lauryl ferulate | 87024-34-8

• 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: lauryl ferulate
• 英文别名: dodecyl ferulate；Dodecyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• CAS: 87024-34-8
• 化学式: C₂₂H₃₄O₄
• 分子量: 362.51
• InChiKey: GSGVKEOQRLQPPH-UHFFFAOYSA-N

物化性质

• 熔点：
  44-45 °C
• 沸点：
  481.3±30.0 °C(Predicted)
• 密度：
  1.022±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  26
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 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：

  lauryl ferulate 、 二氯甲烷 在 18-冠醚-6 potassium carbonate 作用下， 反应 24.0h， 以85.69%的产率得到bis-4,4'-(2-dodecyloxycarbonyl-1-ethenyl)-2,2'-methoxyphenoxymethane
  参考文献：
  名称：

  Thermally stable ferulic acid derivatives

  摘要：

  一种由通式（1）表示的香豆酸衍生物；一种制备由通式（1）表示的香豆酸衍生物的方法，包括将由通式（2）表示的香豆酸或其酯与由通式CH2X2表示的二卤甲烷（其中X是卤素原子）反应；以及包含该香豆酸衍生物的紫外光吸收组合物。由于该紫外光吸收组合物不仅在紫外光吸收方面表现出色，而且对热稳定性非常好，因此该紫外光吸收组合物可作为特别需要长期稳定性的化妆品而合适地使用。

  公开号：

  US20040152912A1
• 作为产物：
  描述：

  癸醇 、 feruloyl CoA 在 recombinant Marchantia emarginata hydroxycinnamoyl transferase 作用下， 以 aq. buffer 为溶剂， 反应 0.17h， 生成 lauryl ferulate
  参考文献：
  名称：

  Functional Characterization of a Hydroxyacid/Alcohol Hydroxycinnamoyl Transferase Produced by the Liverwort Marchantia emarginata

  摘要：

  陆生植物的地上器官覆盖着一层疏水的保护性角质层。角质层的主要成分是脂质聚酯——角质，它由脂肪族和芳香族结构域组成。脂肪族部分是一种脂肪酸/醇和羟基肉桂酰酸之间的聚酯。BAHD/HxxxD家族酶是这些聚酯合成过程的核心。迄今为止，这类酶在苔藓植物中的性质尚未被探究。本文从地钱（Marchantium emarginatum）中分离出一个编码脂肪酸ω-羟酸/脂肪酸醇羟基肉桂酰转移酶（HFT）的基因，并进行了功能表征。基于重组蛋白的实验表明，该酶以ω-羟基脂肪酸或初级醇作为其酰基受体，以各种羟基肉桂酰-CoA——优选阿魏酰-CoA和咖啡酰-CoA——作为酰基供体，至少在体外如此。在地钱叶片中短暂表达MeHFT-GFP融合转基因表明，MeHFT被导向细胞质，这表明角质单体的阿魏化作用发生在那里。

  DOI：

  10.3390/molecules22111854

文献信息

• Solvent-free Lipase-Catalyzed Preparation of Long-Chain Alkyl Phenylpropanoates and Phenylpropyl Alkanoates
  作者：Klaus Vosmann、Petra Weitkamp、Nikolaus Weber

  DOI：10.1021/jf060052t

  日期：2006.4.1

  An enzymatic method was developed for the preparation of medium- or long-chain alkyl 3-phenylpropenoates (alkyl cinnamates), particularly alkyl hydroxy- and methoxy-substituted cinnamates such as oleyl p-coumarate and oleyl ferulate. The various alkyl cinnamates were formed in high to moderate yield by lipase-catalyzed esterification of cinnamic acid and its analogues with fatty alcohols in vacuo at moderate temperatures in the absence of drying agents and solvents. Immobilized Candida antarctica lipase B was the most effective biocatalyst for the various esterification reactions. The relative esterification activities were of the following order: clihydrocinnamic > cinnamic > 3-methoxycinnamic > dihydrocaffeic approximate to 3-hydroxycinnamic > 4-methoxycinnamic > 2-methoxycinnamic > 4-hydroxycinnamic > ferulic approximate to 3,4-dimethoxycinnamic > 2-hydroxycinnamic acid. With respect to the position of the substituents at the phenyl moiety, the esterification activity increased in the order meta > para > ortho. Rhizomucor miehei lipase demonstrated moderate esterification activity. Compounds with inverse chemical structure, that is, 3-phenylpropyl alkanoates such as 3-(4-hydroxyphenyl)propyl oleate, were also obtained in high yield by esterification of fatty acids with the corresponding 3-phenylpropan-1-ols.
• 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.
• Thermally stable ferulic acid derivatives
  申请人：——

