(1S,3R,11R,19S)-19-(3,4-dihydroxyphenyl)-3,11,13,15-tetrahydroxy-2,18-dioxapentacyclo[14.3.1.03,11.04,9.012,17]icosa-4,6,8,12,14,16-hexaen-10-one | 1201920-55-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: (1S,3R,11R,19S)-19-(3,4-dihydroxyphenyl)-3,11,13,15-tetrahydroxy-2,18-dioxapentacyclo[14.3.1.03,11.04,9.012,17]icosa-4,6,8,12,14,16-hexaen-10-one
• CAS: 1201920-55-9
• 化学式: C₂₄H₁₈O₉
• 分子量: 450.402
• InChiKey: MBPQCZVBXFWJOE-FOZDKVSISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  33
• 可旋转键数：
  1
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  157
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  水合茚三酮 、 儿茶提取物 在 三氟甲磺酸三甲基硅酯 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (1S,3R,11R,19S)-19-(3,4-dihydroxyphenyl)-3,11,13,15-tetrahydroxy-2,18-dioxapentacyclo[14.3.1.03,11.04,9.012,17]icosa-4,6,8,12,14,16-hexaen-10-one 、 (1S,3R,11R,19R)-19-(3,4-dihydroxyphenyl)-3,11,13,15-tetrahydroxy-2,18-dioxapentacyclo[14.3.1.03,11.04,9.012,17]icosa-4,6,8,12,14,16-hexaen-10-one
  参考文献：
  名称：

  Novel ninhydrin adduct of catechin with potent antioxidative activity

  摘要：

  The reaction of ninhydrin with (+)-catechin in the presence of TMSOTf resulted in condensation product 1, which consists of a 2:1 mixture of epimers at the C-2 position. The antioxidative radical-scavenging activity of 1 against the galvinoxyl radical, acting as an oxyl radical, was significantly enhanced compared to (+)-catechin. Our results offer a new method for chemical modification of a natural phenolic antioxidant. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.09.149

文献信息

• Novel ninhydrin adduct of catechin with potent antioxidative activity
  作者：Kiyoshi Fukuhara、Akiko Ohno、Ikuo Nakanishi、Kohei Imai、Asao Nakamura、Kazunori Anzai、Naoki Miyata、Haruhiro Okuda

  DOI：10.1016/j.tetlet.2009.09.149

  日期：2009.12

  The reaction of ninhydrin with (+)-catechin in the presence of TMSOTf resulted in condensation product 1, which consists of a 2:1 mixture of epimers at the C-2 position. The antioxidative radical-scavenging activity of 1 against the galvinoxyl radical, acting as an oxyl radical, was significantly enhanced compared to (+)-catechin. Our results offer a new method for chemical modification of a natural phenolic antioxidant. (C) 2009 Elsevier Ltd. All rights reserved.