3-(4-acetoxy-3-methoxyphenyl)-6-[3,5,7-triacetoxy-4-oxochroman-2-yl]-2,3-dihydro-1,4-benzodioxine-2-carboxylic acid | 802918-32-7

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 黄酮木脂素
• 英文名称: 3-(4-acetoxy-3-methoxyphenyl)-6-[3,5,7-triacetoxy-4-oxochroman-2-yl]-2,3-dihydro-1,4-benzodioxine-2-carboxylic acid
• 英文别名: 3,5,7,20-tetra-O-acetylsilybinic acid
• CAS: 802918-32-7
• 化学式: C₃₃H₂₈O₁₅
• 分子量: 664.576
• InChiKey: CEQSIPXXFBJWMD-UJWVPZRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.68
• 重原子数：
  48.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  196.49
• 氢给体数：
  1.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  3-(4-acetoxy-3-methoxyphenyl)-6-[3,5,7-triacetoxy-4-oxochroman-2-yl]-2,3-dihydro-1,4-benzodioxine-2-carboxylic acid 在 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以70%的产率得到3-(4-hydroxy-3-methoxyphenyl)-6-(3,5,7-trihydroxy-4-oxochroman-2-yl)-2,3-dihydro-1,4-benzodioxine-2-carboxylic acid
  参考文献：
  名称：

  Oxidised derivatives of silybin and their antiradical and antioxidant activity

  摘要：

  Carboxylic acids derived from silybin (1) and 2,3-dehydrosilybin (2) with improved water solubility were prepared by selective oxidation of parent compounds and a new inexpensive method for preparation of 2,3-dehydrosilybin from silybin was developed and optimised. The antioxidative properties of the above-mentioned compounds and of side product 3a from oxidation of compound 1 were determined by cyclic voltammetry, free radical scavenging (DPPH, superoxide) assays, and by inhibition of in vitro generated liver microsomal lipid peroxidation. Dehydrogenation at C-(2)-C-(3) in flavonolignans (silybin vs 2,3-dehydrosilybin; silybinic acid vs 2,3-dehydrosilybinic acid) strongly improved antioxidative properties (analogously as in flavonoids taxifolin vs quercetin). Thus, in antioxidative properties, dehydrosilybin was superior to silybin by one order, but its water solubility is too low for application in aqueous milieu. On the other hand, 2,3-dehydrosilybinic acid is a fairly soluble derivative with antilipoperoxidation and antiradical activities better than that of silybin. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.07.064
• 作为产物：
  描述：

  水飞蓟素A,B 在 吡啶 、 chromium(VI) oxide 、 三氟化硼乙醚 、 silver nitrate 、 高碘酸 作用下， 以 氯仿 、 水 、 乙腈 为溶剂， 反应 38.75h， 生成 3-(4-acetoxy-3-methoxyphenyl)-6-[3,5,7-triacetoxy-4-oxochroman-2-yl]-2,3-dihydro-1,4-benzodioxine-2-carboxylic acid
  参考文献：
  名称：

  Oxidised derivatives of silybin and their antiradical and antioxidant activity

  摘要：

  Carboxylic acids derived from silybin (1) and 2,3-dehydrosilybin (2) with improved water solubility were prepared by selective oxidation of parent compounds and a new inexpensive method for preparation of 2,3-dehydrosilybin from silybin was developed and optimised. The antioxidative properties of the above-mentioned compounds and of side product 3a from oxidation of compound 1 were determined by cyclic voltammetry, free radical scavenging (DPPH, superoxide) assays, and by inhibition of in vitro generated liver microsomal lipid peroxidation. Dehydrogenation at C-(2)-C-(3) in flavonolignans (silybin vs 2,3-dehydrosilybin; silybinic acid vs 2,3-dehydrosilybinic acid) strongly improved antioxidative properties (analogously as in flavonoids taxifolin vs quercetin). Thus, in antioxidative properties, dehydrosilybin was superior to silybin by one order, but its water solubility is too low for application in aqueous milieu. On the other hand, 2,3-dehydrosilybinic acid is a fairly soluble derivative with antilipoperoxidation and antiradical activities better than that of silybin. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.07.064