hexyl 3-(4-hydroxy-3-methoxyphenyl)propanoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: hexyl 3-(4-hydroxy-3-methoxyphenyl)propanoate
• 英文别名: hexylhydroferulate；Dihydroferulic acid hexyl ester
• 化学式: C₁₆H₂₄O₄
• 分子量: 280.364
• InChiKey: DDXFRGUQKYLGNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  阿魏酸 在 palladium dichloride 盐酸 、 sodium hydroxide 作用下， 反应 12.0h， 生成 hexyl 3-(4-hydroxy-3-methoxyphenyl)propanoate
  参考文献：
  名称：

  Fungicidal Activities of Dihydroferulic Acid Alkyl Ester Analogues

  摘要：

  The natural product dihydroferulic acid (DFA, 1) and the synthesized DFA methyl (4a), ethyl (4b), propyl (4c), hexyl (4d), octyl (4e), and decyl (4f) esters were examined for antifungal activity. Test fungi included Saccharomyces cerevisiae (wild type, and deletion mutants slt2 Delta and bck1 Delta), Aspergillus fumigatus, and A. flavus. Growth inhibition of S. cerevisiae treated with 5 mM DFA or the corresponding esters was 4a, 4b, and 4c > 98%; 4d 18.8%; 1 6.4%; 4e 6.2%; and 4f 2.8%, relative to the control. The 50% minimum inhibitory concentrations for the more active propyl, methyl, and ethyl esters were 1.5, 2.1, and 4.0 mM, respectively. Compound 4c inhibited 100% growth of both aspergilli at 6.4 mM.

  DOI：

  10.1021/np0606345

文献信息

• Lipophilic phenolic antioxidants: Correlation between antioxidant profile, partition coefficients and redox properties
  作者：Fernanda M.F. Roleira、Christophe Siquet、Elizabeta Orrù、E. Manuela Garrido、Jorge Garrido、Nuno Milhazes、Gianni Podda、Fátima Paiva-Martins、Salette Reis、Rui A. Carvalho、Elisiário J. Tavares da Silva、Fernanda Borges

  DOI：10.1016/j.bmc.2010.06.090

  日期：2010.8

  Lipophilic compounds structurally based on caffeic, hydrocaffeic, ferulic and hydroferulic acids were synthesized. Subsequently, their antioxidant activity was evaluated as well as their partition coefficients and redox potentials. The structure-property-activity relationship (SPAR) results revealed the existence of a clear correlation between the redox potentials and the antioxidant activity. In addition, some compounds showed a proper lipophilicity to cross the blood-brain barrier. Their predicted ADME properties are also in accordance with the general requirements for potential CNS drugs. Accordingly, one can propose these phenolic compounds as potential antioxidants for tackling the oxidative status linked to the neurodegenerative processes. (C) 2010 Elsevier Ltd. All rights reserved.
• Fungicidal Activities of Dihydroferulic Acid Alkyl Ester Analogues
  作者：John J. Beck、Jong H. Kim、Bruce C. Campbell、Shen-Chieh Chou

  DOI：10.1021/np0606345

  日期：2007.5.25

  The natural product dihydroferulic acid (DFA, 1) and the synthesized DFA methyl (4a), ethyl (4b), propyl (4c), hexyl (4d), octyl (4e), and decyl (4f) esters were examined for antifungal activity. Test fungi included Saccharomyces cerevisiae (wild type, and deletion mutants slt2 Delta and bck1 Delta), Aspergillus fumigatus, and A. flavus. Growth inhibition of S. cerevisiae treated with 5 mM DFA or the corresponding esters was 4a, 4b, and 4c > 98%; 4d 18.8%; 1 6.4%; 4e 6.2%; and 4f 2.8%, relative to the control. The 50% minimum inhibitory concentrations for the more active propyl, methyl, and ethyl esters were 1.5, 2.1, and 4.0 mM, respectively. Compound 4c inhibited 100% growth of both aspergilli at 6.4 mM.