revealed that methanolic extracts of the leaves and bark of Tristaniopsis calobuxus, T. yateensis, and T. glauca inhibited the growth of chloroquine-sensitive and -resistant clones. Ellagic acid and the new compound 3,4,5-trimethoxyphenyl-(6 ' -O-galloyl)-O-beta -D-glucopyranoside were identified as the active constituents (IC50 0.5 and 3.2 muM, respectively). The growth inhibition of both clones was comparable. The compounds showed negligible or very low cytotoxicity to human skin fibroblasts and Hep G2 cells when tested at concentrations ranging from 0.5 to 100 muM.

  DOI：

  10.1021/np000306j

文献信息

• Phenolic glucosides from Parabenzoin praecox
  作者：Hiroko Shimomura、Yutaka Sashida、Motomu Oohara、Hiroko Tenma

  DOI：10.1016/0031-9422(88)83166-2

  日期：1988.1

  Abstract From the methanolic extract of the bark of Parabenzoin praecox (Sieb. et Zucc.) Nakai, a new phenolic glucoside ester, 4-(2-nitroethyl)phenyl β- d -(6- O -caffeoyl)glucopyranoside, and a new phenolic glucoside, 3,4,5-trimethoxyphenyl β- d -glucopyranoside have been isolated together with a known compound, thalictoside. The structures of these compounds have been determined on the basis of

  摘要 从对苯并英 (Sieb. et Zucc.) Nakai 树皮的甲醇提取物中，一种新的酚糖苷酯、4-(2-硝基乙基)苯基 β-d-(6-O-咖啡酰) 吡喃葡萄糖苷和一种新的酚糖苷、3,4,5-三甲氧基苯基β-d-吡喃葡萄糖苷已与已知化合物沙梨糖苷一起分离。这些化合物的结构是在光谱研究和化学证据的基础上确定的。
• FUKAYA, TSUTOMU;SIRAKAMI, XIRONARI;AKIRA, TOSIAKI;IVAI, MASAKADZU;IGA, IO+
  作者：FUKAYA, TSUTOMU、SIRAKAMI, XIRONARI、AKIRA, TOSIAKI、IVAI, MASAKADZU、IGA, IO+

  DOI：——

  日期：——
• In Vitro Antiplasmodial Activity of Extracts of <i>Tristaniopsis </i>Species and Identification of the Active Constituents:  Ellagic Acid and 3,4,5-Trimethoxyphenyl-(6‘-<i>O</i>-galloyl)-<i>O</i>-β-<scp>d</scp>-glucopyranoside
  作者：Luisella Verotta、Mario Dell'Agli、Andrea Giolito、Marco Guerrini、Pierre Cabalion、Enrica Bosisio

  DOI：10.1021/np000306j

  日期：2001.5.1

  Screening of plants from New Caledonia for antiplasmodial activity against Plasmodium falciparum revealed that methanolic extracts of the leaves and bark of Tristaniopsis calobuxus, T. yateensis, and T. glauca inhibited the growth of chloroquine-sensitive and -resistant clones. Ellagic acid and the new compound 3,4,5-trimethoxyphenyl-(6 ' -O-galloyl)-O-beta -D-glucopyranoside were identified as the active constituents (IC50 0.5 and 3.2 muM, respectively). The growth inhibition of both clones was comparable. The compounds showed negligible or very low cytotoxicity to human skin fibroblasts and Hep G2 cells when tested at concentrations ranging from 0.5 to 100 muM.