methyl 12-[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyloxy]octadecanoate | 1383325-24-3

• 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: methyl 12-[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyloxy]octadecanoate
• CAS: 1383325-24-3
• 化学式: C₂₉H₄₆O₆
• 分子量: 490.681
• InChiKey: MKSVSOXBXHYJFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.37
• 重原子数：
  35.0
• 可旋转键数：
  20.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  82.06
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  阿魏酸 、 12-羟基硬脂酸甲酯 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以49.2%的产率得到methyl 12-[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyloxy]octadecanoate
  参考文献：
  名称：

  Synthesis and evaluation of antioxidant and antifungal activities of novel ricinoleate-based lipoconjugates of phenolic acids

  摘要：

  Syntheses of four castor oil fatty acid-based novel lipoconjugates of phenolic acids were carried out following Mitsunobu methodology. The lipid part consists of methyl ricinoleate and its saturated analogue, methyl-12-hydroxystearate and the phenolic moieties are ferulic and vanillic acid. Synthesised compounds are evaluated for antioxidant activity using three in vitro assays (DPPH radical scavenging assay, DSC studies for oxidative induction temperature of linoleic acid and autoxidation of linoleic acid in Tween 20 micellar medium) and compared with three widely used antioxidants in the food industry, BHT, alpha-tocopherol, and dodecyl gallate. Synthesised compounds are found to exhibit good antiradical activity. These compounds also exhibited very good antifungal activity against studied fungal strains. All these results suggested the applicability of the synthesised compounds as potent lipophilic antioxidants for combating oxidative stress. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.foodchem.2012.04.046