(R)-2-(3-(3,4-dihydroxyphenyl)acryloyloxy)-3-(6-ethoxy-4,7-dioxo-4,7-dihydrooxepin-3-yl)propanoic acid | 1261066-10-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (R)-2-(3-(3,4-dihydroxyphenyl)acryloyloxy)-3-(6-ethoxy-4,7-dioxo-4,7-dihydrooxepin-3-yl)propanoic acid
• 英文别名: (2R)-2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3-(6-ethoxy-4,7-dioxooxepin-3-yl)propanoic acid
• CAS: 1261066-10-7
• 化学式: C₂₀H₁₈O₁₀
• 分子量: 418.357
• InChiKey: SKJXNQRZYGWNQO-MQDFFIGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  157
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  乙醇 、 迷迭香酸 在 iron(III) chloride 、 氧气 作用下， 反应 120.0h， 生成 (R)-2-(3-(3,4-dihydroxyphenyl)acryloyloxy)-3-(6-ethoxy-4,7-dioxo-4,7-dihydrooxepin-3-yl)propanoic acid
  参考文献：
  名称：

  A novel ring-expanded product with enhanced tyrosinase inhibitory activity from classical Fe-catalyzed oxidation of rosmarinic acid, a potent antioxidative Lamiaceae polyphenol

  摘要：

  The iron-ion catalyzed oxidation of the ethanol solution of rosmarinic acid, a potent antioxidant polyphenol of Lamiaceae (Labiatae) plants, afforded a highly tyrosinase-inhibitory active product. The structure of the active product in the oxidation product mixture was determined using extensive NMR spectroscopy to have a novel oxygen-containing seven-membered ring system. The formation mechanism of the unique ring structure from the catechol part of the rosmarinic acid was proposed. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.10.040