(+)-(4S)-4-hydroxyisopiperitenone | 203452-58-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (+)-(4S)-4-hydroxyisopiperitenone
• 英文别名: 2-Cyclohexen-1-one, 6-hydroxy-3-methyl-6-(1-methylethenyl)-, (6S)-；(6S)-6-hydroxy-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-one
• CAS: 203452-58-8
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: PHAVIMQABDNJRU-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+)-(4S)-4-hydroxyisopiperitenone 在 palladium on activated charcoal 氢气 作用下， 以 正己烷 为溶剂， 反应 12.0h， 生成 (4S)-4-hydroxymenthone
  参考文献：
  名称：

  Modified Monoterpenes from Biotransformation of (−)-Isopiperitenone by Suspension Cell Culture of Mentha piperita

  摘要：

  The biotransformation of (-)-(4R)-isopiperitenone (1) by suspension cell culture of Mentha piperita yielded three new hydroxylated derivatives, 4-6, and two new epoxidized derivatives, 7 and 8. (-)-7-Hydroxyisopiperitenone (2) and its glucoside were previously isolated from the culture. The structures of 4-8 were elucidated using spectral methods, and their absolute stereochemistry was established by NMR experiments and correlation with compounds of known configuration.

  DOI：

  10.1021/np970388k
• 作为产物：
  描述：

  (-)-isopiperitenone 、 alkaline earth salt of/the/ methylsulfuric acid 在 suspension cell culture of Mentha piperita L 2,4-D 作用下， 反应 48.0h， 以7 mg的产率得到(+)-(4S)-4-hydroxyisopiperitenone
  参考文献：
  名称：

  Modified Monoterpenes from Biotransformation of (−)-Isopiperitenone by Suspension Cell Culture of Mentha piperita

  摘要：

  The biotransformation of (-)-(4R)-isopiperitenone (1) by suspension cell culture of Mentha piperita yielded three new hydroxylated derivatives, 4-6, and two new epoxidized derivatives, 7 and 8. (-)-7-Hydroxyisopiperitenone (2) and its glucoside were previously isolated from the culture. The structures of 4-8 were elucidated using spectral methods, and their absolute stereochemistry was established by NMR experiments and correlation with compounds of known configuration.

  DOI：

  10.1021/np970388k

文献信息

• Modified Monoterpenes from Biotransformation of (−)-Isopiperitenone by Suspension Cell Culture of <i>Mentha piperita</i>
  作者：Si-Hyung Park、Soo-Un Kim

  DOI：10.1021/np970388k

  日期：1998.3.1

  The biotransformation of (-)-(4R)-isopiperitenone (1) by suspension cell culture of Mentha piperita yielded three new hydroxylated derivatives, 4-6, and two new epoxidized derivatives, 7 and 8. (-)-7-Hydroxyisopiperitenone (2) and its glucoside were previously isolated from the culture. The structures of 4-8 were elucidated using spectral methods, and their absolute stereochemistry was established by NMR experiments and correlation with compounds of known configuration.