  公开号：US20040152912A1

  公开（公告）日：2004-08-05

  A ferulic acid derivative represented by the general formula (1); a process for preparing a ferulic acid derivative represented by the general formula (1), comprising reacting ferulic acid or an ester thereof represented by the general formula (2) with a dihalomethane represented by the general formula CH 2 X 2 , wherein X is a halogen atom; and an ultraviolet light-absorbent composition comprising the ferulic acid derivative. Since the ultraviolet light absorbent composition is not only excellent in the ultraviolet light absorption but also very stable against heat, the ultraviolet light absorbent composition can be suitably used as cosmetics which especially require long-term stability.

  一种由通式（1）表示的香豆酸衍生物；一种制备由通式（1）表示的香豆酸衍生物的方法，包括将由通式（2）表示的香豆酸或其酯与由通式CH2X2表示的二卤甲烷（其中X是卤素原子）反应；以及包含该香豆酸衍生物的紫外光吸收组合物。由于该紫外光吸收组合物不仅在紫外光吸收方面表现出色，而且对热稳定性非常好，因此该紫外光吸收组合物可作为特别需要长期稳定性的化妆品而合适地使用。
• Functional Characterization of a Hydroxyacid/Alcohol Hydroxycinnamoyl Transferase Produced by the Liverwort Marchantia emarginata
  作者：Ping-Ping Wang、Hui Liu、Shuai Gao、Ai-Xia Cheng

  DOI：10.3390/molecules22111854

  日期：——

  The aerial organs of most terrestrial plants are covered by a hydrophobic protective cuticle. The main constituent of the cuticle is the lipid polyester cutin, which is composed of aliphatic and aromatic domains. The aliphatic component is a polyester between fatty acid/alcohol and hydroxycinnamoyl acid. The BAHD/HxxxD family enzymes are central to the synthesis of these polyesters. The nature of this class of enzymes in bryophytes has not been explored to date. Here, a gene encoding a fatty ω-hydroxyacid/fatty alcohol hydroxycinnamoyl transferase (HFT) has been isolated from the liverwort Marchantia emarginata and has been functionally characterized. Experiments based on recombinant protein showed that the enzyme uses ω-hydroxy fatty acids or primary alcohols as its acyl acceptor and various hydroxycinnamoyl-CoAs—preferentially feruloyl-CoA and caffeoyl-CoA—as acyl donors at least in vitro. The transient expression of a MeHFT-GFP fusion transgene in the Nicotiana benthamiana leaf demonstrated that MeHFT is directed to the cytoplasm, suggesting that the feruloylation of cutin monomers takes place there.

  陆生植物的地上器官覆盖着一层疏水的保护性角质层。角质层的主要成分是脂质聚酯——角质，它由脂肪族和芳香族结构域组成。脂肪族部分是一种脂肪酸/醇和羟基肉桂酰酸之间的聚酯。BAHD/HxxxD家族酶是这些聚酯合成过程的核心。迄今为止，这类酶在苔藓植物中的性质尚未被探究。本文从地钱（Marchantium emarginatum）中分离出一个编码脂肪酸ω-羟酸/脂肪酸醇羟基肉桂酰转移酶（HFT）的基因，并进行了功能表征。基于重组蛋白的实验表明，该酶以ω-羟基脂肪酸或初级醇作为其酰基受体，以各种羟基肉桂酰-CoA——优选阿魏酰-CoA和咖啡酰-CoA——作为酰基供体，至少在体外如此。在地钱叶片中短暂表达MeHFT-GFP融合转基因表明，MeHFT被导向细胞质，这表明角质单体的阿魏化作用发生在那里。