1-[11-(ferulyloxy)undecanoyl]glycerol | 1428651-36-8

• 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: 1-[11-(ferulyloxy)undecanoyl]glycerol
• 英文别名: 2,3-dihydroxypropyl 11-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxyundecanoate
• CAS: 1428651-36-8
• 化学式: C₂₄H₃₆O₈
• 分子量: 452.545
• InChiKey: NANXZYAOTMXOQR-WYMLVPIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  32
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  vinyl ferulate 在 盐酸 、 水 作用下， 以 甲醇 、 正己烷 、 丁酮 为溶剂， 反应 4.0h， 生成 1-[11-(ferulyloxy)undecanoyl]glycerol
  参考文献：
  名称：

  Bioorganic synthesis, characterization and evaluation of a natural phenolic lipid

  摘要：

  The first synthesis of a phenolic natural monoacylglycerol (1- [11-(ferulyloxy) undecanoyl)] glycerol) was carried out by bioorganic synthesis starting from ferulic acid. The synthetic route of the target lipidic compound was designed involving a chemo-enzymatic approach using immobilized Candida antarctica lipase as biocatalyst in two of the steps conducted in organic medium. The prepared lipidic compound was characterized by using spectral data and evaluated for antimicrobial, antioxidant and cytotoxic studies to examine its potential. The synthesized compound showed moderate antimicrobial activity and showed very good antioxidant activity in DPPH radical scavenging assay and also in oxidation inhibition in soybean oil by differential scanning calorimetry. The cytotoxic studies of the synthetic lipid showed promising activity against A549 and HeLa cancer cell lines with IC₅₀ values of 9.102 and 9.886 μM respectively. The prepared compound can be useful in designing novel phenolic lipids with potential applications in cosmetic and biomedical fields.

  DOI：

  10.1016/j.btre.2019.e00375

文献信息

• Bioorganic synthesis, characterization and evaluation of a natural phenolic lipid
  作者：Juliya Johny、Venkateshwarlu Kontham、Dileep Veeragoni、Sunil Misra、Shiva Shanker Kaki

  DOI：10.1016/j.btre.2019.e00375

  日期：2019.12

  The first synthesis of a phenolic natural monoacylglycerol (1- [11-(ferulyloxy) undecanoyl)] glycerol) was carried out by bioorganic synthesis starting from ferulic acid. The synthetic route of the target lipidic compound was designed involving a chemo-enzymatic approach using immobilized Candida antarctica lipase as biocatalyst in two of the steps conducted in organic medium. The prepared lipidic compound was characterized by using spectral data and evaluated for antimicrobial, antioxidant and cytotoxic studies to examine its potential. The synthesized compound showed moderate antimicrobial activity and showed very good antioxidant activity in DPPH radical scavenging assay and also in oxidation inhibition in soybean oil by differential scanning calorimetry. The cytotoxic studies of the synthetic lipid showed promising activity against A549 and HeLa cancer cell lines with IC₅₀ values of 9.102 and 9.886 μM respectively. The prepared compound can be useful in designing novel phenolic lipids with potential applications in cosmetic and biomedical fields.