(E)-N-(caffeic acid)-L-glycinate ethyl ester | 1332371-16-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (E)-N-(caffeic acid)-L-glycinate ethyl ester
• 英文别名: ethyl (E)-2-(3-(3,4-dihydroxyphenyl)acrylamido)acetate；ethyl 2-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]amino]acetate
• CAS: 1332371-16-0
• 化学式: C₁₃H₁₅NO₅
• 分子量: 265.266
• InChiKey: QMSNIUNROXDEHM-GQCTYLIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  95.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-N-(caffeic acid)-L-glycinate ethyl ester 、 溴代十二烷 在 potassium carbonate 、 potassium iodide 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以92%的产率得到ethyl (E)-2-(3-(4-dodecyloxy-3-hydroxyphenyl)acrylamido)acetate
  参考文献：
  名称：

  New Multifunctional Surfactants from Natural Phenolic Acids

  摘要：

  Several new multifunctional molecules derived from natural sources such as amino acids and hydroxycinnamic acids were synthesized. They exhibit various activities such as emulsifying, UV-protecting, and radical scavenging, thereby conforming to the latest requirements for cosmetic ingredients. The synthesis comprises only a few steps: (i) the amino acid, the acid groups of which are protected by esterification, is coupled with ferulic or caffeic acid; (ii) the p-hydroxyl group of the cinnamic derivative reacts with dodecyl bromide in the presence of potassium carbonate (the resulting compounds are highly lipophilic and tested as water/oil (W/O) emulsifiers); (iii) these molecules, by deprotonating the acid groups of the amino acids, with successive salification, are more hydrophilic, with stronger O/W emulsifying properties. The new multifunctional surfactants might prove useful for the treatment of multiple skin conditions, including loss of cellular antioxidants, damage from free radicals, damage from UV, and others.

  DOI：

  10.1021/jf203133w
• 作为产物：
  描述：

  咖啡酸 、 甘氨酸乙酯盐酸盐 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N-甲基吗啉 作用下， 以 N,N-二甲基甲酰胺 、 二氯甲烷 为溶剂， 反应 21.17h， 以60%的产率得到(E)-N-(caffeic acid)-L-glycinate ethyl ester
  参考文献：
  名称：

  N-羟基肉桂酰基酰胺衍生物的合成及其抗氧化和抗酪氨酸酶活性的评估。

  摘要：

  以1-氨基酸乙酯盐酸盐和相应的肉桂酸（阿魏酸，乙酰基阿魏酸和咖啡酸）为原料，在催化量为1-的条件下，合成了十二种N-羟基肉桂酰基氨基酸酰胺乙酯（CAES）。 （3-二甲基氨基丙基）-3-乙基碳二亚胺盐酸盐（EDC）和1-羟基苯并三烯（HOBt）。评价了CAES的1，1-二苯基-2-吡啶并肼基（DPPH）清除自由基的活性。的抗酪氨酸酶活Ñ -feruloyl氨基酸乙酯和羟基（OH ）的自由基清除活性N-还检验咖啡酰氨基酸乙酯。在所有CAES中均显示了DPPH清除自由基的活性，其中N-咖啡酰氨基酸乙酯比N-阿魏酰酰胺衍生物具有更高的自由基清除活性，并且（E）-N-（咖啡酸）-1-甘氨酸乙酯（c 5）具有最强的清除自由基的能力。 IC 50值为18.6 µM。在测试的酰胺中，乙酰基阿魏酸氨基酸酯显示出最高的酪氨酸酶抑制活性。

  DOI：

  10.1016/j.bmc.2019.05.031

文献信息

• Synthesis of N-hydroxycinnamoyl amide derivatives and evaluation of their anti-oxidative and anti-tyrosinase activities
  作者：Dong Wang、Jun Zhu、Jin-Rong Xu、Dan-Dan Ji

  DOI：10.1016/j.bmc.2019.05.031

  日期：2019.10

  scavenging activities of CAES were evaluated. The anti-tyrosinase activities of N-feruloyl amino acid ethyl esters and the hydroxyl (OH) free radical scavenging activities of N-caffeoyl amino acid ethyl esters were also examined. DPPH free radical scavenging activity was shown in all CAES, of which N-caffeoyl amino acid ethyl esters demonstrated higher radical scavenging activity than N-feruloyl amide derivatives

  以1-氨基酸乙酯盐酸盐和相应的肉桂酸（阿魏酸，乙酰基阿魏酸和咖啡酸）为原料，在催化量为1-的条件下，合成了十二种N-羟基肉桂酰基氨基酸酰胺乙酯（CAES）。 （3-二甲基氨基丙基）-3-乙基碳二亚胺盐酸盐（EDC）和1-羟基苯并三烯（HOBt）。评价了CAES的1，1-二苯基-2-吡啶并肼基（DPPH）清除自由基的活性。的抗酪氨酸酶活Ñ -feruloyl氨基酸乙酯和羟基（OH ）的自由基清除活性N-还检验咖啡酰氨基酸乙酯。在所有CAES中均显示了DPPH清除自由基的活性，其中N-咖啡酰氨基酸乙酯比N-阿魏酰酰胺衍生物具有更高的自由基清除活性，并且（E）-N-（咖啡酸）-1-甘氨酸乙酯（c 5）具有最强的清除自由基的能力。 IC 50值为18.6 µM。在测试的酰胺中，乙酰基阿魏酸氨基酸酯显示出最高的酪氨酸酶抑制活性。
• New Multifunctional Surfactants from Natural Phenolic Acids
  作者：Marisanna Centini、Maria Sole Rossato、Alessandro Sega、Anna Buonocore、Sara Stefanoni、Cecilia Anselmi

  DOI：10.1021/jf203133w

  日期：2012.1.11

  Several new multifunctional molecules derived from natural sources such as amino acids and hydroxycinnamic acids were synthesized. They exhibit various activities such as emulsifying, UV-protecting, and radical scavenging, thereby conforming to the latest requirements for cosmetic ingredients. The synthesis comprises only a few steps: (i) the amino acid, the acid groups of which are protected by esterification, is coupled with ferulic or caffeic acid; (ii) the p-hydroxyl group of the cinnamic derivative reacts with dodecyl bromide in the presence of potassium carbonate (the resulting compounds are highly lipophilic and tested as water/oil (W/O) emulsifiers); (iii) these molecules, by deprotonating the acid groups of the amino acids, with successive salification, are more hydrophilic, with stronger O/W emulsifying properties. The new multifunctional surfactants might prove useful for the treatment of multiple skin conditions, including loss of cellular antioxidants, damage from free radicals, damage from UV, and others.