L-menthyl oleate | 6070-18-4

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 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: L-menthyl oleate
• 英文别名: rel-(1R,2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexyl (9Z)-9-octadecenoate；[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] (Z)-octadec-9-enoate
• CAS: 6070-18-4
• 化学式: C₂₈H₅₂O₂
• 分子量: 420.72
• InChiKey: KSXDYSUCRAXJBC-NPIJWRSCSA-N

物化性质

• 沸点：
  490.5±24.0 °C(Predicted)
• 密度：
  0.90±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.1
• 重原子数：
  30
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  油酸 、 L-薄荷醇 在 磷脂酶B 作用下， 以 水 为溶剂， 反应 24.0h， 以96%的产率得到L-menthyl oleate
  参考文献：
  名称：

  Enzymatic synthesis of l-menthyl esters in organic solvent-free system

  摘要：

  Abstractl‐Menthol has been widely used as a food additive and an ingredient of cosmetics, and it is esterified to moderate the strong flavor. We attempted esterification of l‐menthol with long‐chain unsaturated fatty acid in an organic solvent‐free enzymatic system. Commercially available lipases were screened, and Candida rugosa lipase was selected as a catalyst. Several factors affecting the esterification were investigated, and the reaction conditions were determined as follows: A reaction mixture of l‐menthol/fatty acid (1:3, mol/mol), 30% water, and 700 units of the lipase per gram of reaction mixture was incubated at 30°C with stirring. After 24 h under these conditions, the esterification extents of l‐menthol with oleic, linoleic, and α‐linolenic acids reached 96, 88, and 95%, respectively. The structure of the esterified product was confirmed by mass, infrared, and nuclear magnetic resonance spectroscopies. Bacause Candida lipase acted strongly on l‐menthol and very weakly on d‐menthol, dl‐menthol was esterified with oleic acid under the same conditions. The reaction showed high enantioselectivity; the enantiomeric ratio (E) was 31, and enantiomeric excess (ee) of l‐menthyl oleate reached 88% after 32 h.

  DOI：

  10.1007/s11746-999-0086-3

文献信息

• Enzymatic esterification of (−)-menthol with fatty acids in solvent by a commercial lipase from <i>Candida rugosa</i>
  作者：Banu Babali、H. Ay§e Aksoy、Melek Tüter、Guldem Ustun

  DOI：10.1007/s11746-001-0219-x

  日期：2001.1

  AbstractEsterification of (−)‐menthol with fatty acids in isooctane was successfully catalyzed using a commercial lipase, Lipase AY “Amano” 30 from Candida rugosa in original powder form. The esterification reactions were performed to elucidate the effects of temperature, enzyme load, molar ratio of (−)‐menthol/fatty acid, and fatty acid type, keeping the (−)‐menthol concentration at 200 mM. At the optimal conditions for (−)‐menthol esterification, determined at a (−)‐menthol/lauric acid molar ratio of 1∶1 and 35°C [1.5 g enzyme/g (−)‐menthol, 0.1 g molecular sieves], the molar conversion of (−)‐menthol after 48 h reached 93%. After 24h, the lowest and the highest molar conversions of fatty acids at 2∶1 molar ratio were obtained with myristic acid (71%) and margaric acid (98%), respectively. After 48 h, the molar conversions of lauric acid at molar ratios 2∶1, 1∶1, and 1∶2 were 98, 93, and 49%, respectively.