(Z)-5-hydroxy-1,7-bis(4-O-L-alaninoyl-3-methoxyphenyl)hept-4-en-3-one | 1429402-71-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (Z)-5-hydroxy-1,7-bis(4-O-L-alaninoyl-3-methoxyphenyl)hept-4-en-3-one
• CAS: 1429402-71-0
• 化学式: C₂₇H₃₄N₂O₈
• 分子量: 514.576
• InChiKey: VUYMEHLZJNXCRN-VLPHNSQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.79
• 重原子数：
  37.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  160.4
• 氢给体数：
  3.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  [4-[(1E,6E)-7-[4-[(2S)-2-aminopropanoyl]oxy-3-methoxyphenyl]-3-hydroxy-5-oxohepta-1,3,6-trienyl]-2-methoxyphenyl] (2S)-2-aminopropanoate 在 10 percent palladium on barium sulphate 、 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以95%的产率得到(Z)-5-hydroxy-1,7-bis(4-O-L-alaninoyl-3-methoxyphenyl)hept-4-en-3-one
  参考文献：
  名称：

  Synthesis of amino acid conjugates of tetrahydrocurcumin and evaluation of their antibacterial and anti-mutagenic properties

  摘要：

  Tetrahydrocurcumin (THC), the hydrogenated and stable form of curcumin, exhibits physiological and pharmacological activities similar to curcumin. A protocol has been developed for the synthesis of novel conjugates of THC with alanine (2a), isoleucine (2b), proline (2c), valine (2d), phenylalanine (2e), glycine (21) and leucine (2g) in high yields (43-82%). All the derivatives of THC exhibited more potent anti-microbial activity than THC against Bacillus cereus, Staphylococcus aureus, Escherichia coli and Yersinia enterocolitica. The MIC values of the derivatives were 24-37% of those for THC in case of both Gram-positive and Gram-negative bacteria. Derivatives 2g and 2d exhibited maximum anti-mutagenicity against Salmonella typhimurium TA 98 and TA 1538, respectively at a low concentration of 313 mu g/plate, with comparable activity for THC evident only at 3750 mu g/plate. These results clearly demonstrated that the conjugation of THC at the phenolic position with amino acids led to significant improvement of its in vitro biological attributes. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.foodchem.2013.01.081