octadecyl ferulate | 133882-77-6

• 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: octadecyl ferulate
• 英文别名: n-C18 Wachs-Alkohol-ferulat；2-Propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-, octadecyl ester；octadecyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• CAS: 133882-77-6；133882-78-7；64190-81-4
• 化学式: C₂₈H₄₆O₄
• 分子量: 446.671
• InChiKey: SESLBPIXVOYQJJ-UHFFFAOYSA-N

物化性质

• 熔点：
  86-89 °C
• 沸点：
  552.3±35.0 °C(Predicted)
• 密度：
  0.985±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.7
• 重原子数：
  32
• 可旋转键数：
  21
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 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：

  硬脂醇 、 阿魏酸 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以42.2%的产率得到octadecyl ferulate
  参考文献：
  名称：

  Octadecyl ferulate behavior in 1,2-Dioleoylphosphocholine liposomes

  摘要：

  Octadecyl ferulate was prepared using solid acid catalyst, monitored using Supercritical Fluid Chromatography and purified to a 42% yield. Differential scanning calorimetry measurements determined octadecyl ferulate to have melting/solidification phase transitions at 67 and 39 degrees C, respectively. AFM imaging shows that 5-mol% present in a lipid bilayer induced domains to form. Phase behavior measurements confirmed that octadecyl ferulate increased transition temperature of phospholipids. Fluorescence measurements demonstrated that octadecyl ferulate stabilized liposomes against leakage, maintained antioxidant capacity within liposomes, and oriented such that the feruloyl moiety remained in the hydrophilic region of the bilayer. Molecular modeling calculation indicated that antioxidant activity was mostly influenced by interactions within the bilayer. Published by Elsevier B.V.

  DOI：

  10.1016/j.saa.2015.08.009

文献信息

• Antioxidant Properties and Efficacies of Synthesized Alkyl Caffeates, Ferulates, and Coumarates
  作者：Ann-Dorit Moltke Sørensen、Erwann Durand、Mickaël Laguerre、Christelle Bayrasy、Jérôme Lecomte、Pierre Villeneuve、Charlotte Jacobsen

  DOI：10.1021/jf500588s

  日期：2014.12.31

  Caffeic, ferulic, and coumaric acids were lipophilized with saturated fatty alcohols (C1-C20). The antioxidant properties of these hydroxycinnamic acids and their alkyl esters were evaluated in various assays. Furthermore, the antioxidant efficiency of the compounds was evaluated in a simple o/w microemulsion using the conjugated autoxidizable triene (CAT) assay. All evaluated phenolipids had radical scavenging, reducing power, and metal chelating properties. Only caffeic acid and caffeates were able to form a complex with iron via their catechol group in the phenolic ring. In the o/w emulsion, the medium chain phenolipids of the three homologues series were most efficient. The antioxidant properties and efficacies were dependent upon functional groups substituted to the ring structure and were in the following order: caffeic acid and caffeates > ferulic acid and ferulates > coumaric acid and coumarates. Moreover, the results demonstrated that the test system has an impact on the antioxidative properties measured.
• Octadecyl ferulate behavior in 1,2-Dioleoylphosphocholine liposomes
  作者：Kervin O. Evans、David L. Compton、Nathan A. Whitman、Joseph A. Laszlo、Michael Appell、Karl E. Vermillion、Sanghoon Kim

  DOI：10.1016/j.saa.2015.08.009

  日期：2016.1

  Octadecyl ferulate was prepared using solid acid catalyst, monitored using Supercritical Fluid Chromatography and purified to a 42% yield. Differential scanning calorimetry measurements determined octadecyl ferulate to have melting/solidification phase transitions at 67 and 39 degrees C, respectively. AFM imaging shows that 5-mol% present in a lipid bilayer induced domains to form. Phase behavior measurements confirmed that octadecyl ferulate increased transition temperature of phospholipids. Fluorescence measurements demonstrated that octadecyl ferulate stabilized liposomes against leakage, maintained antioxidant capacity within liposomes, and oriented such that the feruloyl moiety remained in the hydrophilic region of the bilayer. Molecular modeling calculation indicated that antioxidant activity was mostly influenced by interactions within the bilayer. Published by Elsevier B.V.