(E)-((E)-3,7-dimethylocta-2,6-dienyl) 3-(3,4-dihydroxyphenyl)acrylate | 119644-20-1

• 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: (E)-((E)-3,7-dimethylocta-2,6-dienyl) 3-(3,4-dihydroxyphenyl)acrylate
• 英文别名: 3,7-dimethyl-2,6-octadienyl caffeic acid ester；geranyl caffeate；[(2E)-3,7-dimethylocta-2,6-dienyl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• CAS: 119644-20-1
• 化学式: C₁₉H₂₄O₄
• 分子量: 316.397
• InChiKey: ORKOCTJFEOMBGA-WSZGUFMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  香叶醇 、 TRANS-咖啡酸 在 氯化亚砜 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以14%的产率得到(E)-((E)-3,7-dimethylocta-2,6-dienyl) 3-(3,4-dihydroxyphenyl)acrylate
  参考文献：
  名称：

  Inhibitory effect of the alkyl side chain of caffeic acid analogues on lipopolysaccharide-induced nitric oxide production in RAW264.7 macrophages

  摘要：

  Caffeic acid esters, one of the components of propolis, are known to show a variety of biological effects such as anti-tumor, anti-oxidant, and anti-inflammatory activities. Although, the anti-inflammatory activities of caffeic acid esters have been studied by analyzing their structure, the detailed mechanisms of their activities remain unclear. Thus, in this study, we examined the function of the ester functional group and the alkyl side chain (alcoholic part) and transformed caffeic acid to several derivatives. The inhibitory effect of these derivatives on NO production in murine macrophage RAW264.7 cells was dependent on the length and size of the alkyl moiety, and undecyl caffeate was the most potent inhibitor of NO production. In addition, individual experiments using undecanol, caffeic acid, undecanol plus caffeic acid, and undecyl caffeate showed that the connection between caffeic acid and the alkyl chain is critical for activity. Amide and ketone derivatives showed that not only the ester functional group but also the amide and ketone functional groups exhibit an inhibitory effect on NO production. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.07.006