menthyl octanoate | 93940-59-1

• 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: menthyl octanoate
• 英文别名: rel-(1R,2S,5R)-5-Ethyl-2-(1-methylethyl)cyclohexyl octanoate；[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] octanoate
• CAS: 93940-59-1
• 化学式: C₁₈H₃₄O₂
• 分子量: 282.467
• InChiKey: YBENVMAMNHOPRF-IXDOHACOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  辛酸 、 L-薄荷醇 在 hog pancreas lipase 作用下， 以 甲苯 为溶剂， 生成 menthyl octanoate
  参考文献：
  名称：

  Biocatalytic enantiomeric resolution of l-menthol from an eight isomeric menthol mixture through transesterification

  摘要：

  The four diastereomers of menthol and their enantiomers, namely DL-menthol, DL-neomenthol, DL-neoisomenthol and DL-isomenthol, were synthesised by the hydrogenation of thymol to yield an eight isomer liquid menthol. A suitably selective lipase was sought to preferentially esterify L-menthol in organic solvent, hence simplifying separation from the diasteromeric mix through distillation. From an initial screen a commercial Pseudomonas fluorescens lipase (Amano AK) was selected, and vinyl acetate was chosen as a suitable irreversible acyl donor for transesterification. The reaction reagent ratios were optimised, and an enantiomeric excess (ee) of L-menthol of greater than 95% was reproducibly achievable at a conversion of 30% DL-menthol (0.68 M) at <= 50 degrees C. On the basis of the composition of liquid menthol the reaction had a diastereomeric excess (de) of 82%. The enzyme was recycled 150 times in 5 ml batch reactions using liquid menthol and achieving an overall yield of 184.3 g DL-menthol/g commercial enzyme preparation. The by-product acetic acid, formed by hydrolysis of menthyl acetate, was found to cause a high degree of enzyme inactivation.The resolution reaction was scaled up 400 fold to 2 L and the enzyme recycled 38 times with an average conversion of the available L-menthol of 59% and a volumetric productivity of 1.2 g/L/h. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2011.10.011

文献信息

• Biocatalytic enantiomeric resolution of l-menthol from an eight isomeric menthol mixture through transesterification
  作者：D. Brady、S. Reddy、B. Mboniswa、L.H. Steenkamp、A.L. Rousseau、C.J. Parkinson、J. Chaplin、R.K. Mitra、T. Moutlana、S.F. Marais、N.S. Gardiner

  DOI：10.1016/j.molcatb.2011.10.011

  日期：2012.3

  The four diastereomers of menthol and their enantiomers, namely DL-menthol, DL-neomenthol, DL-neoisomenthol and DL-isomenthol, were synthesised by the hydrogenation of thymol to yield an eight isomer liquid menthol. A suitably selective lipase was sought to preferentially esterify L-menthol in organic solvent, hence simplifying separation from the diasteromeric mix through distillation. From an initial screen a commercial Pseudomonas fluorescens lipase (Amano AK) was selected, and vinyl acetate was chosen as a suitable irreversible acyl donor for transesterification. The reaction reagent ratios were optimised, and an enantiomeric excess (ee) of L-menthol of greater than 95% was reproducibly achievable at a conversion of 30% DL-menthol (0.68 M) at <= 50 degrees C. On the basis of the composition of liquid menthol the reaction had a diastereomeric excess (de) of 82%. The enzyme was recycled 150 times in 5 ml batch reactions using liquid menthol and achieving an overall yield of 184.3 g DL-menthol/g commercial enzyme preparation. The by-product acetic acid, formed by hydrolysis of menthyl acetate, was found to cause a high degree of enzyme inactivation.The resolution reaction was scaled up 400 fold to 2 L and the enzyme recycled 38 times with an average conversion of the available L-menthol of 59% and a volumetric productivity of 1.2 g/L/h. (C) 2011 Elsevier B.V. All rights reserved.