propyl ferulate | 59831-93-5

• 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: propyl ferulate
• 英文别名: ferulic acid propyl ester；n-propyl 4-hydroxy-3-methoxycinnamate；ferulic acid n-propyl ester；Propyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• CAS: 59831-93-5
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: XTSFEXUEVQUSQE-UHFFFAOYSA-N

物化性质

• 沸点：
  364.5±27.0 °C(Predicted)
• 密度：
  1.147±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  propyl ferulate 在 potassium carbonate 作用下， 以 乙腈 、 丁酮 为溶剂， 反应 4.5h， 生成
  参考文献：
  名称：

  Synthesis of Novel Antiviral Ferulic Acid–Eugenol and Isoeugenol Hybrids Using Various Link Reactions

  摘要：

  DOI：

  10.1021/acs.jafc.1c05521
• 作为产物：
  描述：

  丙醇 、 阿魏酸 在 盐酸 作用下， 生成 propyl ferulate
  参考文献：
  名称：

  Antiallergic activity of rosmarinic acid esters is modulated by hydrophobicity, and bulkiness of alkyl side chain

  摘要：

  摘要 对迷迭香酸、咖啡酸和对香豆酸的甲基、丙基和己基酯进行了抗过敏活性测试，其中迷迭香酸丙基酯表现出最大的β-葡萄糖氨酸酶释放抑制作用（IC50，23.7 μM）。在每个酸酯系列中观察到pIC50和cLogP之间的二次相关性（分别为r2 = 0.94、0.98和1.00）。抗过敏活性受疏水性和烷基链的体积影响。

  DOI：

  10.1080/09168451.2015.1010478

文献信息

• Nitrification Inhibitors from the Root Tissues of <i>Brachiaria humidicola</i>, a Tropical Grass
  作者：Subramaniam Gopalakrishnan、Guntur V. Subbarao、Kazuhiko Nakahara、Tadashi Yoshihashi、Osamu Ito、Ikuko Maeda、Hiroshi Ono、Mitsuru Yoshida

  DOI：10.1021/jf062593o

  日期：2007.2.1

  inhibitory compounds were isolated by activity-guided fractionation, using recombinant Nitrosomonas europaea containing luxAB genes derived from the bioluminescent marine gram-negative bacterium Vibrio harveyi. The compounds were identified as methyl-p-coumarate and methyl ferulate, respectively. Their nitrification inhibitory properties were confirmed in chemically synthesized preparations of each.

  在热带牧场草Bracharia Humicola的根组织提取物中发现了硝化抑制活性。使用含有衍生自生物发光海洋革兰氏阴性细菌哈维弧菌的luxAB基因的重组欧洲硝化单胞菌，通过活性指导分离分离了两种活性抑制化合物。这些化合物分别被鉴定为对香豆酸甲酯和阿魏酸甲酯。在各自的化学合成制剂中证实了它们的硝化抑制性能。化学合成制剂的IC50值分别为19.5和4.4 microM。对香豆酸和阿魏酸的乙酯，丙酯和丁酯会抑制硝化作用，而游离酸形式则没有抑制活性。
• Biological activity evaluation and structure–activity relationships analysis of ferulic acid and caffeic acid derivatives for anticancer
  作者：Weixia Li、Nianguang Li、Yuping Tang、Baoquan Li、Li Liu、Xu Zhang、Haian Fu、Jin-ao Duan

  DOI：10.1016/j.bmcl.2012.08.038

  日期：2012.10

  The anticancer activities of alkyl esters and NO-donors of ferulic acid (FA) and caffeic acid (CA) were assessed by a high-throughout screening (HTS) method, and the structure–activity relationships were described. CA alkyl esters had better anticancer activities than FA alkyl esters with the same alkyl substituent. Mono-nitrates and phenylfuroxan nitrates were more potent than the dual nitrates.

  通过高通量筛选（HTS）方法评估了烷基酯和阿魏酸（FA）和咖啡酸（CA）的NO供体的抗癌活性，并描述了结构与活性之间的关系。与具有相同烷基取代基的FA烷基酯相比，CA烷基酯具有更好的抗癌活性。单硝酸盐和苯基呋喃喃硝酸盐比双硝酸盐更有效。FA的苯磺酰呋喃呋喃硝酸盐，尤其是化合物8b - 8d在抗癌方面表现出更强的活性。
• Eco-Friendly Cinnamic Acid Derivatives Containing Glycoside Scaffolds as Potential Antiviral Agents
  作者：Fangping Zhong、Qi Zhang、Kejia Chen、Shichao Lan、Wenchao Yang、Xiuhai Gan

  DOI：10.1021/acs.jafc.3c06318

  日期：2023.11.22

  eco-friendly antiviral agents to control plant viral diseases. In our previous studies, some ferulic acid derivatives with good antiviral activity were obtained as an immune activator. To continue the discovery of eco-friendly antiviral agents, different monosaccharides were introduced into cinnamic acid skeletons by an activity-based strategy to obtain a series of cinnamic acid derivatives containing

  天然产物是开发新型环保抗病毒剂以控制植物病毒病的重要来源。在我们前期的研究中，获得了一些具有良好抗病毒活性的阿魏酸衍生物作为免疫激活剂。为了继续发现环境友好的抗病毒药物，通过基于活性的策略将不同的单糖引入肉桂酸骨架中，获得了一系列含有糖苷支架的肉桂酸衍生物，及其对烟草花叶病毒（TMV）和番茄的抗病毒活性对斑点萎蔫病毒（TSWV）进行了评估。其中，化合物8d对TMV和TSWV的保护活性最强，EC 50值分别为128.5和236.8 μg·mL –1，优于宁南霉素（分别为238.5和315.7 μg·mL –1）。此外，化合物8d可以显着提高过氧化物酶、几丁质酶和β-1,3-葡聚糖酶的防御酶活性。蛋白质组学和转录组分析表明，化合物8d调节基因转录和蛋白质表达水平，参与抵抗病毒感染的防御反应。本研究表明，化合物8d是开发新型、环保、基于天然产物的抗病毒药物的潜在先导候选药物。
• Dependence of Mesomorphism on Molecular Rigidity with Reference to Lateral Substitution and Central Bridge
  作者：J. J. Travadi、M. S. Vadodaria、K. D. Ladva、A. V. Doshi

  DOI：10.1080/15421406.2015.1106273

  日期：2016.2.11

  A novel mesogenic ester homologous series is synthesized and studied with a view to understanding and establishing the effect of laterally substituted -OCH3 on mesomorphic behavior. The series consists of twelve members. C-1 to C-4 members are nonmesogenic, C-6 to C-12 are smectogenic in addition to nematogenic, and C-14 to C-16 are only smectogenic. The textures of smectic and nematic phases are A or C type and threaded or Schlieren, respectively. The transition curves in a phase diagram exhibit an odd-even effect and behave in normal manner except for the C-14 and C-16 derivatives in Sm-I transitions. Thermometric data were determined by an optical polarizing microscope equipped with a heating stage. Average thermal stability for smectic and nematic are 107.7 degrees C and 121.0 degrees C, respectively. Smectogenic and nematogenic mesophase length ranges from 11.0 to 44.0 degrees C and 12.0 degrees C to 39.0 degrees C, respectively. The mesomorphic properties of present series are compared with structurally similar other known series. Thus, present series is predominantly smectogenic and partly nematogenic of middle ordered melting type.