2-xydroxycineole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 2-xydroxycineole
• 英文别名: 2-hydroxy-1,8-cineole I；(1R)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-ol
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: YVCUGZBVCHODNB-SFVIPPHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  桉叶油醇 在 phosphate buffer 、 liver microsomes of Trichosurus vulpecula 、 NADPH-generation system 作用下， 反应 10.0h， 生成 7-Hydroxycineole 、 3-xydroxycineole 、 2-xydroxycineole 、 9-xydroxycineole
  参考文献：
  名称：

  Microsomal metabolism of the terpene 1,8-cineole in the common brushtail possum (Trichosurus vulpecula), koala (Phascolarctos cinereus), rat and human

  摘要：

  1. This study reports on the pathways of metabolism and enzyme kinetics of the Eucalyptus terpene, 1,8-cineole, by liver microsomes from the brushtail possum (Trichosurus vulpecula) and koala (Phascolarctos cinereus)(animals that normally include this terpene in their diet), rat and human.2. The rank order of the ability to metabolize 1,8-cineole with respect to overall 1,8-cineole intrinsic clearance (CL'(int)= V-max/K-m in mul mg protein(-1) min(-1)) was koala (188) > possum (181) much greater than rat (28) human (12). This order supports the hypothesis that adaptation to a Eucalyptus diet involves enhanced metabolism of terpenes.3. The metabolism of 1,8-cineole was also studied in the liver from brushtail possum pretreated with a mixture of terpenes, which have previously been shown to induce cytochrome P450 enzymes. Rats were pretreated with the same mixture of terpenes or phenobarbitone.4. Terpene pretreatment more than doubled the CL'(int) of 1,8-cineole by brushtail possum liver microsomes (from 180 to 394 mul mg protein(-1) min(-1)) and increased rat CL'(int) by nearly 10-fold (from 28 to 259 mul mg protein(-1) min(-1)), but still less than the induced possum value. However, phenobarbitone had the greatest inducing effect, increasing the rat CL'(int) to 1825 mul mg protein(-1) min(-1).5. A regioselective preference of oxidation was evident between adapted and non-adapted species. In rat and human oxidation was preferred at the aliphatic ring carbons over methyl substituents. In possum, many of the available carbons were utilized, however metabolism at methyl substituents was preferred. In the koala, oxidation occurred primarily at the methyl substituents.

  DOI：

  10.1080/00498250110043535

文献信息

• Microsomal metabolism of the terpene 1,8-cineole in the common brushtail possum (<i>Trichosurus vulpecula</i>), koala (<i>Phascolarctos cinereus</i>), rat and human
  作者：G. J. Pass、S. McLean、I. Stupans、N. Davies

  DOI：10.1080/00498250110043535

  日期：2001.1

  1. This study reports on the pathways of metabolism and enzyme kinetics of the Eucalyptus terpene, 1,8-cineole, by liver microsomes from the brushtail possum (Trichosurus vulpecula) and koala (Phascolarctos cinereus)(animals that normally include this terpene in their diet), rat and human.2. The rank order of the ability to metabolize 1,8-cineole with respect to overall 1,8-cineole intrinsic clearance (CL'(int)= V-max/K-m in mul mg protein(-1) min(-1)) was koala (188) > possum (181) much greater than rat (28) human (12). This order supports the hypothesis that adaptation to a Eucalyptus diet involves enhanced metabolism of terpenes.3. The metabolism of 1,8-cineole was also studied in the liver from brushtail possum pretreated with a mixture of terpenes, which have previously been shown to induce cytochrome P450 enzymes. Rats were pretreated with the same mixture of terpenes or phenobarbitone.4. Terpene pretreatment more than doubled the CL'(int) of 1,8-cineole by brushtail possum liver microsomes (from 180 to 394 mul mg protein(-1) min(-1)) and increased rat CL'(int) by nearly 10-fold (from 28 to 259 mul mg protein(-1) min(-1)), but still less than the induced possum value. However, phenobarbitone had the greatest inducing effect, increasing the rat CL'(int) to 1825 mul mg protein(-1) min(-1).5. A regioselective preference of oxidation was evident between adapted and non-adapted species. In rat and human oxidation was preferred at the aliphatic ring carbons over methyl substituents. In possum, many of the available carbons were utilized, however metabolism at methyl substituents was preferred. In the koala, oxidation occurred primarily at the methyl substituents.