(2S)-6''-O-acetylprunin | 252324-55-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: (2S)-6''-O-acetylprunin
• 英文别名: prunin 6''-O-acetate
• CAS: 252324-55-3
• 化学式: C₂₃H₂₄O₁₁
• 分子量: 476.437
• InChiKey: WOWQBWNVGFBXQH-FPKZUJDXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.55
• 重原子数：
  34.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  172.21
• 氢给体数：
  5.0
• 氢受体数：
  11.0

反应信息

• 作为产物：
  描述：

  乙酸乙烯酯 、 柚(苷)配基-7-O-葡糖苷 在 Candida antarctica lipase B immobilized on acrylic resin 作用下， 以 丙酮 为溶剂， 反应 24.0h， 生成 (2S)-6''-O-acetylprunin
  参考文献：
  名称：

  Biocatalytic preparation of alkyl esters of citrus flavanone glucoside prunin in organic media

  摘要：

  The biocatalytic preparation of alkyl esters of prunin, a flavanone glucoside derivative of citric flavonoid naringin, was performed in organic media using two commercial immobilized lipases: Novozym 435 (Candida antarctica lipase B immobilized on an acrylic resin) and Lipozyme RM IM (Rhizomucor miehei lipase immobilized on an anion exchange resin). The influence of several reaction parameters on the performance and regioselectivity of the biocatalytic process was investigated using four solvents (acetone, acetonitrile, tetrahydrofurane and t-butanol) and vinyl laurate as a donor. The biocatalytic modification of prunin was strongly dependant on the solvent, the molar ratio of the substrates, the enzyme and the chain length of the donor. The acylation was highly regioselective, obtaining 6 ''-O-acyl monoesters except when the donor was vinyl acetate in which case a diester seemed to be formed. Novozym 435 proved to be a more efficient biocatalyst than Lipozyme RM IM. In acetone and acetonitrile, derivatives with a 100% conversion yield were synthesized after only 6 h of reaction at 50 degrees C. The modified derivatives preserved the antiradical activity of the flavanone glucoside and their solubility notably increased in the hydrophobic medium 1-octanol. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.procbio.2010.07.022

文献信息

• Biocatalytic preparation of alkyl esters of citrus flavanone glucoside prunin in organic media
  作者：Gustavo Céliz、Mirta Daz

  DOI：10.1016/j.procbio.2010.07.022

  日期：2011.1

  The biocatalytic preparation of alkyl esters of prunin, a flavanone glucoside derivative of citric flavonoid naringin, was performed in organic media using two commercial immobilized lipases: Novozym 435 (Candida antarctica lipase B immobilized on an acrylic resin) and Lipozyme RM IM (Rhizomucor miehei lipase immobilized on an anion exchange resin). The influence of several reaction parameters on the performance and regioselectivity of the biocatalytic process was investigated using four solvents (acetone, acetonitrile, tetrahydrofurane and t-butanol) and vinyl laurate as a donor. The biocatalytic modification of prunin was strongly dependant on the solvent, the molar ratio of the substrates, the enzyme and the chain length of the donor. The acylation was highly regioselective, obtaining 6 ''-O-acyl monoesters except when the donor was vinyl acetate in which case a diester seemed to be formed. Novozym 435 proved to be a more efficient biocatalyst than Lipozyme RM IM. In acetone and acetonitrile, derivatives with a 100% conversion yield were synthesized after only 6 h of reaction at 50 degrees C. The modified derivatives preserved the antiradical activity of the flavanone glucoside and their solubility notably increased in the hydrophobic medium 1-octanol. (C) 2010 Elsevier Ltd. All rights reserved.