3-hydroxy-5-[(2R,3R)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-2-yl]cyclohexa-3,5-diene-1,2-dione | 40479-75-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-hydroxy-5-[(2R,3R)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-2-yl]cyclohexa-3,5-diene-1,2-dione
• CAS: 40479-75-2
• 化学式: C₁₅H₁₂O₇
• 分子量: 304.256
• InChiKey: HALDNBPERDFFRK-IUODEOHRSA-N

物化性质

• 沸点：
  640.0±55.0 °C(predicted)
• 密度：
  1.750±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  124
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  邻苯二胺 、 (-)-表没食子儿茶素 在 碳酸氢钠 、 potassium hexacyanoferrate(III) 、 溶剂黄146 作用下， 以 水 、 甲醇 为溶剂， 反应 1.67h， 生成 、 (2R,3R)-2-[3,4,5-trihydroxy-2-[1-hydroxy-3-[(2R,3R)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-2-yl]phenazin-2-yl]phenyl]-3,4-dihydro-2H-chromene-3,5,7-triol 、 (2R,3R)-2-[3,4,5-trihydroxy-2-[4-hydroxy-2-[(2R,3R)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-2-yl]phenazin-1-yl]phenyl]-3,4-dihydro-2H-chromene-3,5,7-triol 、 3-hydroxy-5-[(2R,3R)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-2-yl]cyclohexa-3,5-diene-1,2-dione
  参考文献：
  名称：

  Enzymatic oxidation of gallocatechin and epigallocatechin: Effects of C-ring configuration on the reaction products

  摘要：

  Tea leaf is rich in pyrogallol-type catechins, and their oxidation is important in the generation of black tea polyphenols. In the present study, the enzymatic oxidation of three pyrogallol-type catechins, (+)- and (-)-gallocatechins and (-)-epigallocatechin, was compared. The reactions yielded unstable quitione products, which were trapped as condensation products with o-phenylenediamine. The oxidation of' (+)-gallocatechin proceeded very slowly compared to the reaction of (-)-epigallocatechiii, and yielded a proepi t hea fl agallin- type dimer as the major product, though oxidation of (-)-epigallocatechin gave predominantly dehydrotheasinensin C. The cis-con figuration of' the C-3 hydroxyl group and the B-ring of (-)-epigallocatechin was apparently crucial for rapid and selective production of dehydrotheasinensin C. Oxidation of (-)-gallocatechin proceeded in a manner similar to that of (+)-gallocatechin, and produced an enantiomer of the (+)-gallocatechin product. The results suggest that enzymes catalyze oxidation of the pyrogallol B-ring to the o-quinone, with subsequent non-enzymatic coupling reactions proceed under highly steric control. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2007.08.007

文献信息

• MANUFACTURING METHOD FOR THEAFLAVINS USING RAW TEA LEAVES
  申请人：Takemoto Masumi

  公开号：US20110059215A1

  公开（公告）日：2011-03-10

  Disclosed is a method for cheaply and easily producing theaflavins. After adding a large quantity of water to raw tea leaves that have not undergone wilt treatment, the tea leaves are crushed in a blender and then let stand, shaken, or agitated, thereby efficiently convening four types of catechins in the raw tea leaves to theaflavins. After adding water and crushing the raw tea leaves, letting the tea leaves stand allows theaflavins to be selectively obtained with high yield. Shaking the raw tea leaves which have had water added and been crushed allows four types of theaflavins to be obtained with high yield. The generated theaflavins can be easily collected using a method such as extraction by organic solvent.

  本发明公开了一种便宜且容易生产茶黄素的方法。将未经凋萎处理的生茶叶加入大量水中，将茶叶在搅拌器中研磨后静置、摇晃或搅拌，从而有效地将生茶叶中的四种儿茶素转化为茶黄素。在加水和研磨生茶叶后，让茶叶静置可高效地选择性地获得茶黄素。将加水和研磨后的生茶叶摇晃可高效地获得四种茶黄素。可使用有机溶剂提取等方法轻松地收集所产生的茶黄素。
• PROCESS FOR SELECTIVE PRODUCTION OF THEAFLAVIN
  申请人：Takemoto Masumi

  公开号：US20100136636A1

  公开（公告）日：2010-06-03

  The present invention provides a method for selective production of theaflavin in large amounts at high yield, and in an easy and inexpensive manner. Specifically, it relates to a method for selective production of theaflavin whereby a processed plant extract containing epicatechin, epigallocatechin, epicatechin-3-O-gallate and epigallocatechin-3-O-gallate is combined with a plant cell culture having peroxidase activity for selective production of theaflavin.

  本发明提供了一种在高产量和易于且低成本的情况下选择性大量生产茶黄素的方法。具体而言，它涉及一种选择性生产茶黄素的方法，其中将含有表儿茶素，表儿茶素3-O-没食子酸酯和表儿茶素-3-O-没食子酸酯的加工植物提取物与具有过氧化物酶活性的植物细胞培养物结合，以选择性地生产茶黄素。
• Enzymatic oxidation of gallocatechin and epigallocatechin: Effects of C-ring configuration on the reaction products
  作者：Yosuke Matsuo、Yuko Yamada、Takashi Tanaka、Isao Kouno

  DOI：10.1016/j.phytochem.2007.08.007

  日期：2008.12

  Tea leaf is rich in pyrogallol-type catechins, and their oxidation is important in the generation of black tea polyphenols. In the present study, the enzymatic oxidation of three pyrogallol-type catechins, (+)- and (-)-gallocatechins and (-)-epigallocatechin, was compared. The reactions yielded unstable quitione products, which were trapped as condensation products with o-phenylenediamine. The oxidation of' (+)-gallocatechin proceeded very slowly compared to the reaction of (-)-epigallocatechiii, and yielded a proepi t hea fl agallin- type dimer as the major product, though oxidation of (-)-epigallocatechin gave predominantly dehydrotheasinensin C. The cis-con figuration of' the C-3 hydroxyl group and the B-ring of (-)-epigallocatechin was apparently crucial for rapid and selective production of dehydrotheasinensin C. Oxidation of (-)-gallocatechin proceeded in a manner similar to that of (+)-gallocatechin, and produced an enantiomer of the (+)-gallocatechin product. The results suggest that enzymes catalyze oxidation of the pyrogallol B-ring to the o-quinone, with subsequent non-enzymatic coupling reactions proceed under highly steric control. (c) 2007 Elsevier Ltd. All rights reserved.