ferulic acid (2-ethylhexyl) ester

• 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: ferulic acid (2-ethylhexyl) ester
• 英文别名: 2-ethylhexyl ferulate；2-Ethylhexyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• 化学式: C₁₈H₂₆O₄
• 分子量: 306.402
• InChiKey: VFRQPMMHAPIZIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  三乙酰基没食子酰氯 、 ferulic acid (2-ethylhexyl) ester 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以81%的产率得到2-ethyl-1-hexyl 3-[4-(3,4,5-triacetyloxybenzoyloxy)-3-methoxyphenyl]-2-propenoate
  参考文献：
  名称：

  Synthesis of Novel Polyphenols Consisted of Ferulic and Gallic Acids, and Their Inhibitory Effects on Phorbol Ester-Induced Epstein–Barr Virus Activation and Superoxide Generation

  摘要：

  We prepared novel polyphenols which were esters composed of two naturally occurring products, ferulic and gallic acids, and investigated their inhibitory effects on 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced Epstein-Barr virus (EBV) activation and superoxide (O-2(-)) generation. Most of these compounds exhibited significant EBV activation suppression at a concentration of 20 muM and in particular, the ester 5f having 2-metyl-1-butyl group showed high activity. The suppressive effects on O-2(-) generation were also observed in most of the esters. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00361-3
• 作为产物：
  描述：

  阿魏酸 、 2-乙基己醇 在 Novozym435 作用下， 以 neat (no solvent) 为溶剂， 78.0 ℃ 、74.66 kPa 条件下， 反应 24.0h， 生成 ferulic acid (2-ethylhexyl) ester
  参考文献：
  名称：

  新型亲脂抗氧化剂的高效合成：阿魏酸2-乙基己基酯。

  摘要：

  酯形式的阿魏酸在改善某些病理状况和抑制脂质氧化方面显示出较强的能力。在本研究中，开发了一种无溶剂减压蒸发系统，用于脂肪酶催化从阿魏酸和2-乙基己醇合成2-乙基己基阿魏酸酯（2-EF）。选择具有响应面方法（RSM）和人工神经网络（ANN）的Box-Behnken设计来对过程进行建模和优化。基于2-EF的收率，反应温度是所有变量中摩尔转化率最重要的工艺因素。根据设计数据计算出的残差值和确定系数（R²）表明，在数据拟合中，ANN优于RSM。总体，目前，在低压蒸发系统中，在低反应温度下，脂肪酶催化的2-EF合成方法显示出较高的2-EF生产效率。值得注意的是，这种方法可以减少通常在高温下长期生物合成过程中发生的酶变性和阿魏酸氧化。

  DOI：

  10.3390/molecules21040478

文献信息

• METHOD FOR PRODUCING CINNAMIC ACID ESTER COMPOUND
  申请人：TOHOKU UNIVERSITY

  公开号：US20200123094A1

  公开（公告）日：2020-04-23

  A method for producing a cinnamic acid ester derivative includes reacting a cinnamic acid derivative compound represented by the formula (1), wherein the symbols are as defined in the description, with an alcohol compound represented by the formula: R 6 OH, wherein the symbol is as defined in the description, in the presence of a strong acid resin catalyst without using a solvent. As the cinnamic acid derivative compound, cinnamic acid, ferulic acid, and caffeic acid are preferred, and as the alcohol compound, methanol, ethanol, propanol, butanol, pentanol, hexanol, ethylene glycol, glycerol, phenethyl alcohol, and a monosaccharide are preferred.

  一种制备肉桂酸酯衍生物的方法，包括在无溶剂的情况下，将由公式（1）表示的肉桂酸衍生物化合物（其中符号如说明中所定义）与由公式R6OH表示的醇化合物（其中符号如说明中所定义）在强酸树脂催化剂的存在下反应。作为肉桂酸衍生物化合物，优选肉桂酸、阿魏酸和咖啡酸，作为醇化合物，优选甲醇、乙醇、丙醇、丁醇、戊醇、己醇、乙二醇、甘油、苯乙醇和单糖。
• Solvent-free Lipase-Catalyzed Preparation of Long-Chain Alkyl Phenylpropanoates and Phenylpropyl Alkanoates
  作者：Klaus Vosmann、Petra Weitkamp、Nikolaus Weber

  DOI：10.1021/jf060052t

  日期：2006.4.1

  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.