6'-O-cinnamoyl-arbutin | 221688-07-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6'-O-cinnamoyl-arbutin
• 英文别名: robustasideA；[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-hydroxyphenoxy)oxan-2-yl]methyl 3-phenylprop-2-enoate
• CAS: 221688-07-9
• 化学式: C₂₁H₂₂O₈
• 分子量: 402.401
• InChiKey: HEHKQMPTGIUPMG-QNDFHXLGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  肉桂酸乙烯酯 、 熊果苷 在 immobilized lipase from Penicillium expansum 作用下， 以 四氢呋喃 为溶剂， 反应 68.0h， 以88%的产率得到6'-O-cinnamoyl-arbutin
  参考文献：
  名称：

  Highly regioselective synthesis of novel aromatic esters of arbutin catalyzed by immobilized lipase from Penicillium expansum

  摘要：

  Ester derivatives of phenolic glycosides have attracted more attention in food, cosmetic and pharmaceutical industries, due to their potent biological activities. In the present study, a group of novel aromatic esters of arbutin were successfully synthesized by using immobilized lipase from Penicillium expansum with excellent 6'-regioselectivities (>99%) and moderate to excellent isolated yields (68-93%), except for 6'-O-vanilloyl-arbutin and 6'-O-(p-hydroxycinnamoyl)-arbutin with 28% and 34% yields, respectively. Among all the acyl donors tested, the lipase was most active towards vinyl 3-phenylpropionate, while remarkable decrease in the activity was recorded when the phenyl of acyl donors carried the hydroxyl and/or methoxyl. (C) 2010 Published by Elsevier B.V.

  DOI：

  10.1016/j.molcatb.2010.07.003

文献信息

• Highly regioselective synthesis of novel aromatic esters of arbutin catalyzed by immobilized lipase from Penicillium expansum
  作者：Rong-Ling Yang、Ning Li、Min Ye、Min-Hua Zong

  DOI：10.1016/j.molcatb.2010.07.003

  日期：2010.11

  Ester derivatives of phenolic glycosides have attracted more attention in food, cosmetic and pharmaceutical industries, due to their potent biological activities. In the present study, a group of novel aromatic esters of arbutin were successfully synthesized by using immobilized lipase from Penicillium expansum with excellent 6'-regioselectivities (>99%) and moderate to excellent isolated yields (68-93%), except for 6'-O-vanilloyl-arbutin and 6'-O-(p-hydroxycinnamoyl)-arbutin with 28% and 34% yields, respectively. Among all the acyl donors tested, the lipase was most active towards vinyl 3-phenylpropionate, while remarkable decrease in the activity was recorded when the phenyl of acyl donors carried the hydroxyl and/or methoxyl. (C) 2010 Published by Elsevier B.V.