(E)-3-(3-methoxyl-4-hydroxyphenyl) amyl acrylate

• 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: (E)-3-(3-methoxyl-4-hydroxyphenyl) amyl acrylate
• 英文别名: pentyl ferulate；pentyl (E)-ferulate；pentyl (E)-3-(4-hydroxy-3-methoxyphenyl)acrylate；(E)-1-pentyl 3-(4-hydroxy-3-methoxyphenyl)acrylate；Pentylferulate；pentyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: YUDYTTRJOKXRFT-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  (E)-3-(3-methoxyl-4-hydroxyphenyl) amyl acrylate 、 阿司匹林 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以42%的产率得到(E)-2-acetoxyl benzoic acid [4-(3-pentyloxy-3-oxo-1-propenyl)-2-methoxyl]phenyl ester
  参考文献：
  名称：

  阿魏酸衍生物的设计、合成和体外抗血小板聚集活性

  摘要：

  为了发现具有抗血小板聚集活性的新化合物，设计并合成了一些阿魏酸（FA）衍生物。这些化合物的体外抗血小板聚集活性通过比浊试验进行评估。结果表明，目标化合物7f具有较强的抗血小板聚集活性，其IC50为27.6 μmol/L，7f可作为一种新型的有效抗血小板聚集候选物。

  DOI：

  10.1155/2015/376527
• 作为产物：
  描述：

  阿魏酸 、 戊醇 在 硫酸 作用下， 148.0 ℃ 、137.9 kPa 条件下， 反应 0.08h， 以93%的产率得到(E)-3-(3-methoxyl-4-hydroxyphenyl) amyl acrylate
  参考文献：
  名称：

  Highly Efficient Esterification of Ferulic Acid Under Microwave Irradiation

  摘要：

  描述了在微波辐射下高效合成阿魏酸烷基酯的方法。这些反应时间为3~5分钟，比传统的合成方法要短得多，并且以较高的收率获得了阿魏酸烷基酯。

  DOI：

  10.3390/molecules14062118

文献信息

• Highly Efficient Esterification of Ferulic Acid Under Microwave Irradiation
  作者：Nian-Guang Li、Zhi-Hao Shi、Yu-Ping Tang、Bao-Quan Li、Jin-Ao Duan

  DOI：10.3390/molecules14062118

  日期：——

  A highly efficient synthesis of alkyl ferulates under microwave irradiation is described. The time of these reactions ranged from 3 to 5 minutes, which was much shorter than the traditional synthetic methods, and the alkyl ferulates were obtained in higher yields.

  描述了在微波辐射下高效合成阿魏酸烷基酯的方法。这些反应时间为3~5分钟，比传统的合成方法要短得多，并且以较高的收率获得了阿魏酸烷基酯。
• 10.1016/j.fitote.2024.105988
  作者：Priya, Telukuntla Sai、Siva, Bandi、Vemireddy, Sravanthi、Babu, K. Suresh

  DOI：10.1016/j.fitote.2024.105988

  日期：——

  Traditional medicinal plants have been used for centuries for their immunomodulatory properties and therapeutic potentials. The present study aims to investigate the immunomodulatory constituents from traditional medicinal plant, (willd.). Our study resulted in the isolation of new compound, 27-hydroxy octacosyl ferulate () along with eleven known compounds (−). The structures of the isolated compounds

  传统药用植物因其免疫调节特性和治疗潜力而被使用了几个世纪。本研究旨在研究传统药用植物（willd.）的免疫调节成分。我们的研究结果分离出了新化合物 27-羟基二十八烷基阿魏酸酯 () 以及 11 种已知化合物 (−)。通过核磁共振（1D 和 2D）和质谱方法的结合对分离的化合物的结构进行了表征。化合物（阿魏酸）的半合成产生（和）衍生物。此外，通过评估分离的化合物和合成的衍生物对巨噬细胞（IL-6）和 DC 活化标记物（CD 11c 和 86）的细胞毒性和促炎作用，评估了其免疫调节潜力。生物学结果表明，粗提物显示出有效的免疫调节活性，而分离的化合物和合成类似物则显示出中等活性。在测试的化合物中，新化合物()、槲皮素()及其衍生物被发现无细胞毒性并显示出免疫调节潜力。因此，可以研究这些化合物的自身免疫和其他免疫抑制病症。
• Impact of Alkyl Esters of Caffeic and Ferulic Acids on Tumor Cell Proliferation, Cyclooxygenase Enzyme, and Lipid Peroxidation
  作者：Bolleddula Jayaprakasam、Mulabagal Vanisree、Yanjun Zhang、David L. Dewitt、Muraleedharan G. Nair

  DOI：10.1021/jf060899p

  日期：2006.7.1

  The antioxidant ferulic and caffeic acid phenolics are ubiquitous in plants and abundant in fruits and vegetables. We have synthesized a series of ferulic and caffeic acid esters and tested for tumor cell proliferation, cyclooxygenase enzymes (COX-1 and -2) and lipid peroxidation inhibitory activities in vitro. In the tumor cell proliferation assay, some of these esters showed excellent growth inhibition of colon cancer cells. Among the phenolics esters assayed, compounds 10 (C-12-caffeate), 11 (C-16-caffeate), 21 (C-8-ferulate), and 23 (C-12-ferulate) showed strong growth inhibition with IC50 values of 16.55, 13.46, 18.67, and 7.57 mu g/mL in a breast cancer cell line; 9.65, 7.45, 17.05, and 4.35 mu g/mL in a lung cancer cell line; 5.78, 3.5, 4.29, and 2.46 mu g/mL in a colon cancer cell line; 12.04, 12.21, 14.63, and 8.09 mu g/mL in a central nervous system cancer cell line; and 8.62, 7.76, 11.0, and 5.37 in a gastric cancer cell line. In COX enzyme inhibitory assays, ferulic and caffeic acid esters significantly inhibited both COX-1 and COX-2 enzymes. Caffeates 5-10 (C-4-C-12), inhibited COX-1 enzyme between 50% and 90% and COX-2 enzyme by about 70%, whereas ferulates 15-21 (C-3-C-8) inhibited COX-1 and COX-2 enzymes by 85-95% 25 mu g/mL. Long-chain caffeates 11-14 (C-16-C-22) and short-chain ferulates 15-20 (C-3-C-5) were the most active in lipid peroxidation inhibition and showed 6070% activity at 5 mu g/mL concentration.
• Design, Synthesis, and<i>In Vitro</i>Antiplatelet Aggregation Activities of Ferulic Acid Derivatives
  作者：Peng-Xuan Zhang、Hang Lin、Cheng Qu、Yu-Ping Tang、Nian-Guang Li、Jun Kai、Guanxiong Shang、Baoquan Li、Li Zhang、Hui Yan、Pei Liu、Jin-Ao Duan

  DOI：10.1155/2015/376527

  日期：——

  In order to discover new compounds with antiplatelet aggregation activities, some ferulic acid (FA) derivatives were designed and synthesized. The in vitro antiplatelet aggregation activities of these compounds were assessed by turbidimetric test. The results showed that the target compound 7f had potent antiplatelet aggregation activity with its IC50 27.6 μmol/L, and 7f can be regarded as a novel potent

  为了发现具有抗血小板聚集活性的新化合物，设计并合成了一些阿魏酸（FA）衍生物。这些化合物的体外抗血小板聚集活性通过比浊试验进行评估。结果表明，目标化合物7f具有较强的抗血小板聚集活性，其IC50为27.6 μmol/L，7f可作为一种新型的有效抗血小板聚集候选物。