4-O-caffeoylquinic acid

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-O-caffeoylquinic acid
• 英文别名: 4-O-caffaeoylquinic acid；4-O-caffeoyl quinic acid；1-O-caffeoylquinic acid；crypto-chlorogenic acid；4-O-caffeoylquinicacid；4-O-caffeoylqunic acid
• 化学式: C₁₆H₁₈O₉
• 分子量: 354.314
• InChiKey: GYFFKZTYYAFCTR-NCZKRNLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.65
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  164.75
• 氢给体数：
  6.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  4-O-caffeoylquinic acid 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：

  绿原酸 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 6.0h， 以34.5%的产率得到4-O-caffeoylquinic acid
  参考文献：
  名称：

  一种隐绿原酸的制备方法

  摘要：

  本发明公开了一种隐绿原酸的制备方法，该制备方法步骤为：取绿原酸，甲醇溶解，然后加1～2mol/L盐酸，搅拌反应6～8h，1～2mol/LNaOH溶液调pH至中性，浓缩，甲醇溶解，过滤，减压浓缩，加水溶解，滤过，得滤液；取滤液经反相C18柱预处理，水洗，收集水洗液浓缩，离心，过滤，利用反相工业制备色谱法制备得到隐绿原酸。本发明提供的隐绿原酸的制备方法，经过系统实验筛选得到最佳的酸转化条件和碱中和反应条件，并经过反相工业制备色谱制备得到高纯度的隐绿原酸，产率高，适合大规模制备，取得了很好的技术效果。

  公开号：

  CN105481689B

文献信息

• How to distinguish between cinnamoylshikimate esters and chlorogenic acid lactones by liquid chromatography-tandem mass spectrometry
  作者：Rakesh Jaiswal、Marius Febi Matei、Frank Ullrich、Nikolai Kuhnert

  DOI：10.1002/jms.1972

  日期：2011.9

  In this study, liquid chromatography–tandem mass spectrometry (LC–MSn; n = 2–3) has been used to characterize and distinguish chlorogenic acid lactones from cinnamoylshikimate esters. This is the first time when an LC–MSn method has been developed to distinguish between these two isomeric classes of compounds formed in particular in food processing from chlorogenic acids at elevated temperature through

  在这项研究中，液相色谱-串联质谱法（LC-MS n；n  = 2-3）已用于表征和区分肉桂酰shi草酸酯中的绿原酸内酯。这是首次开发出LC-MS n方法来区分这两种异构体类型的化合物，特别是在食品加工中，由于高温会因水分损失而从绿原酸中形成的这两种化合物。液相异构绿原酸内酯和sh草酸酯的结构已根据LC-MS n确定碎裂，相对疏水性和碎裂的模式类似于含有二酰基绿原酸内酯和sh草酸酯的二甲氧基肉桂酸，阿魏酸和咖啡酸的合成标准。版权所有©2011 John Wiley＆Sons，Ltd.
• 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
• Polyphenols Are Intensively Metabolized in the Human Gastrointestinal Tract after Apple Juice Consumption
  作者：Kathrin Kahle、Wolfgang Huemmer、Michael Kempf、Wolfgang Scheppach、Thomas Erk、Elke Richling

  DOI：10.1021/jf071942r

  日期：2007.12.1

  Polyphenols are secondary plant compounds showing anticarcinogenic effects both in vitro and in animal experiments and may thus reduce the risk of colorectal cancer in man. The identification of polyphenol metabolites formed via their passage through the small intestine of healthy ileostomy subjects after apple juice consumption is presented. Identification and quantification of polyphenols and their metabolites were performed using HPLC-DAD as well as HPLC-ESI-MS/MS. Total procyanidin content (TPA) was measured, and additionally the mean degree of polymerization (DPm) of the procyanidins was determined in the apple juice and ileostomy effluents. As products of polyphenol metabolism, D-(-)-quinic acid and methyl esters of caffeic acid and p-coumaric acid are liberated from the corresponding hydroxycinnamic acid esters. 1-Caffeoylquinic acid and 3-caffeoylquinic acid were determined as products of isomerization. Phloretin 2'-O-glucoside (phloridzin) and phloretin 2'-O-xyloglucoside were metabolized into the corresponding aglycons phloretin and phloretin 2'-O-glucuronide and all were found in the ileostomy effluent. Ninety percent of the consumed procyanidins were recovered in the ileostomy effluent and therefore would reach the colon under physiologic circumstances. The DPm was reduced (DPm of apple juice = 5.7) and varied depending on the time point of excretion. The gastrointestinal passage seems to play an important role in the colonic availability of apple polyphenols.
• Synthesis of 3-cyclohexylpropyl caffeate from 5-caffeoylquinic acid with consecutive enzymatic conversions in ionic liquid
  作者：Atsushi Kurata、Shintaro Takemoto、Tokio Fujita、Kazuya Iwai、Mina Furusawa、Noriaki Kishimoto

  DOI：10.1016/j.molcatb.2011.01.012

  日期：2011.5

  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.
• 一种隐绿原酸的制备方法
  申请人：江苏康缘药业股份有限公司

  公开号：CN105481689B

  公开（公告）日：2018-04-24

  本发明公开了一种隐绿原酸的制备方法，该制备方法步骤为：取绿原酸，甲醇溶解，然后加1～2mol/L盐酸，搅拌反应6～8h，1～2mol/LNaOH溶液调pH至中性，浓缩，甲醇溶解，过滤，减压浓缩，加水溶解，滤过，得滤液；取滤液经反相C18柱预处理，水洗，收集水洗液浓缩，离心，过滤，利用反相工业制备色谱法制备得到隐绿原酸。本发明提供的隐绿原酸的制备方法，经过系统实验筛选得到最佳的酸转化条件和碱中和反应条件，并经过反相工业制备色谱制备得到高纯度的隐绿原酸，产率高，适合大规模制备，取得了很好的技术效果。