异绿原酸A | 2450-53-5

• 物质功能分类: 生物化工 - 提取物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 异绿原酸A
• 中文别名: 3,5-二咖啡酰奎宁酸；异绿原酸 A
• 英文名称: Isochlorogenic acid A
• 英文别名: (3R,5R)-3,5-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,4-dihydroxycyclohexane-1-carboxylic acid；3,5-di-O-caffeoylquinic acid；(1s,3R,4s,5R)-3,5-O-dicaffeoylquinic acid；3,5-di-O-caffeoyl-epi-quinic acid；3,5‐dicaffeoylquinic acid；3,5-di-O-caffeoyl-L-quinic acid；(-) 3,5-dicaffeoylquinic acid；3,5-di-O-caffeoyl-quinic acid
• CAS: 2450-53-5；16758-05-7；89919-61-9；89919-62-0；101222-97-3
• 化学式: C₂₅H₂₄O₁₂
• 分子量: 516.458
• InChiKey: KRZBCHWVBQOTNZ-BBLPPJRLSA-N

物化性质

• 熔点：
  >175°C (dec.)
• 沸点：
  826.2±65.0 °C(Predicted)
• 密度：
  1?+-.0.1 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1.03
• 重原子数：
  37.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  211.28
• 氢给体数：
  7.0
• 氢受体数：
  11.0

安全信息

• WGK Germany：
  3

制备方法与用途

生物活性

Isochlorogenic acid A (3,5-Dicaffeoylquinic acid) 是一种具有抗氧化和抗炎活性的天然酚酸。

靶点

Human Endogenous Metabolite

化学性质 

类白色结晶粉末，可溶于甲醇、乙醇、DMSO等有机溶剂，来源于金银花，忍冬，杜仲、菊花。

用途 

异绿原酸A具有抗血小板聚集、抗菌、消炎的作用。

用途 

用于含量测定/鉴定/药理实验等。
药理药效:清热解毒，抗菌消炎。

反应信息

• 作为反应物：
  描述：

  异绿原酸A 在 Candida antarctica lipase B 作用下， 40.0~80.0 ℃ 、101.33 kPa 条件下， 反应 28.0h， 生成 3-cyclohexylpropyl caffeate
  参考文献：
  名称：

  Synthesis of 3-cyclohexylpropyl caffeate from 5-caffeoylquinic acid with consecutive enzymatic conversions in ionic liquid

  摘要：

  We developed a convenient one-pot procedure for conversion of 5-caffeoylquinic acid to 3-cyclohexylpropyl caffeate, which exhibits an antiproliferative effect toward various human tumor cells. The procedure was comprised of two consecutive reactions by chlorogenate hydrolase (EC 3.1.1.42) from Aspergillus japonicus and Candida antarctica lipase B, and was performed using an ionic liquid, 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide, as the reaction solvent. When various caffeoylquinic acids from coffee beans, namely, 3-caffeoylquinic acid, 4-caffeoylquinic acid, 5-caffeoylquinic acid,3,5-dicaffeoylquinic acid, and 4,5-dicaffeoylquinic acid were used, the first alcoholysis reaction with methanol using chlorogenate hydrolase produced methyl caffeate with conversion yields of 60.0%, 61.3%, 86.0%, 92.7%, and 114.0%, respectively, to each individual substrate. Two caffeoyl groups of dicaffeoylquinic acids would be used for the synthesis of methyl caffeate. In the subsequent transesterification reaction by C. antarctica lipase B with 3-cyclohexyl-1-propanol, the methyl caffeate produced was converted to 3-cyclohexylpropyl caffeate under reduced pressure to remove the by-product methanol. In the one-pot synthesis, the methyl caffeate was transesterified efficiently to 3-cyclohexylpropyl caffeate by C. antarctica lipase B with deactivation of chlorogenate hydrolase by taking advantage of the difference between the optimum temperatures for the two enzymes. This system provided 12.8 mM 3-cyclohexylpropyl caffeate from 15 mM 5-caffeoylquinic acid with conversion yield of 85.3%. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2011.01.012
• 作为产物：
  描述：

  1,5-quinide 在 哌啶 、 咪唑 、 4-二甲氨基吡啶 、 pyridine hydrofluoride 、 10% Pd(OH)₂ on C 、 水 、 氢气 、 sodium hydride 、 caesium carbonate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 反应 272.25h， 生成 异绿原酸A
  参考文献：
  名称：

  Total synthesis of 3,5-O-dicaffeoylquinic acid and its derivatives

  摘要：

  We report the first total synthesis of 3,5-O-dicaffeoylquinic acid and its derivatives, 3,5-O-diferuloylquinic acid and 3,5-(3,4-dimethoxycinnamyl)quinic acid, in a nine-step sequence. The key step involves Knoevenagel condensations between vanillin. 3,4-dimethoxybenzaldehyde or 4-hydroxy-3-methoxy-benzaldehyde and the dimalonate ester of quinic acid. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.10.127

文献信息

• How to identify and discriminate between the methyl quinates of chlorogenic acids by liquid chromatography-tandem mass spectrometry
  作者：Rakesh Jaiswal、Nikolai Kuhnert

  DOI：10.1002/jms.1889

  日期：2011.3

  The methyl esters of chlorogenic acids, methyl quinates, are widely distributed in plant materials and frequently appear as extraction artifacts in plant samples. This is the first time when liquid chromatography–tandem mass spectrometry methods have been used for the identification and characterization of the methyl quinates. For this purpose, methyl quinates of mono caffeoylquinic acids and mono feruloylquinic

  绿原酸的甲酯，奎宁酸甲酯，广泛分布在植物材料中，经常作为提取物出现在植物样品中。这是液相色谱串联质谱法首次用于奎宁酸甲酯的鉴定和表征。为此目的，合成了单咖啡酰奎尼酸和单阿魏酰奎尼酸的奎宁甲酯作为真实的标准品。单和二酰基绿原酸的甲基奎宁酸酯在其串联质谱中显示出特征性的断裂模式。二酰基绿原酸的甲基奎宁酸的MS n +1光谱与单酰基衍生物的MS n光谱相同。这些奎宁酸酯在以下位置不产生任何奎宁甲酯峰m / z 205（与负离子模式下m / z 191处的奎宁酸峰相比）。在这些奎宁酸盐的MS n光谱中，肉桂酸部分或肉桂酰基部分被检测为负离子模式的基础峰。与针对绿原酸开发的LC-MS n方法相比，保留时间，洗脱顺序和碎片模式完全不同。这些LC-MS Ñ方法已经被应用于在马黛茶和半圆绿原酸类的甲基奎尼的鉴定和表征的区域异构体（猪殃玉竹）。两种咖啡因酰基奎宁酸甲酯（2和4）被鉴定为3-咖啡因酰基奎宁酸甲