pro-oolongtheanin-3'-O-gallate | 1485592-98-0

• 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: pro-oolongtheanin-3'-O-gallate
• 英文别名: [(2R,3R)-2-[(3aS,9bS)-9-[(2R,3R)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyl)oxy-3,4-dihydro-2H-chromen-2-yl]-3a,6,7-trihydroxy-3,4-dioxo-9bH-cyclopenta[c]chromen-1-yl]-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
• CAS: 1485592-98-0
• 化学式: C₄₄H₃₂O₂₂
• 分子量: 912.725
• InChiKey: GMNUHYFRRUWLKD-IFTCQGBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.53
• 重原子数：
  66.0
• 可旋转键数：
  6.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  377.42
• 氢给体数：
  13.0
• 氢受体数：
  22.0

反应信息

• 作为反应物：
  描述：

  pro-oolongtheanin-3'-O-gallate 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.33h， 以11.4 mg的产率得到
  参考文献：
  名称：

  Isolation of key intermediates during formation of oolongtheanins

  摘要：

  Oolongtheanin-3'-O-gallate (2b) was obtained by treatment of (-)-EGCg (1d) with CuCl2. This transformation was achieved over three steps, with the isolation of two intermediates; their chemical structures were determined through derivatization reactions, MS, and 1D/2D NMR techniques. One intermediate was identified as dehydrotheasinensin A (3); the other was identified as the novel dimer pro-oolongtheanin-3'-O-gallate (6). Compound 3 was converted to 6 by heating in aprotic solvent, and compound 6 was converted to 2b by addition of water. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.10.069
• 作为产物：
  描述：

  (-)-表没食子儿茶素没食子酸酯 在 copper(II) choride dihydrate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 8.0h， 生成 pro-oolongtheanin-3'-O-gallate
  参考文献：
  名称：

  Isolation of key intermediates during formation of oolongtheanins

  摘要：

  Oolongtheanin-3'-O-gallate (2b) was obtained by treatment of (-)-EGCg (1d) with CuCl2. This transformation was achieved over three steps, with the isolation of two intermediates; their chemical structures were determined through derivatization reactions, MS, and 1D/2D NMR techniques. One intermediate was identified as dehydrotheasinensin A (3); the other was identified as the novel dimer pro-oolongtheanin-3'-O-gallate (6). Compound 3 was converted to 6 by heating in aprotic solvent, and compound 6 was converted to 2b by addition of water. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.10.069

文献信息

• Synthesis of oolongtheanins and their inhibitory activity on micellar cholesterol solubility in vitro
  作者：Kazuki Ogawa、Sayumi Hirose、Hitomi Yamamoto、Masaya Shimada、Satoshi Nagaoka、Emiko Yanase

  DOI：10.1016/j.bmcl.2015.01.002

  日期：2015.2

  The synthesis of oolongtheanins (1a-d) was accomplished from EGC and/or EGCg in three steps. Oolongtheanin-3'-O-gallate (1b) showed more potent inhibitory activity on micellar cholesterol solubility than did EGCg. (C) 2015 Elsevier Ltd. All rights reserved.