vinyl ferulate | 938433-11-5

• 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: vinyl ferulate
• 英文别名: Ethenyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate；ethenyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• CAS: 938433-11-5
• 化学式: C₁₂H₁₂O₄
• 分子量: 220.225
• InChiKey: NXTSIKLGYGRCLU-UHFFFAOYSA-N

物化性质

• 沸点：
  350.0±32.0 °C(Predicted)
• 密度：
  1.194±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  vinyl ferulate 在 水 作用下， 生成 阿魏酸
  参考文献：
  名称：

  Optimized synthesis of novel prenyl ferulate performed by feruloyl esterases from Myceliophthora thermophila in microemulsions

  摘要：

  Five feruloyl esterases (FAEs; EC 3.1.1.73), FaeA1, FaeA2, FaeB1, and FaeB2 from Myceliophthora thermophila C1 and MtFae1a from M. thermophila ATCC 42464, were tested for their ability to catalyze the transesterification of vinyl ferulate (VFA) with prenol in detergentless microemulsions. Reaction conditions were optimized investigating parameters such as the medium composition, the substrate concentration, the enzyme load, the pH, the temperature, and agitation. FaeB2 offered the highest transesterification yield (71.5 +/- 0.2%) after 24 h of incubation at 30 A degrees C using 60 mM VFA, 1 M prenol, and 0.02 mg FAE/mL in a mixture comprising of 53.4:43.4:3.2 v/v/v n-hexane:t-butanol:100 mM MOPS-NaOH, pH 6.0. At these conditions, the competitive side hydrolysis of VFA was 4.7-fold minimized. The ability of prenyl ferulate (PFA) and its corresponding ferulic acid (FA) to scavenge 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals was significant and similar (IC50 423.39 mu M for PFA, 329.9 mu M for FA). PFA was not cytotoxic at 0.8-100 mu M (IC50 220.23 mu M) and reduced intracellular reactive oxygen species (ROS) in human skin fibroblasts at concentrations ranging between 4 and 20 mu M as determined with the dichloro-dihydro-fluorescein diacetate (DCFH-DA) assay.

  DOI：

  10.1007/s00253-017-8089-8
• 作为产物：
  描述：

  乙酸乙烯酯 、 阿魏酸 在 mercury(II) diacetate 、 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 以68%的产率得到vinyl ferulate
  参考文献：
  名称：

  脂酶介导的酚酸乙烯基酯及其类似物对甲基α-d-吡喃葡萄糖苷的酰化反应中的供体特异性和区域选择性

  摘要：

  使用固定化的脂酶将几种模型酚和非酚乙烯基酯酰化作为模型受体的甲基α- d-吡喃葡萄糖苷。研究了供体特异性和反应的区域选择性。结构上不同的供体的转化率和酰化速率表明，Lipolase的合成反应性对应于A型阿魏酸酯酶的水解活性。Lipolase对甲基α- d-吡喃葡萄糖苷的主要位置表现出显着的区域选择性。当酚酸的乙烯基酯（羟基苯甲酸酯，羟基苯基链烷酸酯和羟基肉桂酸酯）用作酰基供体时，酰化作用仅发生在6- O主位置。除了主要的6- O-酰基产品（52–79％）外，2,6-二-使用非酚供体时，从反应混合物中分离出O-酰化衍生物（2-13％）（酚酸的完全甲氧基化衍生物的乙烯基酯，以及苯甲酸乙烯酯，肉桂酸酯或某些杂环类似物）。

  DOI：

  10.1016/j.bmcl.2013.07.051

文献信息

• 一种阿魏酸衍生物及其应用
  申请人：刘策

  公开号：CN108191629B

  公开（公告）日：2020-12-29

  本发明公开一种阿魏酸衍生物及其应用，所述阿魏酸衍生物包括：4‑(4‑羟基‑3‑甲氧苯基)‑3‑丁烯‑2‑酮、4‑羟基‑3‑甲氧基肉桂酸乙烯酯、3‑(4‑羟基‑3‑甲氧基苯基)‑N‑(4‑甲氧基苯基)丙烯酰胺、N‑(4‑氟苯基)‑3‑(4‑羟基‑3‑甲氧基苯基)丙烯酰胺。其具有很高的抑制杂草生长和杀灭去除杂草的活性，属于微生物次生代谢产物结构改造应用于农业植物保护领域，对反枝苋、稗草、马唐、狗尾草、油菜等均有一定的抑制效果，可广泛应用于农业生产中，为一种新型的除草剂活性成分，具有制备方法简单、合成原料易得、安全环保、对非靶标作物无害等优点。
• Glycerol acyl-transfer kinetics of a circular permutated Candida antarctica lipase B
  作者：Joseph A. Laszlo、Ying Yu、Stefan Lutz、David L. Compton

