5-(1,2-dihydroxy-1-methylethyl)-2-methyl-2-cyclohexen-1-one | 81679-70-1

• 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: 5-(1,2-dihydroxy-1-methylethyl)-2-methyl-2-cyclohexen-1-one
• 英文别名: rac-8,9-dihydroxy-p-menth-6-en-2-one；uroterpenolone；5-(1,2-Dihydroxypropan-2-yl)-2-methylcyclohex-2-en-1-one；5-(1,2-dihydroxypropan-2-yl)-2-methylcyclohex-2-en-1-one
• CAS: 81679-70-1
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: AOKPDATZUBLDMG-UHFFFAOYSA-N

物化性质

• 沸点：
  348.5±30.0 °C(Predicted)
• 密度：
  1.158±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(1,2-dihydroxy-1-methylethyl)-2-methyl-2-cyclohexen-1-one 在 sodium periodate 作用下， 以 甲醇 为溶剂， 反应 0.67h， 以82%的产率得到5-acetyl-2-methyl-2-cyclohexen-1-one
  参考文献：
  名称：

  Detection of a “Nonaromatic” NIH Shift during In Vivo Metabolism of the Monoterpene Carvone in Humans

  摘要：

  High-resolution gas chromatography in combination with mass spectrometry and high-resolution mass spectrometry was used to determine the positions and extent of labeling in the metabolites of carvone, namely in alpha,4-dimethyl-5-oxo-3-cyclohexene-1-acetic acid (dihydrocarvonic acid), (alpha-methylene-4methyl-5-oxo-3-cyclohexene-1 -acetic acid (carvonic acid), and 5-(1,2-dihydroxy-l-methylethyl)-2methyl-2-cyclohexen-1 -one (uroterpenolone), after human ingestion of 9,9-dideutero- and 9-(13)-C-carvone. Carvonic acid was formed by oxidation at the methyl carbon of the isopropenyl group of carvone, whereas dihydrocarvonic acid was formed by oxidation at the methylene position, most probably via carvone epoxide. A "nonaromatic" NIH shift must occur during the subsequent reactions yielding dihydrocarvonic acid. Additionally, dehydrogenation of dihydrocarvonic acid and hydrogenation of carvonic acid were observed, resulting in minor amounts of both acids owning a carboxy group of opposite origin. Uroterpenolone was found to be exclusively formed by oxidation at the methylene carbon of the isopropenyl group of carvone, and thus, most probably by hydrolysis of carvone epoxide.

  DOI：

  10.1021/jf011199h
• 作为产物：
  描述：

  carvone oxide 在 硫酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以81%的产率得到5-(1,2-dihydroxy-1-methylethyl)-2-methyl-2-cyclohexen-1-one
  参考文献：
  名称：

  使用摄入相关量代谢（MICA）方法对人体内单萜S-（+）-和R-（-）-香芹酮代谢的体内研究。

  摘要：

  摄入相关量代谢试验（MICA）中S-（+）-和R-（-）-香芹酮的主要体内代谢物新近被鉴定为α，4-二甲基-5-氧代-3-氧代-3-环己烯-1 -乙酸（二氢香芹酸），α-亚甲基-4-甲基-5-氧代-3-环己烯-1-乙酸（香芹酸）和5-（1,2-二羟基-1-甲基乙基）-2-质谱分析结合合成和NMR实验的基础上，对甲基-2-环己烯-1-酮（尿萜烯酮）进行了分析。少量代谢物被鉴定为香芹酮的还原产物，即醇香芹酚和二氢香芹酚。无法检测到兔子先前确定的主要体内代谢产物10-羟基香芹酮，表明浓度影响或种间差异。讨论了人类中香芹酮的代谢途径，包括侧链中双键的氧化以及小范围的1,2-和1,4 + 1,2-还原。没有检测到S-（+）-和R-（-）-香芹酮之间的代谢差异。

  DOI：

  10.1021/jf010157q

文献信息

• Monoterpenoid chemistry. Part 3.. Stereoselective synthesis of the major oxygenated metabolites oftrans-sobrerol
  作者：Renato Pellegata、Ivana Dosi、Paolo Ventura、Maurizio Villa、Giordano Lesma、Giovanni Palmisano

  DOI：10.1002/hlca.19870700109

  日期：1987.2.4

  The stereoselective synthesis of the major oxygenated metabolites of trans-sobrerol (1) in optically active and/or racemic form is described.

