3,7-O-diacetyl-(-)-epicatechin

• 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: 3,7-O-diacetyl-(-)-epicatechin
• 英文别名: 3,7-diacetyl (-) epicatechin；3,7-diacetoxy epicatechin；[(2R,3R)-7-acetyloxy-2-(3,4-dihydroxyphenyl)-5-hydroxy-3,4-dihydro-2H-chromen-3-yl] acetate
• 化学式: C₁₉H₁₈O₈
• 分子量: 374.347
• InChiKey: GUXBTJCMYDMXRO-RTBURBONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (-)-epicatechin pentaacetate 在 porcine liver esterase 作用下， 以 丙酮 为溶剂， 反应 9.0h， 生成 3,7-O-diacetyl-(-)-epicatechin 、 3,7,4'-triacetoxy epicatechin 、 3,7,3'-triacetoxy epicatechin 、 3,7,3',4'-tetraacetyl (-)-epicatechin
  参考文献：
  名称：

  Studies on the porcine liver esterase-catalyzed hydrolysis of pentaacetyl catechin and epicatechin: Application to the synthesis of novel dimers and trimers

  摘要：

  Porcine liver esterase-catalyzed hydrolysis of 3,5,7,30,40-pentaacetylated catechin was studied. The selectivity of the enzyme in hydrolyzing the acetate moiety is time dependent. Careful control of the duration of hydrolysis makes it possible to isolate the differentially protected catechins. Similar result was also obtained in the epicatechin series. These results are important for elaboration of epicatechin or catechin into different derivatives with defined regiochemistry. These include novel dimeric and trimeric architectures. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.07.058

文献信息

• Studies on the porcine liver esterase-catalyzed hydrolysis of pentaacetyl catechin and epicatechin: Application to the synthesis of novel dimers and trimers
  作者：Amit Basak、Sanket Das、Shrabani Bisai

  DOI：10.1016/j.bmcl.2008.07.058

  日期：2008.9

  Porcine liver esterase-catalyzed hydrolysis of 3,5,7,30,40-pentaacetylated catechin was studied. The selectivity of the enzyme in hydrolyzing the acetate moiety is time dependent. Careful control of the duration of hydrolysis makes it possible to isolate the differentially protected catechins. Similar result was also obtained in the epicatechin series. These results are important for elaboration of epicatechin or catechin into different derivatives with defined regiochemistry. These include novel dimeric and trimeric architectures. (C) 2008 Elsevier Ltd. All rights reserved.