(+)-menthyl dodecanoate | 161275-87-2

• 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 dodecanoate
• 英文别名: (-) menthyl laurate；lauric acid (1S,2R,5S)-menthyl ester；[(1S,2R,5S)-5-methyl-2-propan-2-ylcyclohexyl] dodecanoate
• CAS: 161275-87-2
• 化学式: C₂₂H₄₂O₂
• 分子量: 338.574
• InChiKey: DKFFWVHIJZJJCM-HBMCJLEFSA-N

物化性质

• 沸点：
  379.1±10.0 °C(Predicted)
• 密度：
  0.89±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  24
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+)-menthyl dodecanoate 在 水 作用下， 以 异辛烷 为溶剂， 生成 月桂酸 、 D-薄荷醇
  参考文献：
  名称：

  Quantitative analyses of biochemical kinetic resolution of enantiomers. 2. Enzyme-catalyzed esterifications in water-organic solvent biphasic systems

  摘要：

  DOI：

  10.1021/ja00243a040
• 作为产物：
  描述：

  月桂酸 在 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 (+)-menthyl dodecanoate
  参考文献：
  名称：

  d-薄荷醇脂肪酸酯衍生物及其应用和制备方法

  摘要：

  本发明属于医药技术领域，涉及一种d‑薄荷醇脂肪酸酯衍生物及其应用和制备方法。所述的d‑萜品醇脂肪酸酯是由d‑薄荷醇与直链脂肪酸经酯化反应而得到的。方法是首先脂肪酸与氯化亚砜反应制备酰氯，然后酰氯与d‑薄荷醇反应制备成酯而得到的。d‑薄荷醇酯作为促透剂应用于贴剂、巴布剂、软膏剂、凝胶剂、喷雾剂、搽剂外用制剂，从而提高药物特别是手性药物对映体的经皮吸收量，是一种很好的经皮吸收促透剂，具有广阔的应用前景。

  公开号：

  CN106631789A

文献信息

• Lipase catalyzed reactions and strategy for alcohol resolution
  作者：Georges Langrand、Jacques Baratti、Gérard Buono、Christian Triantaphylides

  DOI：10.1016/s0040-4039(00)83931-3

  日期：1986.1

  hydrolysis, ester interchange and ester formation were carried out for menthol resolution with Candida cylindracea lipase. The reactions were realized under emulsified conditions with water soluble enzyme and in organic medium with an insoluble enzyme preparation. In the latter case, an enhancement of the enantioselectivity uas observed. The potentialities of ester interchange and ester formation for

  用假丝酵母念珠菌脂肪酶进行不对称水解，酯交换和酯形成以用于薄荷醇拆分。该反应是在乳化条件下用水溶性酶和在有机介质中用不溶酶制剂实现的。在后一种情况下，观察到对映选择性的增强。讨论了酯交换和酯形成用于制备醇的拆分反应的潜力。
• Candida rugosa lipase: Enantioselectivity enhancements in organic solvents
  作者：Rose A. Persichetti、Jim J. Lalonde、Chandrika P. Govardhan、Nazer K. Khalaf、Alexey L. Margolin

  DOI：10.1016/0040-4039(96)01430-x

  日期：1996.9

  Chiral resolutions of carboxylic acids (1-3) and alcohol (4) were carried out through esterification or transesterification in organic solvents using cross-linked enzyme crystals (CLEC(R)) of Candida rugosa lipase (CRL). Comparison of these results with those of elude CRL reveal significant differences. As was seen in resolution through hydrolysis,(1) a marked improvement in enantioselectivity is realized with the CLEC. Additionally, the stability afforded the enzyme in CLEC form leads to a higher activity in organic solvent. Copyright (C) 1996 Elsevier Science Ltd
• Thermodynamics of the Lipase-Catalyzed Esterification of 1-Dodecanoic Acid with (−)-Menthol in Organic Solvents
  作者：Yadu B. Tewari、Michele M. Schantz、David J. Vanderah

  DOI：10.1021/je980299p

  日期：1999.5.1

  The thermodynamics of the lipase-catalyzed stereospecific esterification of 1-dodecanoic acid with (-)-menthol in seven organic solvents have been investigated. Equilibrium measurements were performed using hexane, heptane, cyclohexane, toluene, 2,2,4-trimethylpentane, acetonitrile, and 2-methyl-2-butanol at the temperature T = 298.15 K. The equilibrium constants have been correlated with the (octanol + water) partition coefficients and the relative permittivities of the solvents. The saturation molalities and the (hexane + water) partition coefficients of (-)-menthol, 1-dodecanoic acid, and (-)-menthyl dodecanoate have also been determined at T = 298.15 K. The equilibrium constant of the esterification reaction in aqueous media has been calculated. An important finding is that the molality of water plays an important role in determining the extent of ester formation. Tn acetonitrile and 2-methyl-2-butanol, which have a very high molality of water, the formation of (-)-menthyl dodecanoate is considerably smaller. However, in hydrophobic solvents with lower molalities of water, the formation of (-)-menthyl dodecanoate is favored in the reaction mixture. The value of the equilibrium constant varies from 3 to 26. However, the molality of (-)-menthyl dodecanoate changes from 0.034 mmol kg(-1) in acetonitrile to 16 mmol kg(-1) in heptane. The change in product yield is a factor of approximate to 500 and is a striking example of the utility of organic solvents in biocatalysis.
• Enzymatic esterification of (−)-menthol with lauric acid in isooctane by sorbitan monostearate-coated lipase from Candida rugosa
  作者：Banu Babali、Melek Tuter、Guldem Ustun

  DOI：10.1007/s11746-001-0239-6

  日期：2001.2

  AbstractEsterification of (−)‐menthol and (±)‐menthol with lauric acid in isooctane was successfully catalyzed by a commercial nonioic surfactant (sorbitan monosterate)‐coated lipase from Candida rugosa (Lipase AY “Amano” 30) at the molar ratio of 1∶1 and at 35°C using 1.5 g enzyme/g (−)‐menthol and 0.1‐g molecular sieves. After 1 h, molar conversion of (−)‐menthol reached 81%. Equilibrium was reached after ca. 4 h, giving a (−)‐menthol molar conversion of 94%. Under the same conditions, native lipase catalyzed the esterification of (−)‐menthol and lauric acid to yield a molar conversion of 93% after 72 h. Coating the lipase with sorbitan monosterate increased the esterification rates of both (−)‐menthol and (±)‐menthol with lauric acid. After 6 h, the molar conversions of (−)‐menthol and (±)‐menthol were 94, and 62%, respectively.