(1R,2S,5R)-5-methyl-1-(oxiran-2-ylmethyl)-2-propan-2-ylcyclohexan-1-ol | 1110772-49-0

• 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: (1R,2S,5R)-5-methyl-1-(oxiran-2-ylmethyl)-2-propan-2-ylcyclohexan-1-ol
• CAS: 1110772-49-0
• 化学式: C₁₃H₂₄O₂
• 分子量: 212.332
• InChiKey: KPJZMIHZEMEOSX-IBSWDFHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2S,5R)-5-methyl-1-(oxiran-2-ylmethyl)-2-propan-2-ylcyclohexan-1-ol 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以51%的产率得到(1R,3R,4S,2'R)-3-(2'-hydroxypropyl)-p-menthan-3-ol
  参考文献：
  名称：

  3-Alkyl-p-menthan-3-ol derivatives: synthesis and evaluation of their physiological cooling activity

  摘要：

  Different 3-alkyl-p-methan-3-ol derivatives provide a strong physiological cooling effect with potential application as food and cosmetic additives. In order to investigate the influence of the chemical structure on the cooling sensation, the stereoselective syntheses of 29 different 3-alkyl-p-methan-3-ol derivatives were accomplished. All the compounds obtained are odorless and were evaluated by taste, considering two sensations: a cooling effect and bitterness. The results of this structure-activity relationship study highlight that compounds with a (1R,4S)-configuration are the isomers with the more intense cooling effect and lower bitterness. In addition, the structure of the 3-alkyl chain affected the latter properties. Increasing the chain length over two carbon atoms does not change the cooling power, but enhances the bitterness with the additional feature that the branched isomers are considerably more bitter than the linear ones. Overall, the 3-alkyl-p-menthan-3-ol isomers with the best quality in terms of high cooling power and low bitterness are (1R,4S)-3-(hydroxymethyl)-p-menthan-3-ol diasteroisomers (-)-38 and (-)-42. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.10.022
• 作为产物：
  描述：

  (1S,2S,5R)-1-烯丙基-2-异丙基-5-甲基环己醇 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到(1R,2S,5R)-5-methyl-1-(oxiran-2-ylmethyl)-2-propan-2-ylcyclohexan-1-ol
  参考文献：
  名称：

  3-Alkyl-p-menthan-3-ol derivatives: synthesis and evaluation of their physiological cooling activity

  摘要：

  Different 3-alkyl-p-methan-3-ol derivatives provide a strong physiological cooling effect with potential application as food and cosmetic additives. In order to investigate the influence of the chemical structure on the cooling sensation, the stereoselective syntheses of 29 different 3-alkyl-p-methan-3-ol derivatives were accomplished. All the compounds obtained are odorless and were evaluated by taste, considering two sensations: a cooling effect and bitterness. The results of this structure-activity relationship study highlight that compounds with a (1R,4S)-configuration are the isomers with the more intense cooling effect and lower bitterness. In addition, the structure of the 3-alkyl chain affected the latter properties. Increasing the chain length over two carbon atoms does not change the cooling power, but enhances the bitterness with the additional feature that the branched isomers are considerably more bitter than the linear ones. Overall, the 3-alkyl-p-menthan-3-ol isomers with the best quality in terms of high cooling power and low bitterness are (1R,4S)-3-(hydroxymethyl)-p-menthan-3-ol diasteroisomers (-)-38 and (-)-42. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.10.022