octyl ferulate | 214779-01-8

• 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 ferulate
• 英文别名: octacyl ferulate；octyl 3-(4-hydroxy-3-methoxyphenyl)-2-propenoate；Octyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• CAS: 214779-01-8
• 化学式: C₁₈H₂₆O₄
• 分子量: 306.402
• InChiKey: PBTJWDSMUBVOKC-UHFFFAOYSA-N

物化性质

• 沸点：
  430.8±30.0 °C(Predicted)
• 密度：
  1.062±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  22
• 可旋转键数：
  11
• 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：

  octyl ferulate 在 lithium dimethylamide 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  블루라이트 차단용 유기 합성물

  摘要：

  본 발명은 블루라이트 차단용 유기 합성물에 관한 것이다. 본 발명에 따른 블루라이트 차단용 유기 합성물은 하기의 [화학식 1]로 표현되는 페룰릴 산 유도체를 포함한다. [화학식 1] 여기서, R1, R2, R3 = H, CnH2n+1 또는 CnH2n-1 (n은 1~16) M = Li, Na 또는 K 상기한 구성에 의해 본 발명에 따른 블루라이트 차단용 유기 합성물은 페룰린 산(Ferulic Acid)이 출발물질로 사용되어 합성됨으로써, 인체에 유해한 블루라이트를 효과적으로 차폐하고 블루라이트에 의해 시력이 저하되는 것을 방지하며 눈의 피로감이나 두통 등을 유발할 수 있는 인자를 제거할 수 있다.

  公开号：

  KR102389476B1
• 作为产物：
  描述：

  辛醇 、 阿魏酸甲酯 在 Novozym₄₃₅ 、 Amberlite IR-120H 作用下， 以 甲醇 为溶剂， 生成 octyl ferulate
  参考文献：
  名称：

  Evaluation of deep eutectic solvent–water binary mixtures for lipase-catalyzed lipophilization of phenolic acids

  摘要：

  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。

  DOI：

  10.1039/c3gc40899j

文献信息

• Ionic Liquid-Assisted Solubilization for Improved Enzymatic Esterification of Phenolic Acids
  作者：Zhiyong Yang、Zheng Guo、Xuebing Xu

  DOI：10.1007/s11746-011-1989-3

  日期：2012.6

  derivatives. This work reports a novel approach to improve Candida antartica lipase B (Novozym 435) catalyzed lipophilization of phenolic acids by means of ionic liquids (IL), trioctylmethylammonium trifluoroacetate (tOMA.TFA) assisted solubilization of the substrate. In this approach, the IL plays two major roles, namely, to dissolve phenolic acids at high concentration so as to create a homogeneous system

  酚酸的亲脂性衍生物可以极大地扩展其在亲脂性生物环境和食品加工中的应用，因此，开发有效的亲脂性反应体系构成了生物催化的一个有趣课题。酚酸在大多数酶良性溶剂中的低溶解度是造成亲脂性酚类衍生物酶促生产效率低下的主要原因。这项工作报告了一种新颖的方法，可通过离子液体（IL），三辛基甲基三氟乙酸铵（t）来改善南极假丝酵母脂肪酶B（Novozym 435）催化的酚酸脂化。OMA.TFA）有助于底物的溶解。在这种方法中，IL发挥了两个主要作用，即以高浓度溶解酚酸，从而与另一种底物1-辛醇形成均相系统，并对酶保持良性，从而保持生物催化剂的活性。事实证明，这本身就是一种正确的策略，因为可以提高转化率和提高生产率。结果表明，IL的用量（以1-辛醇/ t OMA.TFA的体积比表示），二氢咖啡酸（DHCA）的浓度和温度是控制反应效率的关键参数。DHCA的最大转化率是1-辛醇/吨OMA.TFA 12：1（v / v）（1-辛醇/
• 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.
• Alkyl Ferulate Esters as Multifunctional Food Additives: Antibacterial Activity and Mode of Action against <i>Escherichia coli</i> in Vitro
  作者：Yu-gang Shi、Yun-jie Zhu、Shi-yin Shao、Run-run Zhang、Yu Wu、Chen-min Zhu、Xian-rui Liang、Wen-qiang Cai

  DOI：10.1021/acs.jafc.8b04429

  日期：2018.11.14

  This work aims to prepare ferulic acid alkyl esters (FAEs) through the lipase-catalyzed reaction between methyl ferulate and various fatty alcohols in deep eutectic solvents and ascertain their antibacterial activities and mechanisms. Screens of antibacterial effects of FAEs against Escherichia coli ATCC 25922 (E. coli) and Listeria monocytogenes ATCC 19115 (L. monocytogenes) revealed that hexyl ferulate (FAC6) exerted excellent bacteriostatic and bactericidal effects on E. coli and L. monocytogenes (minimum inhibitory concentration (MIC): 1.6 and 0.1 mM, minimum bactericidal concentration (MBC): 25.6 and 0.2 mM, respectively). The antibacterial mechanism of FAC6 against E. coli was systematically studied to facilitate its practical use as a food additive with multifunctionalities. The growth and time-kill curves implied the partial cell lysis and inhibition of the growth of E. coli caused by FAC6. The result related to propidium iodide uptake and cell constituents' leakage (K+, proteins, nucleotides, and beta-galactosidase) implied that bacterial cytomembranes were substantially compromised by FAC6. Variations on morphology and cardiolipin microdomains and membrane hyperpolarization of cells visually verified that FAC6 induced cell elongation and destructed the cell membrane with cell wall perforation. SDS-PAGE analysis and alterations of fluorescence spectra of bacterial membrane proteins manifested that FAC6 caused significant changes in constitutions and conformation of membrane proteins. Furthermore, it also could bind to minor grooves of E. coli DNA to form complexes. Meanwhile, FAC6 exhibited antibiofilm formation activity. These findings indicated that that FAC6 has promising potential to be developed as a multifunctional food additive.