(E)-3-[5-(1,2-dimethyl-2-propenyl)-4-hydroxy-3-methoxyphenyl]-1-(2,4,6-trihydroxyphenyl)-2-propen-1-one | 1412939-09-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-3-[5-(1,2-dimethyl-2-propenyl)-4-hydroxy-3-methoxyphenyl]-1-(2,4,6-trihydroxyphenyl)-2-propen-1-one
• 英文别名: HMT；(e)-3-[5-(1,2-Dimethyl-2-propenyl)-4-hydroxy-3-methoxyphenyl]-1-(2,4,6-trihydroxyphenyl)-2-propen-1-one；(E)-3-[4-hydroxy-3-methoxy-5-(3-methylbut-3-en-2-yl)phenyl]-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one
• CAS: 1412939-09-3
• 化学式: C₂₁H₂₂O₆
• 分子量: 370.402
• InChiKey: XDMNEUBJCSHYRB-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-甲氧基-4-[(3-甲基-2-丁烯-1-基)氧基]苯甲醛 在 盐酸 、 水 、 potassium carbonate 、 N,N-二甲基苯胺 、 potassium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 、 丙酮 为溶剂， 反应 38.0h， 生成 (E)-3-[5-(1,2-dimethyl-2-propenyl)-4-hydroxy-3-methoxyphenyl]-1-(2,4,6-trihydroxyphenyl)-2-propen-1-one
  参考文献：
  名称：

  Synthesis of licochalcones and inhibition effects on radical-induced oxidation of DNA

  摘要：

  This study deals with the influence of phenolic hydroxyl groups on the antioxidant capacities of licochalcones. (E)-3-[5-(1,2-Dimethyl-2-propenyl)-4-hydroxy-3-methoxyphenyl]-1-(4-hydroxyphenyl)-2-propen-1-one (HMP), (E)-3-[5-(1,2-dimethyl-2-propenyl)-4-hydroxy-3-methoxyphenyl]-1-(2,4-dihydroxyphenyl)-2-propen-1-one (DHM), and (E)-3-[5-(1,2-dimethyl-2-propenyl)-4-hydroxy-3-methoxyphenyl]-1-(2,4,6-trihydroxyphenyl)-2-propen-1-one (HMT) were synthesized via abnormal Claisen rearrangement and Claisen-Schmidt condensation. The antioxidant capacities were evaluated in hydroxyl radical ((OH)-O-aEuro cent)-, Cu2+/glutathione (GSH)-, and 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH)-induced oxidation of DNA. It was found that only HMP possessed weak ability to inhibit (OH)-O-aEuro cent-induced oxidation of DNA, and DHM and HMT cannot protect DNA against the oxidation. All the licochalcones employed herein can retard Cu2+/GSH-induced oxidation of DNA, the activity followed the order of HMP > DHM > HMT. Hence, more hydroxyl groups did not ameliorate the antioxidant effectiveness in the aforementioned experimental systems. On the other hand, HMT, DHM, and HMP can scavenge 5.61, 2.42, and 1.68 radicals, respectively, when they were applied to protect DNA against AAPH-induced oxidation. This result demonstrated that more hydroxyl groups enhanced the antioxidant capacities of licochalcones in this case. The obtained information was beneficial for designing novel licochalcones.Effects on (OH)-O-aEuro cent-, Cu2+/glutathione-, and AAPH-induced oxidation of DNA.

  DOI：

  10.1007/s00044-012-0282-9

文献信息

• Synthesis of licochalcones and inhibition effects on radical-induced oxidation of DNA
  作者：Jianghua He、Jizhen Li、Zai-Qun Liu

  DOI：10.1007/s00044-012-0282-9

  日期：2013.6

  This study deals with the influence of phenolic hydroxyl groups on the antioxidant capacities of licochalcones. (E)-3-[5-(1,2-Dimethyl-2-propenyl)-4-hydroxy-3-methoxyphenyl]-1-(4-hydroxyphenyl)-2-propen-1-one (HMP), (E)-3-[5-(1,2-dimethyl-2-propenyl)-4-hydroxy-3-methoxyphenyl]-1-(2,4-dihydroxyphenyl)-2-propen-1-one (DHM), and (E)-3-[5-(1,2-dimethyl-2-propenyl)-4-hydroxy-3-methoxyphenyl]-1-(2,4,6-trihydroxyphenyl)-2-propen-1-one (HMT) were synthesized via abnormal Claisen rearrangement and Claisen-Schmidt condensation. The antioxidant capacities were evaluated in hydroxyl radical ((OH)-O-aEuro cent)-, Cu2+/glutathione (GSH)-, and 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH)-induced oxidation of DNA. It was found that only HMP possessed weak ability to inhibit (OH)-O-aEuro cent-induced oxidation of DNA, and DHM and HMT cannot protect DNA against the oxidation. All the licochalcones employed herein can retard Cu2+/GSH-induced oxidation of DNA, the activity followed the order of HMP > DHM > HMT. Hence, more hydroxyl groups did not ameliorate the antioxidant effectiveness in the aforementioned experimental systems. On the other hand, HMT, DHM, and HMP can scavenge 5.61, 2.42, and 1.68 radicals, respectively, when they were applied to protect DNA against AAPH-induced oxidation. This result demonstrated that more hydroxyl groups enhanced the antioxidant capacities of licochalcones in this case. The obtained information was beneficial for designing novel licochalcones.Effects on (OH)-O-aEuro cent-, Cu2+/glutathione-, and AAPH-induced oxidation of DNA.