(E)-1-(3,4-dihydroxyphenyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-(2,4,6-trihydroxyphenyl)prop-2-en-1-one | 1011707-83-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-1-(3,4-dihydroxyphenyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-(2,4,6-trihydroxyphenyl)prop-2-en-1-one
• CAS: 1011707-83-7
• 化学式: C₂₁H₂₂O₁₂
• 分子量: 466.398
• InChiKey: KJLRCVMGMDRMCX-ZCTYLCMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  218
• 氢给体数：
  9
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (E)-1-(3,4-dihydroxyphenyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-(2,4,6-trihydroxyphenyl)prop-2-en-1-one 在 咖啡因 作用下， 生成 (Z)-1-(3,4-dihydroxyphenyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-(2,4,6-trihydroxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Thermodynamics and Kinetics of Cyanidin 3-Glucoside and Caffeine Copigments

  摘要：

  The multiequilibrium system of reactions of cyanidin 3-glucoside at acidic and mildly acidic pH was studied in the presence of caffeine as a copigment. The thermodynamic and kinetic constants were determined using the so-called direct and reverse pH jump experiments that were followed by conventional UV-vis spectroscopy or stopped flow coupled to a UV-vis detector, depending on the rate of the monitored process. Compared with that of free anthocyanin, the copigmentation with caffeine extends the domain of the flavylium cation up to less acidic pH values, while in a moderately acidic medium, the quinoidal base becomes more stabilized. As a consequence, the hydration to give the colorless hemiketal is difficult over the entire range of pH values. At pH 1, two adducts were found for the flavylium cation-caffeine interaction, with stoichiometries of 1:1 and 1:2 and association constants of 161 M-1 (K-1) and 21 M-1 (K-2), respectively.

  DOI：

  10.1021/jf4006643
• 作为产物：
  描述：

  (Z)-1-(3,4-dihydroxyphenyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-(2,4,6-trihydroxyphenyl)prop-2-en-1-one 在 咖啡因 作用下， 生成 (E)-1-(3,4-dihydroxyphenyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-(2,4,6-trihydroxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Thermodynamics and Kinetics of Cyanidin 3-Glucoside and Caffeine Copigments

  摘要：

  The multiequilibrium system of reactions of cyanidin 3-glucoside at acidic and mildly acidic pH was studied in the presence of caffeine as a copigment. The thermodynamic and kinetic constants were determined using the so-called direct and reverse pH jump experiments that were followed by conventional UV-vis spectroscopy or stopped flow coupled to a UV-vis detector, depending on the rate of the monitored process. Compared with that of free anthocyanin, the copigmentation with caffeine extends the domain of the flavylium cation up to less acidic pH values, while in a moderately acidic medium, the quinoidal base becomes more stabilized. As a consequence, the hydration to give the colorless hemiketal is difficult over the entire range of pH values. At pH 1, two adducts were found for the flavylium cation-caffeine interaction, with stoichiometries of 1:1 and 1:2 and association constants of 161 M-1 (K-1) and 21 M-1 (K-2), respectively.

  DOI：

  10.1021/jf4006643