1'-O-ketoprofen sucroside | 1147275-60-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1'-O-ketoprofen sucroside
• CAS: 1147275-60-2
• 化学式: C₂₈H₃₄O₁₃
• 分子量: 578.57
• InChiKey: XHMSQPFVUNNNIK-LTHDRUCVSA-N

物化性质

• 沸点：
  831.9±65.0 °C(predicted)
• 密度：
  1.53±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.81
• 重原子数：
  41.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  212.67
• 氢给体数：
  7.0
• 氢受体数：
  13.0

反应信息

• 作为产物：
  描述：

  (S)-ketoprofen vinyl ester 、 蔗糖 在 吡啶 、 Bacillus licheniformis protease 作用下， 以 叔丁醇 为溶剂， 以50%的产率得到1'-O-ketoprofen sucroside
  参考文献：
  名称：

  Two-step enzymatic selective synthesis of water-soluble ketoprofen–saccharide conjugates in organic media

  摘要：

  Ketoprofen-saccharide conjugates were synthesized by selectively enzymatic hydrolysis and acylation. Firstly, the (S)-ketoprofen vinyl ester was prepared by enzymatic hydrolysis of (R, S)-ketoprofen vinyl ester. Then enzymatic transesterification of (S)-ketoprofen vinyl ester with a series of saccharides were performed by the catalysis of a commercial protease from Bacillus licheniformis (BLP) in organic medium mixture of pyridine and tert-butanol. The ketoprofen was selectively conjugated onto the primary hydroxyl group of saccharides and with high yield after 72 h. Partition coefficient determination showed that all the products have better water solubility than parent ketoprofen. Chemical hydrolysis experiment indicated that 50% ketoprofen could be release from ketoprofen glucoside and maltoside in aqueous buffer (pH 7.4) within 48 h. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.01.040