  DOI：10.1016/j.molcatb.2011.06.002

  日期：2011.11

  Triacylglycerols containing a high abundance of unusual fatty acids, such as gamma-linolenic acid, or novel arylaliphatic acids, such as ferulic acid, are useful in pharmaceutical and cosmeceutical applications. Candida antarctica lipase B (CALB) is quite often used for non-aqueous synthesis, although the wildtype enzyme can be rather slow with bulky and sterically hindered acyl donor substrates. The catalytic performance of a circularly permutated variant of CALB, cp283, with various acyl donors and glycerol was examined. In comparison to wild-type CALB, butyl oleate and ethyl gamma-linolenate glycerolysis rates were 2.2- and 4.0-fold greater, respectively. Cp283 showed substrate inhibition by glycerol, which was not the case with the wild-type version. With either ethyl ferulate or vinyl ferulate acyl donors, cp283 matched the performance of wild-type CALB. Changes in active site accessibility resulting from circular permutation led to increased catalytic rates for bulky fatty acid esters but did not overcome the steric hindrance or energetic limitations experienced by arylaliphatic esters. Published by Elsevier B.V.
• Donor specificity and regioselectivity in Lipolase mediated acylations of methyl α-d-glucopyranoside by vinyl esters of phenolic acids and their analogues
  作者：Mária Mastihubová、Vladimír Mastihuba

  DOI：10.1016/j.bmcl.2013.07.051

  日期：2013.10

  Methyl α-d-glucopyranoside as a model acceptor was acylated by several phenolic and non-phenolic vinyl esters using immobilised Lipolase. Donor specificity and regioselectivity of reaction were investigated. Conversion and rate of acylation by structurally varied donors indicates that the synthetic reactivity of Lipolase corresponds to the hydrolytic activity of feruloyl esterase type A. Lipolase exhibited

  使用固定化的脂酶将几种模型酚和非酚乙烯基酯酰化作为模型受体的甲基α- d-吡喃葡萄糖苷。研究了供体特异性和反应的区域选择性。结构上不同的供体的转化率和酰化速率表明，Lipolase的合成反应性对应于A型阿魏酸酯酶的水解活性。Lipolase对甲基α- d-吡喃葡萄糖苷的主要位置表现出显着的区域选择性。当酚酸的乙烯基酯（羟基苯甲酸酯，羟基苯基链烷酸酯和羟基肉桂酸酯）用作酰基供体时，酰化作用仅发生在6- O主位置。除了主要的6- O-酰基产品（52–79％）外，2,6-二-使用非酚供体时，从反应混合物中分离出O-酰化衍生物（2-13％）（酚酸的完全甲氧基化衍生物的乙烯基酯，以及苯甲酸乙烯酯，肉桂酸酯或某些杂环类似物）。
• Optimized synthesis of novel prenyl ferulate performed by feruloyl esterases from Myceliophthora thermophila in microemulsions
  作者：Io Antonopoulou、Laura Leonov、Peter Jütten、Gabriella Cerullo、Vincenza Faraco、Adamantia Papadopoulou、Dimitris Kletsas、Marianna Ralli、Ulrika Rova、Paul Christakopoulos

  DOI：10.1007/s00253-017-8089-8

  日期：2017.4

  Five feruloyl esterases (FAEs; EC 3.1.1.73), FaeA1, FaeA2, FaeB1, and FaeB2 from Myceliophthora thermophila C1 and MtFae1a from M. thermophila ATCC 42464, were tested for their ability to catalyze the transesterification of vinyl ferulate (VFA) with prenol in detergentless microemulsions. Reaction conditions were optimized investigating parameters such as the medium composition, the substrate concentration, the enzyme load, the pH, the temperature, and agitation. FaeB2 offered the highest transesterification yield (71.5 +/- 0.2%) after 24 h of incubation at 30 A degrees C using 60 mM VFA, 1 M prenol, and 0.02 mg FAE/mL in a mixture comprising of 53.4:43.4:3.2 v/v/v n-hexane:t-butanol:100 mM MOPS-NaOH, pH 6.0. At these conditions, the competitive side hydrolysis of VFA was 4.7-fold minimized. The ability of prenyl ferulate (PFA) and its corresponding ferulic acid (FA) to scavenge 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals was significant and similar (IC50 423.39 mu M for PFA, 329.9 mu M for FA). PFA was not cytotoxic at 0.8-100 mu M (IC50 220.23 mu M) and reduced intracellular reactive oxygen species (ROS) in human skin fibroblasts at concentrations ranging between 4 and 20 mu M as determined with the dichloro-dihydro-fluorescein diacetate (DCFH-DA) assay.