ibuprofen iso-butyl ester | 64622-50-0

• 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: ibuprofen iso-butyl ester
• 英文别名: ibuprofen isobutyl ester；Ibuprofen, isobutyl ester；2-methylpropyl 2-[4-(2-methylpropyl)phenyl]propanoate
• CAS: 64622-50-0
• 化学式: C₁₇H₂₆O₂
• 分子量: 262.392
• InChiKey: IZQZIVHKRMBEMV-UHFFFAOYSA-N

物化性质

• 沸点：
  332.8±11.0 °C(Predicted)
• 密度：
  0.952±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)
• 保留指数：
  1428

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 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：

  ibuprofen iso-butyl ester 在 buffer pH 7.4 作用下， 以 甲醇 、 水 为溶剂， 生成 异丁醇 、 布洛芬
  参考文献：
  名称：

  Bansal; Khar; Dubey, Pharmazie, 1994, vol. 49, # 6, p. 422 - 424

  摘要：

  DOI：
• 作为产物：
  描述：

  异丁醇 、 布洛芬 在 硫酸 作用下， 以 水 、 甲苯 为溶剂， 生成 ibuprofen iso-butyl ester
  参考文献：
  名称：

  Enantioselective resolution of racemic ibuprofen esters using different lipases immobilized on octyl sepharose

  摘要：

  Here we report the stereoselective hydrolysis of racemic esters catalyzed by Candida rugosa lipase (CRL) and Rhizopus oryzae lipase (ROL) immobilized on octyl-sepharose via physical adsorption. Hydrophobic immobilization caused to almost six fold hyperactivation with 229.2 and 81.3 U/mg enzyme for immobilized CRL and ROL, respectively (13.2 and 48.75 U/mg for corresponding free enzyme). Based on the preliminary results, CRL was chosen for further investigation. The performance and yield of the reaction were evaluated as a function of the critical reaction parameters such as temperature, enzyme to substrate ratio and organic co-solvent. An increase in the temperature resulted to decrease in enantioselectivity of hydrolysis reaction. The hydrolysis reactions were carried out in presence of two organic solvents; n-hexane and isooctane. Generally n-hexane was a better co-solvent compared to isooctane. High enantioselective hydrolysis of the racemic esters (yielding S(+) ibuprofen; ee >= 95%) can be achieved using the immobilized CRL. Among various esters the kinetic resolution of ibuprofen butyl ester yielded the best results (E value 70 and 74; conversion 14.6 and 8.9 in n-hexane and isooctane, respectively). The immobilized derivatives were re-used in four cycles and showed little decrease in enantiomeric excess of (S)-ibuprofen. 96.7 ee(p) and conversion 14.6 in first cycle reached to 90.5 ee(p) and conversion 11.3 in the forth cycle. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2014.03.005

文献信息

• Bansal; Khar; Dubey, Pharmazie, 1994, vol. 49, # 6, p. 422 - 424
  作者：Bansal、Khar、Dubey、Sharma

  DOI：——

  日期：——
• Enantioselective resolution of racemic ibuprofen esters using different lipases immobilized on octyl sepharose
  作者：Maryam Yousefi、Mehdi Mohammadi、Zohreh Habibi

  DOI：10.1016/j.molcatb.2014.03.005

  日期：2014.6

  Here we report the stereoselective hydrolysis of racemic esters catalyzed by Candida rugosa lipase (CRL) and Rhizopus oryzae lipase (ROL) immobilized on octyl-sepharose via physical adsorption. Hydrophobic immobilization caused to almost six fold hyperactivation with 229.2 and 81.3 U/mg enzyme for immobilized CRL and ROL, respectively (13.2 and 48.75 U/mg for corresponding free enzyme). Based on the preliminary results, CRL was chosen for further investigation. The performance and yield of the reaction were evaluated as a function of the critical reaction parameters such as temperature, enzyme to substrate ratio and organic co-solvent. An increase in the temperature resulted to decrease in enantioselectivity of hydrolysis reaction. The hydrolysis reactions were carried out in presence of two organic solvents; n-hexane and isooctane. Generally n-hexane was a better co-solvent compared to isooctane. High enantioselective hydrolysis of the racemic esters (yielding S(+) ibuprofen; ee >= 95%) can be achieved using the immobilized CRL. Among various esters the kinetic resolution of ibuprofen butyl ester yielded the best results (E value 70 and 74; conversion 14.6 and 8.9 in n-hexane and isooctane, respectively). The immobilized derivatives were re-used in four cycles and showed little decrease in enantiomeric excess of (S)-ibuprofen. 96.7 ee(p) and conversion 14.6 in first cycle reached to 90.5 ee(p) and conversion 11.3 in the forth cycle. (C) 2014 Elsevier B.V. All rights reserved.