trans-2-nonen-1-yl 3,4-dihydroxybenzoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: trans-2-nonen-1-yl 3,4-dihydroxybenzoate
• 英文别名: [(E)-non-2-enyl] 3,4-dihydroxybenzoate
• 化学式: C₁₆H₂₂O₄
• 分子量: 278.348
• InChiKey: PBEBHODSCJDNIT-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  原儿茶酸 、 反-2-壬烯-1-醇 在 N,N'-二环己基碳二亚胺 作用下， 生成 trans-2-nonen-1-yl 3,4-dihydroxybenzoate
  参考文献：
  名称：

  抗菌剂的合理设计：烷基（烯）基二羟基苯甲酸酯和二羟基苯基链烷酸酯的抗真菌活性。

  摘要：

  每个3,4-和3,5-二羟基苯甲酸烷基酯和3,4-和3,5-二羟基苯基链烷酸烷基酯的同源系列（C3-C14）对啤酒酵母具有相似的抗真菌活性。它们的壬基衍生物对这种酵母表现出最有效的抗真菌活性，其最小杀真菌浓度（MFC）在12.5至50微克/毫升之间。此外，合成了具有不同侧链的各种3,4-二羟基苯甲酸酯，即不饱和，支链和脂环族，并比较了它们的活性。

  DOI：

  10.1016/j.bmcl.2003.08.057

文献信息

• Rational design of antimicrobial agents: antifungal activity of alk(en)yl dihydroxybenzoates and dihydroxyphenyl alkanoates
  作者：Ken-ichi Nihei、Atsuko Nihei、Isao Kubo

  DOI：10.1016/j.bmcl.2003.08.057

  日期：2003.11

  similar antifungal activity against Saccharomyces cerevisiae. Their nonyl derivatives exhibit the most potent antifungal activity against this yeast with the minimum fungicidal concentration (MFC) in the range between 12.5 and 50 microg/mL. In addition, various 3,4-dihydroxybenzoates, possessing different side chains, namely unsaturated, branched and alicyclic were synthesized and their activity was compared

  每个3,4-和3,5-二羟基苯甲酸烷基酯和3,4-和3,5-二羟基苯基链烷酸烷基酯的同源系列（C3-C14）对啤酒酵母具有相似的抗真菌活性。它们的壬基衍生物对这种酵母表现出最有效的抗真菌活性，其最小杀真菌浓度（MFC）在12.5至50微克/毫升之间。此外，合成了具有不同侧链的各种3,4-二羟基苯甲酸酯，即不饱和，支链和脂环族，并比较了它们的活性。
• Molecular design of multifunctional antibacterial agents against methicillin resistant Staphylococcus aureus (MRSA)
  作者：I Kubo

  DOI：10.1016/s0968-0896(03)00433-4

  日期：2003.9.15

  Antibacterial activity of a series of alkyl gallates (3,4,5-trihydroxybenzoates) against Gram-positive bacteria, especially methicillin resistant Staphylococcus aureus (MRSA) strains was evaluated. Gram-positive bacteria are all susceptible to alkyl gallates. Dodecyl gallate was the most effective against MRSA ATCC 33591 strain with the minimum bactericidal concentration (MBC) of 25 mug/mL (74 muM). The time-kill curve study showed that dodecyl gallate was bactericidal against this MRSA strain at any growth stage. This activity was observed even in the chloramphenicol-treated cells, but the rate of decrease of cell number was slower than that in the exponentially growing cells. The bactericidal activity of medium-chain alkyl gallates was noted in combination with their ability to disrupt the native membrane-associated function nonspecifically as surface-active agents (surfactants) and to inhibit the respiratory electron transport. Subsequently, the same series of alkyl protocatechuates (3,4-dihydroxybenzoates) were studied and the results obtained are similar to those found for alkyl gallates. The length of the alkyl chain is not a major contributor but is related to the activity. (C) 2003 Elsevier Ltd. All rights reserved.