acetic acid [2-(4-methyl-2-oxocyclohexyl)propyl] ester | 623531-69-1

• 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: acetic acid [2-(4-methyl-2-oxocyclohexyl)propyl] ester
• 英文别名: 9-acetoxy-p-menthan-3-one；2-(4-methyl-2-oxocyclohexyl)propyl acetate
• CAS: 623531-69-1
• 化学式: C₁₂H₂₀O₃
• 分子量: 212.289
• InChiKey: PEOCACVMLVSVBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  acetic acid [2-(4-methyl-2-oxocyclohexyl)propyl] ester 在 lithium methanolate 作用下， 以 甲醇 为溶剂， 生成 2,3,3a,4,5,6-hexahydro-3,6-dimethylbenzofuran 、 2,3,4,5,6,7-hexahydro-3,6-dimethylbenzofuran 、 2-(2-hydroxy-1-methylethyl)-5-methylcyclohexanone
  参考文献：
  名称：

  In Vivo Studies on the Metabolism of the Monoterpene Pulegone in Humans Using the Metabolism of Ingestion-Correlated Amounts (MICA) Approach:  Explanation for the Toxicity Differences between (S)-(−)- and (R)-(+)-Pulegone

  摘要：

  The major in vivo metabolites of (S)-(-)-pulegone in humans using a metabolism of ingestion-correlated amounts (MICA) experiment were newly identified as 2-(2-hydroxy-1-methylethyl)-5methylcyclohexanone (8-hydroxymenthone, M1), 3-hydroxy-3-methyl-6-(1-methylethyl)cyclohexanone (1-hydroxymenthone, M2), 3-methyl-6-(1-methylethyl)cyclohexanol (menthol), and E-2-(2-hydroxy-1-methylethylidene)-5-methylcyclohexanone (10-hydroxypulegone, M4) on the basis of mass spectrometric analysis in combination with syntheses and NMR experiments. Minor metabolites were be identified as 3-methyl-6-(1-methylethyl)-2-cyclohexenone (piperitone, M5) and alpha,alpha,4-trimethyl-1-cyclohexene-1-methanol (3-p-menthen-8-ol, M6). Menthofuran was not a major metabolite of pulegone and is most probably an artifact formed during workup from known (M4) and/or unknown precursors. The differences in toxicity between (S)-(-)- and (R)-(+)-pulegone can be explained by the strongly diminished ability for enzymatic reduction of the double bond in (R)-(+)-pulegone. This might lead to further oxidative metabolism of 10-hydroxypulegone (M4) and the formation of further currently undetected metabolites that might account for the observed hepatotoxic and pneumotoxic activity in humans.

  DOI：

  10.1021/jf034702u
• 作为产物：
  描述：

  acetic acid [2-hydroxy-β,4-dimethylcyclohexaneethanol] ester 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 以134 mg的产率得到acetic acid [2-(4-methyl-2-oxocyclohexyl)propyl] ester
  参考文献：
  名称：

  In Vivo Studies on the Metabolism of the Monoterpene Pulegone in Humans Using the Metabolism of Ingestion-Correlated Amounts (MICA) Approach:  Explanation for the Toxicity Differences between (S)-(−)- and (R)-(+)-Pulegone

  摘要：

  The major in vivo metabolites of (S)-(-)-pulegone in humans using a metabolism of ingestion-correlated amounts (MICA) experiment were newly identified as 2-(2-hydroxy-1-methylethyl)-5methylcyclohexanone (8-hydroxymenthone, M1), 3-hydroxy-3-methyl-6-(1-methylethyl)cyclohexanone (1-hydroxymenthone, M2), 3-methyl-6-(1-methylethyl)cyclohexanol (menthol), and E-2-(2-hydroxy-1-methylethylidene)-5-methylcyclohexanone (10-hydroxypulegone, M4) on the basis of mass spectrometric analysis in combination with syntheses and NMR experiments. Minor metabolites were be identified as 3-methyl-6-(1-methylethyl)-2-cyclohexenone (piperitone, M5) and alpha,alpha,4-trimethyl-1-cyclohexene-1-methanol (3-p-menthen-8-ol, M6). Menthofuran was not a major metabolite of pulegone and is most probably an artifact formed during workup from known (M4) and/or unknown precursors. The differences in toxicity between (S)-(-)- and (R)-(+)-pulegone can be explained by the strongly diminished ability for enzymatic reduction of the double bond in (R)-(+)-pulegone. This might lead to further oxidative metabolism of 10-hydroxypulegone (M4) and the formation of further currently undetected metabolites that might account for the observed hepatotoxic and pneumotoxic activity in humans.

  DOI：

  10.1021/jf034702u