oleyl caffeate

• 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: oleyl caffeate
• 英文别名: [(Z)-octadec-9-enyl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• 化学式: C₂₇H₄₂O₄
• 分子量: 430.628
• InChiKey: WTABFZAGEIYEES-YSBCPJPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  31
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 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：

  TRANS-咖啡酸 在 哌啶 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 oleyl caffeate
  参考文献：
  名称：

  受自然产物启发的阿魏酸和咖啡酸的酯和酰胺，作为HIV-1逆转录酶的双重抑制剂。

  摘要：

  使用HIV-1逆转录酶（RT）相关的RNase H抑制试验作为先导，乌头叶的二氯甲烷提取物的生物引导分级分离导致分离出5个三萜（1-5）和3个3-甲氧基-4 -羟基苯基衍生物（6-8）。该分离物的结构通过1D和2D NMR实验以及ESI-MS确定。阿魏十四酸（8）显示出有趣的RNase H IC50值为12.4μM，并且由于该次生代谢产物的合成可及性，因此进行了结构-活性关系研究。合成了一系列阿魏酸和咖啡酸的酯和酰胺，其中最活跃的是N-油基咖啡酰胺，对RT相关功能，核糖核酸酶H和DNA聚合酶均显示出强大的抑制活性。

  DOI：

  10.1016/j.ejmech.2017.02.054

文献信息

• Highly Efficient Preparation of Lipophilic Hydroxycinnamates by Solvent-free Lipase-Catalyzed Transesterification
  作者：Petra Weitkamp、Klaus Vosmann、Nikolaus Weber

  DOI：10.1021/jf0611973

  日期：2006.9.1

  Various medium- or long-chain alkyl cinnamates and hydroxycinnamates, including oleyl p-coumarate as well as palmityl and oleyl ferulates, were prepared in high yield by lipase-catalyzed transesterification of an equimolar mixture of a short-chain alkyl cinnamate and a fatty alcohol such as lauryl, palmityl, and oleyl alcohol under partial vacuum at moderate temperature in the absence of solvents and drying agents in direct contact with the reaction mixture. Immobilized lipase B from Candida antarctica was the most effective biocatalyst for the various transesterification reactions. Transesterification activity of this enzyme was up to 56-fold higher than esterification activity for the preparation of medium- and long-chain alkyl ferulates. The relative transesterification activities found for C. antarctica lipase were of the following order: hydrocinnamate > cinnamate > 4- hydroxyhydrocinnamate > 3-methoxycinnamate > 2-methoxycinnamate approximate to 4-methoxycinnamate approximate to 3-hydroxycinnamate > hydrocaffeate approximate to 4-hydroxycinnamate > ferulate > 2-hydroxycinnamate > caffeate approximate to sinapate. With respect to the position of the hydroxy substituents at the phenyl moiety, the transesterification activity of C. antarctica lipase B increased in the order meta > para > ortho. The immobilized lipases from Rhizomucor miehei and Thermomyces lanuginosus demonstrated moderate and low transesterification activity, respectively. Compounds with inverse chemical structure, that is, 3-phenylpropyl alkanoates such as 3-(4-hydroxyphenyl) propyl oleate and 3-(3,4- dimethoxyphenyl) propyl oleate, were obtained by C. antarctica lipase-catalyzed transesterification of fatty acid methyl esters with the corresponding 3- phenylpropan-1-ols in high yield, as well.
• Natural product-inspired esters and amides of ferulic and caffeic acid as dual inhibitors of HIV-1 reverse transcriptase
  作者：Vijay P. Sonar、Angela Corona、Simona Distinto、Elias Maccioni、Rita Meleddu、Benedetta Fois、Costantino Floris、Nilesh V. Malpure、Stefano Alcaro、Enzo Tramontano、Filippo Cottiglia

  DOI：10.1016/j.ejmech.2017.02.054

  日期：2017.4

  Using an HIV-1 Reverse Transcriptase (RT)-associated RNase H inhibition assay as lead, bioguided fractionation of the dichloromethane extract of the Ocimum sanctum leaves led to the isolation of five triterpenes (1-5) along with three 3-methoxy-4-hydroxy phenyl derivatives (6-8). The structure of this isolates were determined by 1D and 2D NMR experiments as well as ESI-MS. Tetradecyl ferulate (8) showed

  使用HIV-1逆转录酶（RT）相关的RNase H抑制试验作为先导，乌头叶的二氯甲烷提取物的生物引导分级分离导致分离出5个三萜（1-5）和3个3-甲氧基-4 -羟基苯基衍生物（6-8）。该分离物的结构通过1D和2D NMR实验以及ESI-MS确定。阿魏十四酸（8）显示出有趣的RNase H IC50值为12.4μM，并且由于该次生代谢产物的合成可及性，因此进行了结构-活性关系研究。合成了一系列阿魏酸和咖啡酸的酯和酰胺，其中最活跃的是N-油基咖啡酰胺，对RT相关功能，核糖核酸酶H和DNA聚合酶均显示出强大的抑制活性。