hexadecyl ferulate

• 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: hexadecyl ferulate
• 英文别名: palmityl ferulate；Hexadecyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• 化学式: C₂₆H₄₂O₄
• 分子量: 418.617
• InChiKey: ZISDTRGMDDVTKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  30
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 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 、 1-十六烷醇 在 Novozym 435 作用下， 80.0 ℃ 、80.0 kPa 条件下， 反应 72.0h， 生成 hexadecyl ferulate
  参考文献：
  名称：

  Solvent-free Lipase-Catalyzed Preparation of Long-Chain Alkyl Phenylpropanoates and Phenylpropyl Alkanoates

  摘要：

  An enzymatic method was developed for the preparation of medium- or long-chain alkyl 3-phenylpropenoates (alkyl cinnamates), particularly alkyl hydroxy- and methoxy-substituted cinnamates such as oleyl p-coumarate and oleyl ferulate. The various alkyl cinnamates were formed in high to moderate yield by lipase-catalyzed esterification of cinnamic acid and its analogues with fatty alcohols in vacuo at moderate temperatures in the absence of drying agents and solvents. Immobilized Candida antarctica lipase B was the most effective biocatalyst for the various esterification reactions. The relative esterification activities were of the following order: clihydrocinnamic > cinnamic > 3-methoxycinnamic > dihydrocaffeic approximate to 3-hydroxycinnamic > 4-methoxycinnamic > 2-methoxycinnamic > 4-hydroxycinnamic > ferulic approximate to 3,4-dimethoxycinnamic > 2-hydroxycinnamic acid. With respect to the position of the substituents at the phenyl moiety, the esterification activity increased in the order meta > para > ortho. Rhizomucor miehei lipase demonstrated moderate esterification activity. Compounds with inverse chemical structure, that is, 3-phenylpropyl alkanoates such as 3-(4-hydroxyphenyl)propyl oleate, were also obtained in high yield by esterification of fatty acids with the corresponding 3-phenylpropan-1-ols.

  DOI：

  10.1021/jf060052t

文献信息

• Evaluation of the antimicrobial and antioxidant properties of synthetic phenolipids
  作者：Horiya Nassiba Ham、Matthieu M. Mention、Blandine Godon、Fanny Brunissen、Manon Thomas、Florent Allais、Michel Lopez、Nabila Imatoukene

  DOI：10.1016/j.procbio.2024.03.015

  日期：2024.6

  of phenolic compounds by lipophilization allowing the synthesis of new compounds with improved biological properties. This study aims to investigate the antimicrobial effects of eight synthesized phenolipids, derived from bioactive coumaric and ferulic acid esters, against , , and . Antioxidant activity, as well as antimicrobial capacity were evaluated through DPPH assays and classical disc agar diffusion

  通过亲脂化对酚类化合物进行官能化，从而可以合成具有改善的生物特性的新化合物。本研究旨在研究源自生物活性香豆酸酯和阿魏酸酯的八种合成酚脂对 、 、 和 的抗菌作用。分别通过 DPPH 测定和经典圆盘琼脂扩散评估抗氧化活性以及抗菌能力，同时使用流式细胞术测定评估细胞活力。抗氧化活性结果表明阿魏酸酯比香豆酸酯表现出更高的抗自由基活性。琼脂扩散测定结果表明，1-甲基丙基香豆酸酯和 1-甲基丙基阿魏酸酯 (1-MPF) 对所有测试的微生物均具有有效的抗菌活性，最低抑制浓度 (MIC) 值在 0.9 至 3.5 mM 之间。此外，流式细胞术显示 1-MPF 和香豆酸癸酯表现出显着的杀菌活性 (p < 0.05)，几乎有 63% 的细胞死亡。与常用的琼脂方法相比，流式细胞术被证明是一种快速、直接的分析工具，可以评估抗菌活性，同时提供抑制类型的信息。这些结果表明酚脂作为有效的亲脂性生物活性分子可用于保护食
• 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.