  描述了光学活性和/或外消旋形式的反式-sobrerol（1）的主要氧化代谢物的立体选择性合成。
• In Vivo Studies on the Metabolism of the Monoterpenes <i>S</i>-(+)- and <i>R</i>-(−)-Carvone in Humans Using the Metabolism of Ingestion-Correlated Amounts (MICA) Approach
  作者：Wolfgang Engel

  DOI：10.1021/jf010157q

  日期：2001.8.1

  The major in vivo metabolites of S-(+)- and R-(-)-carvone in a metabolism of ingestion correlated amounts (MICA) experiment were newly identified as alpha,4-dimethyl-5-oxo-3-cyclohexene-1-acetic acid (dihydrocarvonic acid), alpha-methylene-4-methyl-5-oxo-3-cyclohexene-1-acetic acid (carvonic acid), and 5-(1,2-dihydroxy-1-methylethyl)-2-methyl-2-cyclohexen-1-one (uroterpenolone) on the basis of mass

  摄入相关量代谢试验（MICA）中S-（+）-和R-（-）-香芹酮的主要体内代谢物新近被鉴定为α，4-二甲基-5-氧代-3-氧代-3-环己烯-1 -乙酸（二氢香芹酸），α-亚甲基-4-甲基-5-氧代-3-环己烯-1-乙酸（香芹酸）和5-（1,2-二羟基-1-甲基乙基）-2-质谱分析结合合成和NMR实验的基础上，对甲基-2-环己烯-1-酮（尿萜烯酮）进行了分析。少量代谢物被鉴定为香芹酮的还原产物，即醇香芹酚和二氢香芹酚。无法检测到兔子先前确定的主要体内代谢产物10-羟基香芹酮，表明浓度影响或种间差异。讨论了人类中香芹酮的代谢途径，包括侧链中双键的氧化以及小范围的1,2-和1,4 + 1,2-还原。没有检测到S-（+）-和R-（-）-香芹酮之间的代谢差异。
• Detection of a “Nonaromatic” NIH Shift during In Vivo Metabolism of the Monoterpene Carvone in Humans
  作者：Wolfgang Engel

  DOI：10.1021/jf011199h

  日期：2002.3.1

  High-resolution gas chromatography in combination with mass spectrometry and high-resolution mass spectrometry was used to determine the positions and extent of labeling in the metabolites of carvone, namely in alpha,4-dimethyl-5-oxo-3-cyclohexene-1-acetic acid (dihydrocarvonic acid), (alpha-methylene-4methyl-5-oxo-3-cyclohexene-1 -acetic acid (carvonic acid), and 5-(1,2-dihydroxy-l-methylethyl)-2methyl-2-cyclohexen-1 -one (uroterpenolone), after human ingestion of 9,9-dideutero- and 9-(13)-C-carvone. Carvonic acid was formed by oxidation at the methyl carbon of the isopropenyl group of carvone, whereas dihydrocarvonic acid was formed by oxidation at the methylene position, most probably via carvone epoxide. A "nonaromatic" NIH shift must occur during the subsequent reactions yielding dihydrocarvonic acid. Additionally, dehydrogenation of dihydrocarvonic acid and hydrogenation of carvonic acid were observed, resulting in minor amounts of both acids owning a carboxy group of opposite origin. Uroterpenolone was found to be exclusively formed by oxidation at the methylene carbon of the isopropenyl group of carvone, and thus, most probably by hydrolysis of carvone epoxide.