1(3)-feruloyl dibutyryl glyceride | 1075207-65-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 1(3)-feruloyl dibutyryl glyceride
• 英文别名: 1(3)-feruloyl dibutyryl-glycerol；[2-butanoyloxy-3-[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyloxy]propyl] butanoate
• CAS: 1075207-65-6
• 化学式: C₂₁H₂₈O₈
• 分子量: 408.449
• InChiKey: BCIZIZFFRUQRNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  29.0
• 可旋转键数：
  12.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  108.36
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  甘油三丁酸酯 、 阿魏酸乙酯 在 Novozyme 435 作用下， 以 甲苯 为溶剂， 生成 1(3)-feruloyl monobutyryl-glycerol 、 1(3)-feruloyl dibutyryl glyceride
  参考文献：
  名称：

  Enhancement in the Synthesis of Novel Feruloyl Lipids (Feruloyl Butyryl Glycerides) by Enzymatic Biotransformation Using Response Surface Methodology

  摘要：

  Response surface methodology was successfully employed to optimize lipase-catalyzed synthesis of feruloyl butyryl glycerides (FBGs). The effects of the reaction parameters, including the reaction time, reaction temperature, enzyme concentration, substrate molar ratio, and water activity, and the interaction parameters were examined. The analysis suggested that the conversion of the FBGs was significantly (p < 0.05) affected by independent factors of reaction time, reaction temperature, substrate molar ratio, and water activity as well as interactive terms of reaction temperature/reaction time, reaction temperature/enzyme concentration, substrate molar ratio/reaction temperature, water activity/reaction temperature, reaction time/enzyme concentration, and enzyme concentration/water activity. The highest conversion yield of FBGs was 81.2% at the following optimized reaction conditions: reaction temperature of 53.6 degrees C, reaction time of 5.5 days, enzyme concentration of 50.8 mg/mL, water activity of 0.14, and substrate molar ratio of 2.9. The conversion is higher as compared to that at the conditions before optimization.

  DOI：

  10.1021/jf802478r

文献信息

• Enzymatic Synthesis of Novel Feruloylated Lipids and Their Evaluation as Antioxidants
  作者：Yan Zheng、Christopher Branford‐White、Xiao‐Mei Wu、Cheng‐Yao Wu、Jian‐Gang Xie、Jing Quan、Li‐Min Zhu

  DOI：10.1007/s11746-009-1496-y

  日期：2010.3

  AbstractConcerns about the use of chemical synthetic antioxidants that promote carcinogenesis has led to the development of natural antioxidants. Ferulic acid (4‐hydroxy‐3‐methoxy cinnamic acid, FA) is a monophenolic phenylpropanoid present in the plant kingdom. It has shown a high antioxidant capacity and biological activities, including antiviral, anticarcinogenic and antimicrobial ones. However, due to poor solubility in hydrophobic media, FA can only be used in aqueous environments and this is a key factor that to a certain extent limits its application and bioavailability. In the present study, novel feruloylated lipids 1(3)‐feruloyl‐monobutyryl‐glycerol (FMB) and 1(3)‐feruloyl‐dibutyryl‐glycerol (FDB) were prepared by lipase‐catalysed transesterification between FA and tributyrin. The structure of FMB and FDB was confirmed by NMR and ESI‐MS, respectively. The radical scavenging and antioxidant properties of FA, FMB and FDB were evaluated using several different antioxidant assays, including hydroxyl radical scavenging, superoxide anion radical scavenging, 1,1‐diphenyl‐2‐picrylhydrazyl (DPPH·) radical scavenging, inhibition of peroxidation of linoleic acid and reducing power. The antioxidant activities decreased in the following order: BHT ≥ FMB > FDB > FA. The results suggested that FMB and FDB exhibited a strong effect against oxidation in lipophilic systems making them promising antioxidants.