octyl p-coumarate | 193343-08-7

• 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: octyl p-coumarate
• 英文别名: octacyl coumarate；octyl coumarate；octyl 3-(4-hydroxyphenyl)prop-2-enoate
• CAS: 193343-08-7
• 化学式: C₁₇H₂₄O₃
• 分子量: 276.376
• InChiKey: JSLXRMDKYVPFAJ-UHFFFAOYSA-N

物化性质

• 沸点：
  403.4±20.0 °C(Predicted)
• 密度：
  1.045±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  octyl p-coumarate 在 potassium osmate(VI) 、 N-甲基吗啉氧化物 、 sodium hydroxide 作用下， 以 水 、 丙酮 、 乙腈 为溶剂， 反应 18.0h， 生成
  参考文献：
  名称：

  Chemo-Enzymatic Synthesis and Biological Assessment of p-Coumarate Fatty Esters: New Antifungal Agents for Potential Plant Protection

  摘要：

  农业的一个趋势是用更环保的解决方案取代传统的杀虫剂，例如激发法，这是一种很有前途的方法，它通过刺激植物的天然免疫系统来提高植物对病原体的抵抗力。为此，我们根据尽可能多的绿色化学原则合成了一个对香豆素类化合物库。然后，对这些分子进行了以下测试：(1) 直接抑制两种病原体--灰霉病菌和硬皮病菌--的菌丝生长；(2) 拟南芥和油菜质膜失稳。最后，对拟南芥/B. cinerea病原系统的保护作用进行了评估。使用二羟基化脂肪对香豆酸酯可以完全抑制两种真菌的生长，并观察到明显的离子泄漏。对植物的直接影响还体现在坏死面积减少了约三倍。

  DOI：

  10.3390/molecules28155803
• 作为产物：
  描述：

  对羟基肉桂酸 在 盐酸 、 Novozym 435 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 生成 octyl p-coumarate
  参考文献：
  名称：

  Chemo-Enzymatic Synthesis and Biological Assessment of p-Coumarate Fatty Esters: New Antifungal Agents for Potential Plant Protection

  摘要：

  农业的一个趋势是用更环保的解决方案取代传统的杀虫剂，例如激发法，这是一种很有前途的方法，它通过刺激植物的天然免疫系统来提高植物对病原体的抵抗力。为此，我们根据尽可能多的绿色化学原则合成了一个对香豆素类化合物库。然后，对这些分子进行了以下测试：(1) 直接抑制两种病原体--灰霉病菌和硬皮病菌--的菌丝生长；(2) 拟南芥和油菜质膜失稳。最后，对拟南芥/B. cinerea病原系统的保护作用进行了评估。使用二羟基化脂肪对香豆酸酯可以完全抑制两种真菌的生长，并观察到明显的离子泄漏。对植物的直接影响还体现在坏死面积减少了约三倍。

  DOI：

  10.3390/molecules28155803

文献信息

• Evaluation of deep eutectic solvent–water binary mixtures for lipase-catalyzed lipophilization of phenolic acids
  作者：Erwann Durand、Jérôme Lecomte、Bruno Baréa、Eric Dubreucq、Robert Lortie、Pierre Villeneuve

  DOI：10.1039/c3gc40899j

  日期：——

  This work reports the first lipase-catalyzed reactions between substrates of different polarities using deep eutectic solvents as a medium. The model reaction consisted of a lipophilization process based on the alcoholysis of phenolic esters using immobilized Candida antarctica lipase B as a biocatalyst. Results showed that water could dramatically improve the lipase activity and change the reactivity of phenolic substrates. Indeed, very low conversions (<2%) were observed in pure DES, whereas in DES–water binary mixtures, quantitative conversions were achieved. After investigating the role of various parameters, such as the substrate concentration and ratio, pH or thermodynamic activity of water, the effect of the presence of water in pure DES based on urea or glycerol was discussed. In this paper, we propose new perspectives for the enzymatic modification of polar substrates using this novel generation of green, inexpensive and easy-to-handle solvents.

  这项研究首次报道了以深共晶溶剂为介质催化不同极性底物之间的脂肪酶反应。模型反应包括一个基于酚酯醇解的亲脂化过程，使用固定化的南极念珠菌脂肪酶 B 作为生物催化剂。结果表明，水能显著提高脂肪酶的活性，并改变酚类底物的反应活性。事实上，在纯 DES 中观察到的转化率非常低（小于 2%），而在 DESâ 水的二元混合物中则实现了定量转化。在研究了底物浓度和比例、pH 值或水的热力学活性等各种参数的作用后，我们讨论了在基于尿素或甘油的纯 DES 中水的存在所产生的影响。在本文中，我们提出了使用这种新一代绿色、廉价和易于处理的溶剂对极性底物进行酶修饰的新前景。
• 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.
• Chemo-Enzymatic Synthesis and Biological Assessment of p-Coumarate Fatty Esters: New Antifungal Agents for Potential Plant Protection
  作者：Cyrian Thaeder、Juliette Stanek、Julien Couvreur、Célia Borrego、Fanny Brunissen、Florent Allais、Amandine L. Flourat、Sylvain Cordelier

  DOI：10.3390/molecules28155803

  日期：——

  One trend in agriculture is the replacement of classical pesticides with more ecofriendly solutions, such as elicitation, which is a promising approach consisting of stimulating the natural immune system of a plant to improve its resistance to pathogens. In this fashion, a library of p-coumaric-based compounds were synthesized in accordance with as many principles of green chemistry as possible. Then, these molecules were tested for (1) the direct inhibition of mycelium growth of two pathogens, Botrytis cinerea and Sclerotinia sclerotiorum, and (2) plasma membrane destabilization in Arabidopsis and rapeseed. Finally, the protective effect was evaluated on an Arabidopsis/B. cinerea pathosystem. Total inhibition of the growth of both fungi could be achieved, and significant ion leakage was observed using dihydroxylated fatty p-coumarate esters. A direct effect on plants was also recorded as a ca. three-fold reduction in the necrosis area.

  农业的一个趋势是用更环保的解决方案取代传统的杀虫剂，例如激发法，这是一种很有前途的方法，它通过刺激植物的天然免疫系统来提高植物对病原体的抵抗力。为此，我们根据尽可能多的绿色化学原则合成了一个对香豆素类化合物库。然后，对这些分子进行了以下测试：(1) 直接抑制两种病原体--灰霉病菌和硬皮病菌--的菌丝生长；(2) 拟南芥和油菜质膜失稳。最后，对拟南芥/B. cinerea病原系统的保护作用进行了评估。使用二羟基化脂肪对香豆酸酯可以完全抑制两种真菌的生长，并观察到明显的离子泄漏。对植物的直接影响还体现在坏死面积减少了约三倍。