3-p-coumaroylquinic acid | 32451-86-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-p-coumaroylquinic acid
• 英文别名: 3-O-p-coumaroylquinic acid；5-p-coumaroylquinic acid；p-coumaroylquinic acid；5-O-p-coumaroylquinic acid；3-O-coumaroylquinic acid；(1R,3R,4S,5R)-1,3,4-trihydroxy-5-[3-(4-hydroxyphenyl)prop-2-enoyloxy]cyclohexane-1-carboxylic acid
• CAS: 32451-86-8
• 化学式: C₁₆H₁₈O₈
• 分子量: 338.314
• InChiKey: BMRSEYFENKXDIS-UNIGVISCSA-N

物化性质

• 熔点：
  195-199 °C(Solv: water (7732-18-5))
• 沸点：
  613.2±55.0 °C(Predicted)
• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  145
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  methyl (-)-quinate 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 D(+)-10-樟脑磺酸 、 水 、 原甲酸三甲酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 168.0h， 生成 3-p-coumaroylquinic acid
  参考文献：
  名称：

  Synthesis of p -coumaroylquinic acids and analysis of their interconversion

  摘要：

  The synthesis of four isomers of p-coumaroylquinic acids was performed by esterification of p-acetylcoumaroylchloride with a suitably protected (-)-quinic acid. All isomers have been characterized by means of NMR spectroscopy and circular dichroism. Acyl migration was observed in the synthesis of 3-0-p-coumaroylquinic acid and 4-O-p-coumaroylquinic acid. Calculations on the most stable conformations of all isomers have also been performed to explain the acyl migration observed during the synthesis procedure. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2017.01.015

文献信息

• The biosynthesis of hydroxycinnamoyl quinate esters and their role in the storage of cocaine in Erythroxylum coca
  作者：José Carlos Pardo Torre、Gregor W. Schmidt、Christian Paetz、Michael Reichelt、Bernd Schneider、Jonathan Gershenzon、John C. D’Auria

  DOI：10.1016/j.phytochem.2012.09.009

  日期：2013.7

  Complexation of alkaloids is an important strategy plants utilize to facilitate storage in vacuoles and avoid autotoxicity. Previous studies have implicated hydroxycinnamoyl quinate esters in the complexation of purine alkaloids in Coffea arabica. The goal of this study was to determine if Erythroxylum coca uses similar complexation agents to store abundant tropane alkaloids, such as cocaine and cinnamoyl cocaine. Metabolite analysis of various E. coca organs established a close correlation between levels of coca alkaloids and those of two hydroxycinnamoyl esters of quinic acid, chlorogenic acid and 4-coumaroyl quinate. The BAHD acyltransferase catalyzing the final step in hydroxycinnamoyl quinate biosynthesis was isolated and characterized, and its gene expression found to correlate with tropane alkaloid accumulation. A physical interaction between chlorogenic acid and cocaine was observed and quantified in vitro using UV and NMR spectroscopic methods yielding similar values to those reported for a caffeine chlorogenate complex in C arabica. These results suggest that storage of cocaine and other coca alkaloids in large quantities in E. coca involves hydroxycinnamoyl quinate esters as complexation partners. (C) 2012 Elsevier Ltd. All rights reserved.