(-)-catechin-6-C-β-D,8-C-β-D-diglucopyranoside

• 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: (-)-catechin-6-C-β-D,8-C-β-D-diglucopyranoside
• 英文别名: (-)-catechin-6-C,8-C-β-D-diglucopyranoside；(2S,3R)-2-(3,4-dihydroxyphenyl)-6,8-bis[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,4-dihydro-2H-chromene-3,5,7-triol
• 化学式: C₂₇H₃₄O₁₆
• 分子量: 614.557
• InChiKey: SPRRLZMLCKUCLC-WAIRMWBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.5
• 重原子数：
  43
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  291
• 氢给体数：
  13
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  葡萄糖 、 (-)-儿茶素 在 potassium carbonate 作用下， 反应 0.17h， 生成 (-)-catechin-8-C-β-D-glucopyranoside 、 (-)-catechin-6-C-β-D-glucopyranoside 、 (-)-catechin-6-C-β-D,8-C-β-D-diglucopyranoside
  参考文献：
  名称：

  Application of a Molecular Sensory Science Approach to Alkalized Cocoa (Theobroma cacao):  Structure Determination and Sensory Activity of Nonenzymatically C-Glycosylated Flavan-3-ols

  摘要：

  Application of comparative taste dilution analyses on nonalkalized and alkalized cocoa powder revealed the detection of a velvety, smoothly astringent tasting fraction, which was predominantly present in the alkalized sample. LC-MS/MS analysis, 1D- and 2D-NMR, and CD spectroscopy as well as model alkalization reactions led to the unequivocal identification of the velvety, smoothly astringent molecules as a series of catechin- and epicatechin-C-glycopyranosides. Besides the previously reported (-)-epicatechin-8-C-beta-D-galactopyranoside, additional flavan-3-ol-C-glycosides, namely, (-)-epicatechin-8- C-beta-D-glucopyranoside, (-)-catechin-8-C-beta-D-glucopyranoside, (-)-catechin-6-C-beta-D-glucopyranoside, (-)-epicatechin-6-C-beta-D-glucopyranoside, (-)-catechin-8-C-beta-D-galactopyranoside, (-)-catechin-6- C-beta-D-galactopyranoside, (-)-catechin-6-C, 8-C-beta-D-diglucopyranoside, (-)-epicatechin-6-C, 8-C-beta-D- digalactopyranoside, (-)-catechin-6-beta-C-D-digalactopyranoside, and epicatechin-6-C, 8-C-beta-Ddiglucopyranoside, were identified for the first time in cocoa. Most surprisingly, these phenol glycoconjugates were demonstrated by model experiments to be formed via a novel nonenzymatic C-glycosylation of flavan-3-ols. Using the recently developed half-tongue test, human recognition thresholds for the astringent and mouth-drying oral sensation were determined to be between 1.1 and 99.5 mu mol/L (water) depending on the sugar and the intramolecular binding position as well as the aglycone.

  DOI：

  10.1021/jf062403+

文献信息

• Application of a Molecular Sensory Science Approach to Alkalized Cocoa (<i>Theobroma cacao</i>):  Structure Determination and Sensory Activity of Nonenzymatically C-Glycosylated Flavan-3-ols
  作者：Timo Stark、Thomas Hofmann

  DOI：10.1021/jf062403+

  日期：2006.12.1

  Application of comparative taste dilution analyses on nonalkalized and alkalized cocoa powder revealed the detection of a velvety, smoothly astringent tasting fraction, which was predominantly present in the alkalized sample. LC-MS/MS analysis, 1D- and 2D-NMR, and CD spectroscopy as well as model alkalization reactions led to the unequivocal identification of the velvety, smoothly astringent molecules as a series of catechin- and epicatechin-C-glycopyranosides. Besides the previously reported (-)-epicatechin-8-C-beta-D-galactopyranoside, additional flavan-3-ol-C-glycosides, namely, (-)-epicatechin-8- C-beta-D-glucopyranoside, (-)-catechin-8-C-beta-D-glucopyranoside, (-)-catechin-6-C-beta-D-glucopyranoside, (-)-epicatechin-6-C-beta-D-glucopyranoside, (-)-catechin-8-C-beta-D-galactopyranoside, (-)-catechin-6- C-beta-D-galactopyranoside, (-)-catechin-6-C, 8-C-beta-D-diglucopyranoside, (-)-epicatechin-6-C, 8-C-beta-D- digalactopyranoside, (-)-catechin-6-beta-C-D-digalactopyranoside, and epicatechin-6-C, 8-C-beta-Ddiglucopyranoside, were identified for the first time in cocoa. Most surprisingly, these phenol glycoconjugates were demonstrated by model experiments to be formed via a novel nonenzymatic C-glycosylation of flavan-3-ols. Using the recently developed half-tongue test, human recognition thresholds for the astringent and mouth-drying oral sensation were determined to be between 1.1 and 99.5 mu mol/L (water) depending on the sugar and the intramolecular binding position as well as the aglycone.