2-O-methyllatifolin | 1164356-55-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-O-methyllatifolin
• 英文别名: 2'-O-Methyllatifolin；2,4-dimethoxy-5-[(1R)-1-(2-methoxyphenyl)prop-2-enyl]phenol
• CAS: 1164356-55-1
• 化学式: C₁₈H₂₀O₄
• 分子量: 300.354
• InChiKey: AUGRADIKXWXROE-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  重氮甲烷 、 阔叶黄檀酚 以 乙醚 为溶剂， 生成 R(-)-5-O-methyllatifolin 、 O,O-Dimethyl-latifolin 、 2-O-methyllatifolin
  参考文献：
  名称：

  Bioactivity of Latifolin and Its Derivatives against Termites and Fungi

  摘要：

  Latifolin (1) and its derivatives were investigated with the aim of confirming the correlation between bioactivity (antitermite and antifungal activity) and chemical structure. Termite mortality in response to the derivatives 2'-O-methyllatifolin (2), latifolin dimethyl ether (4), and latifolin diacetate (5) increased 2-fold compared to compound 1. The mortality rate from 5-O-methyllatifolin (3) was not different from 1. The mass loss (feed consumption by termite) in response to compounds 3-5 was 3 times greater than compound 1, and the mass loss from compound 2 was twice as great as compound 1. The mortality rate from compounds 4 and 5 increased sharply 7 days after initial exposure. In assessing the antifungal activity of these compounds, it was found that the inhibition rates of white- and brown-rot fungi in response to all derivatives were less than that for compound 1. Our findings indicate that the phenolic hydroxyl group at C-5 of the A ring provides antitermite activities (mortality and mass loss). In addition, both C-5 and C-2' phenolic hydroxyl groups in the A and B rings have antifungal activity against white- and brown-rot fungi. In conclusion, the bioactivity of compound 1 depends upon the position of phenolic hydroxyl groups,

  DOI：

  10.1021/jf900719p

文献信息

• Bioactivity of Latifolin and Its Derivatives against Termites and Fungi
  作者：Nobuhiro Sekine、Tatsuya Ashitani、Tetsuya Murayama、Sakae Shibutani、Satoshi Hattori、Koetsu Takahashi

  DOI：10.1021/jf900719p

  日期：2009.7.8

  Latifolin (1) and its derivatives were investigated with the aim of confirming the correlation between bioactivity (antitermite and antifungal activity) and chemical structure. Termite mortality in response to the derivatives 2'-O-methyllatifolin (2), latifolin dimethyl ether (4), and latifolin diacetate (5) increased 2-fold compared to compound 1. The mortality rate from 5-O-methyllatifolin (3) was not different from 1. The mass loss (feed consumption by termite) in response to compounds 3-5 was 3 times greater than compound 1, and the mass loss from compound 2 was twice as great as compound 1. The mortality rate from compounds 4 and 5 increased sharply 7 days after initial exposure. In assessing the antifungal activity of these compounds, it was found that the inhibition rates of white- and brown-rot fungi in response to all derivatives were less than that for compound 1. Our findings indicate that the phenolic hydroxyl group at C-5 of the A ring provides antitermite activities (mortality and mass loss). In addition, both C-5 and C-2' phenolic hydroxyl groups in the A and B rings have antifungal activity against white- and brown-rot fungi. In conclusion, the bioactivity of compound 1 depends upon the position of phenolic hydroxyl groups,