theacitrinin A | 1292312-08-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: theacitrinin A
• CAS: 1292312-08-3
• 化学式: C₂₈H₂₀O₁₄
• 分子量: 580.458
• InChiKey: LYKSEILTGFHDTH-SXHZWGFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.08
• 重原子数：
  42.0
• 可旋转键数：
  3.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  251.74
• 氢给体数：
  9.0
• 氢受体数：
  14.0

反应信息

• 作为产物：
  描述：

  theacitrin C 在 水 、 三氟乙酸 作用下， 反应 1.0h， 以68%的产率得到theacitrinin A
  参考文献：
  名称：

  Production and degradation mechanism of theacitrin C, a black tea pigment derived from epigallocatechin-3-O-gallate via a bicyclo[3.2.1]octane-type intermediate

  摘要：

  Black tea is rich in polyphenols and has been shown to have various health benefits: however, its components have not yet been clarified in detail. Enzymatic oxidation of epigallocatechin-3-O-gallate, the most abundant polyphenol in tea, is thought to contribute significantly to the production of black tea polyphenols. We identified theacitrin C, an unstable black tea pigment, as an enzymatic oxidation product of epigallocatechin-3-O-gallate. Degradation of theacitrin C afforded theacitrinin A and 2,3,5,7-tetrahydroxychroman-3-O-gallate. Furthermore, theacitrinin B, which was isolated from black tea, is deduced to be a degradation product of theacitrin A, the desgalloyl analogue of theacitrin C. The structures of theacitrinins A and B were elucidated based on spectroscopic data. This is the first time that a degradation product of theacitrin has been isolated from black tea. We also examined the influence of esterification of the epigallocatechin C-3 hydroxyl group on the decomposition of bicyclo[3.2.1]octane-type intermediates. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.058