4-hydroxy-3-methoxybenzyl erucate | 1261588-25-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-hydroxy-3-methoxybenzyl erucate
• 英文别名: (4-hydroxy-3-methoxyphenyl)methyl (Z)-docos-13-enoate
• CAS: 1261588-25-3
• 化学式: C₃₀H₅₀O₄
• 分子量: 474.725
• InChiKey: VCAYEMIXVGXTTD-KHPPLWFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.9
• 重原子数：
  34
• 可旋转键数：
  23
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  芥酸 、 4-羟基-3-甲氧基苄醇 在 novozyme 435 作用下， 以 叔丁醇 为溶剂， 反应 4.0h， 以61.3%的产率得到4-hydroxy-3-methoxybenzyl erucate
  参考文献：
  名称：

  Evaluation of the Antioxidant Activity of Capsiate Analogues in Polar, Nonpolar, and Micellar Media

  摘要：

  Synthesis of 10 capsiate analogues was conducted by lipase-mediated (Novozyme 435) esterification of vanillyl alcohol with different fatty acids. The antioxidant activity of the synthesized capsiates was evaluated using three in vitro assays: DPPH radical scavenging assay (polar medium), Rancimat assay (nonpolar medium), and autoxidation of linoleic acid (micellar medium). The objective of this study is to find the influence of structural characteristics of the alkyl chain of capsiate analogues on their antioxidant activity. In these assays, BHT and alpha-tocopherol were used as reference compounds. Both DPPH and Rancimat assays did not show any specific trend of antioxidant activity with the increase in lipophilicity and also with the type of fatty acids grafted to the phenolic moiety. In the Tween 20 micellar system for the inhibition of autoxidation of linoleic acid, vanillyl ester attached to a C18 alkyl chain (vanillyl stearate, oleate and ricinoleate) exhibited maximum inhibition of autoxidation of linoleic acid.

  DOI：

  10.1021/jf104244m

文献信息

• Evaluation of the Antioxidant Activity of Capsiate Analogues in Polar, Nonpolar, and Micellar Media
  作者：Kunduru K. Reddy、Thumu Ravinder、Rachapudi B. N. Prasad、Sanjit Kanjilal

  DOI：10.1021/jf104244m

  日期：2011.1.26

  Synthesis of 10 capsiate analogues was conducted by lipase-mediated (Novozyme 435) esterification of vanillyl alcohol with different fatty acids. The antioxidant activity of the synthesized capsiates was evaluated using three in vitro assays: DPPH radical scavenging assay (polar medium), Rancimat assay (nonpolar medium), and autoxidation of linoleic acid (micellar medium). The objective of this study is to find the influence of structural characteristics of the alkyl chain of capsiate analogues on their antioxidant activity. In these assays, BHT and alpha-tocopherol were used as reference compounds. Both DPPH and Rancimat assays did not show any specific trend of antioxidant activity with the increase in lipophilicity and also with the type of fatty acids grafted to the phenolic moiety. In the Tween 20 micellar system for the inhibition of autoxidation of linoleic acid, vanillyl ester attached to a C18 alkyl chain (vanillyl stearate, oleate and ricinoleate) exhibited maximum inhibition of autoxidation of linoleic acid.