1,3,4-tricaeoylquinic acid | 1073897-77-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3,4-tricaeoylquinic acid
• 英文别名: 1,3,4-tricaffeoylquinic acid；1,3,4-TriCQA；(1S,3R,4R,5R)-1,3,4-tris[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-5-hydroxycyclohexane-1-carboxylic acid
• CAS: 1073897-77-4
• 化学式: C₃₄H₃₀O₁₅
• 分子量: 678.603
• InChiKey: ZDYRXGIWSQSHSO-UPHZGLEOSA-N

物化性质

• 沸点：
  947.3±65.0 °C(Predicted)
• 密度：
  1?+-.0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  49
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  258
• 氢给体数：
  8
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  右旋奎宁酸 、 3,4-diacetoxycinnamoyl chloride 在 4-二甲氨基吡啶 、 三乙胺 、 盐酸 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 9.0h， 生成 (-)-1,3,5-tri-O-caffeoylquinic acid 、 1,4,5-O-tricaffeoylquinic acid 、 1,3,4-tricaeoylquinic acid 、 3,4,5-tri-O-caffeoyl-quinic acid
  参考文献：
  名称：

  Characterization and Quantification of Hydroxycinnamate Derivatives in Stevia rebaudiana Leaves by LC-MSⁿ

  摘要：

  Stevia rebaudiana leaves are used as a zero-calorie natural sweetener in a variety of food products in Asian countries, especially in Japan. In this study, the hydroxycinnamate derivatives of S. rebaudiana have been investigated qualitatively and quantitatively by LC-MSn. Twenty-four hydroxycinnainic acid derivatives of quinic and shikimic acid were detected, and 19 of them were successfully characterized to regioisomeric levels; 23 are reported for the first time from this source. These comprise three monocaffeoylquinic acids (M-r 354), seven dicaffeoylquinic acids (M-r 516), one p-coumaroylquinic acid (M-r 338), one feruloylquinic acid (M-r 368), two caffeoyl-feruloylquinic acids (M-r 530), three caffeoylshildmic acids (M-r 336), and two tricaffeoylquinic acids (M-r 678). Cis isomers of di- and tricaffeoylquinic acids were observed as well. Three tricaffeoylquinic acids identified in stevia leaves are reported for the first time in nature. These phenolic compounds identified in stevia might affect the organoleptic properties and add additional beneficial health effects to stevia-based products.

  DOI：

  10.1021/jf202185m