1-(2,3,4-trimethoxy-6-methoxymethoxyphenyl)-ethanone | 944828-44-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2,3,4-trimethoxy-6-methoxymethoxyphenyl)-ethanone
• CAS: 944828-44-8
• 化学式: C₁₃H₁₈O₆
• 分子量: 270.282
• InChiKey: RHTWGQHKIIAGAM-UHFFFAOYSA-N

物化性质

• 沸点：
  394.6±42.0 °C(Predicted)
• 密度：
  1.126±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-(2,3,4-trimethoxy-6-methoxymethoxyphenyl)-ethanone 、 3,5-dimethoxy-4-(methoxymethoxy)benzaldehyde 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 10.0h， 以75%的产率得到1-(2,3,4-trimethoxy-6-methoxymethoxyphenyl)-3-(3,5-dimethoxy-4-methoxymethoxyphenyl)-2-propen-1-one
  参考文献：
  名称：

  Preparation of two sets of 5,6,7-trioxygenated dihydroflavonol derivatives as free radical scavengers and neuronal cell protectors to oxidative damage

  摘要：

  An unusual class of 5,6,7-trioxygenated dihydroflavonols (3a-e and 4a-j) were designed and prepared. Their antioxidative properties were assessed by examining their capacities in several in vitro models, including superoxide anion and 1,1-diphenyl-2-picrylhydrazyl ( DPPH) radical scavenging, rat liver homogenate lipid peroxidation inhibition, PC12 cells protection from oxidative damage, and xanthine oxidase inhibition. These dihydroflavonols displayed positive quenching abilities towards O-2(center dot-) and DPPH free radicals, in which the majority exhibited superior antioxidant properties to Vitamin C. cis-Configurated compound (+/-)-3e demonstrated remarkable inhibition to LPO with an IC50 value of 1.9 +/- 0.3 mu M, which was apparently stronger than that of quercetin (IC50 = 6.0 +/- 0.4 mu M). trans-Configurated dihydroflavonol (+/-)-4h exhibited significant protective effect on PC12 cells against oxidative damage with an EC50 value of 41.5 +/- 5.3 mu M, more effective compared to that of quercetin (EC50 = 81.8 +/- 8.7 mu M). The 6-OH-5,7-dimethoxy analogue (+/-)-3d showed significant inhibition of xanthine oxidase with an IC50 value of 16.0 +/- 0.8 mu M, which is superior to that of allopurinol (IC50 = 23.5 +/- 2.0 mu M). In addition to the hypothesized action mechanism of the bio-active compounds, 3D modeling was used to analyze the relationship between the minimized-energy structures and antioxidant activities. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.03.032
• 作为产物：
  描述：

  2,3,4-三甲氧基-6-羟基苯乙酮 、 氯甲基甲基醚 在 sodium hydroxide 、 四丁基溴化铵 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 8.25h， 以85%的产率得到1-(2,3,4-trimethoxy-6-methoxymethoxyphenyl)-ethanone
  参考文献：
  名称：

  Preparation of two sets of 5,6,7-trioxygenated dihydroflavonol derivatives as free radical scavengers and neuronal cell protectors to oxidative damage

  摘要：

  An unusual class of 5,6,7-trioxygenated dihydroflavonols (3a-e and 4a-j) were designed and prepared. Their antioxidative properties were assessed by examining their capacities in several in vitro models, including superoxide anion and 1,1-diphenyl-2-picrylhydrazyl ( DPPH) radical scavenging, rat liver homogenate lipid peroxidation inhibition, PC12 cells protection from oxidative damage, and xanthine oxidase inhibition. These dihydroflavonols displayed positive quenching abilities towards O-2(center dot-) and DPPH free radicals, in which the majority exhibited superior antioxidant properties to Vitamin C. cis-Configurated compound (+/-)-3e demonstrated remarkable inhibition to LPO with an IC50 value of 1.9 +/- 0.3 mu M, which was apparently stronger than that of quercetin (IC50 = 6.0 +/- 0.4 mu M). trans-Configurated dihydroflavonol (+/-)-4h exhibited significant protective effect on PC12 cells against oxidative damage with an EC50 value of 41.5 +/- 5.3 mu M, more effective compared to that of quercetin (EC50 = 81.8 +/- 8.7 mu M). The 6-OH-5,7-dimethoxy analogue (+/-)-3d showed significant inhibition of xanthine oxidase with an IC50 value of 16.0 +/- 0.8 mu M, which is superior to that of allopurinol (IC50 = 23.5 +/- 2.0 mu M). In addition to the hypothesized action mechanism of the bio-active compounds, 3D modeling was used to analyze the relationship between the minimized-energy structures and antioxidant activities. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.03.032