(R)-allethrolone acetate | 66513-32-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-allethrolone acetate
• 英文别名: (R)-Allethrolon-acetat；(1R)-2-Methyl-4-oxo-3-(prop-2-en-1-yl)cyclopent-2-en-1-yl acetate；[(1R)-2-methyl-4-oxo-3-prop-2-enylcyclopent-2-en-1-yl] acetate
• CAS: 66513-32-4
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: MDFPPPIHFJPKRF-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (1S)-acetoxy-2-methyl-3-allyl-4-oxo-cyclopent-2-ene 生成 (R)-allethrolone acetate 、 (S)-allethrolone acetate
  参考文献：
  名称：

  从新分离的枯草芽孢杆菌ECU0554通过高底物浓度可耐受的酯酶酶促生产1-薄荷醇

  摘要：

  Abstractmagnified imageEnzymatic preparation of l‐menthol has been attracting much attention in the flavor and fragrance industry. A new ideal strain, Bacillus subtilis ECU0554, which exhibited high hydrolytic activity and excellent enantioselectivity towards l‐menthyl ester, has been successfully isolated from soil samples through enrichment culture and identified as Bacillus subtilis by 16S rDNA gene sequencing. The esterase extracted from B. subtilis ECU0554 (BSE) showed the best catalytic properties (E>200) for dl‐menthyl acetate among the five menthyl esters examined. Enantioselective hydrolysis of 100 mM dl‐menthyl acetate at 30°C and pH 7.0, using crude BSE as biocatalyst and 10% ethanol (v/v) as cosolvent, resulted in 49.0% conversion (3 h) and 98.0% ee for the l‐menthol produced, which were much better than those using commercial enzymes tested. Moreover, BSE exhibited strong tolerance against high substrate concentration (up to 500 mM), and the concentration of l‐menthol produced could reach as high as 182 mM, and more importantly, the optical purity of l‐menthol produced was kept above 97% ee, which were not found in previous reports. These results imply that BSE is a potentially promising biocatalyst for the large‐scale enzymatic preparation of l‐menthol. Using this excellent biocatalyst, the enzymatic production of l‐menthol will become a mild, efficient, inexpensive and easy‐to‐use “green chemistry” methodology.

  DOI：

  10.1002/adsc.200800412

文献信息

• Enzyme catalyzed resolution of alcohols using ethoxyvinyl acetate
  作者：Manfred Schudok、Gerhard Kretzschmar

  DOI：10.1016/s0040-4039(96)02333-7

  日期：1997.1

  1-Ethoxyvinyl acetate is an efficient irreversible acyl transfer reagent for lipase catalyzed esterification in organic solvents. The use of this reagent avoids reactive byproducts resulting in enzyme deactivation, in particular the formation of acetaldehyde using the widely employed vinyl acetate transesterification reagent. Copyright (C) 1996 Elsevier Science
• Enzymatic Production of l-Menthol by a High Substrate Concentration Tolerable Esterase from Newly Isolated Bacillus subtilis ECU0554
  作者：Gao-Wei Zheng、Hui-Lei Yu、Jian-Dong Zhang、Jian-He Xu

  DOI：10.1002/adsc.200800412

  日期：2009.2

  Abstractmagnified imageEnzymatic preparation of l‐menthol has been attracting much attention in the flavor and fragrance industry. A new ideal strain, Bacillus subtilis ECU0554, which exhibited high hydrolytic activity and excellent enantioselectivity towards l‐menthyl ester, has been successfully isolated from soil samples through enrichment culture and identified as Bacillus subtilis by 16S rDNA gene sequencing. The esterase extracted from B. subtilis ECU0554 (BSE) showed the best catalytic properties (E>200) for dl‐menthyl acetate among the five menthyl esters examined. Enantioselective hydrolysis of 100 mM dl‐menthyl acetate at 30°C and pH 7.0, using crude BSE as biocatalyst and 10% ethanol (v/v) as cosolvent, resulted in 49.0% conversion (3 h) and 98.0% ee for the l‐menthol produced, which were much better than those using commercial enzymes tested. Moreover, BSE exhibited strong tolerance against high substrate concentration (up to 500 mM), and the concentration of l‐menthol produced could reach as high as 182 mM, and more importantly, the optical purity of l‐menthol produced was kept above 97% ee, which were not found in previous reports. These results imply that BSE is a potentially promising biocatalyst for the large‐scale enzymatic preparation of l‐menthol. Using this excellent biocatalyst, the enzymatic production of l‐menthol will become a mild, efficient, inexpensive and easy‐to‐use “green chemistry” methodology.