3,4-dihydroxycinnamic acid n-undecyl ester

• 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: 3,4-dihydroxycinnamic acid n-undecyl ester
• 英文别名: Daphnecinnamte B；Caffeic acid undecyl ester；undecyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• 化学式: C₂₀H₃₀O₄
• 分子量: 334.456
• InChiKey: DIAOJQJAZSZGDC-WYMLVPIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  24
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 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：

  十一烷醇 、 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23%的产率得到3,4-dihydroxycinnamic acid n-undecyl ester
  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

文献信息

• [EN] CAFFEIC ACID DERIVATIVES AND USES THEREOF<br/>[FR] DÉRIVÉS D'ACIDE CAFÉIQUE ET LEURS UTILISATIONS
  申请人：MUSC FOUND FOR RES DEV

  公开号：WO2017161093A1

  公开（公告）日：2017-09-21

  The present invention relates to compounds of formula (I): including any stereochemically isomeric form thereof, or pharmaceutically acceptable salts thereof, for the treatment of tuberculosis.

  本发明涉及公式(I)的化合物，包括其任何立体化异构体，或其药用可接受的盐，用于治疗结核病。
• Inhibitory effect of the alkyl side chain of caffeic acid analogues on lipopolysaccharide-induced nitric oxide production in RAW264.7 macrophages
  作者：Koji Uwai、Yuu Osanai、Takuma Imaizumi、Syu-ichi Kanno、Mitsuhiro Takeshita、Masaaki Ishikawa

  DOI：10.1016/j.bmc.2008.07.006

  日期：2008.8

  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.