3-O-(cis-caffeoyl)quinic acid | 32719-11-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-(cis-caffeoyl)quinic acid
• 英文别名: cis-3-O-caffeoylquinic acid；cis-5-o-caffeoylquinic acid；cis-5-caffeoylquinic acidc；5-cis-caffeoylquinic acid；cis-3-caffeoylquinic acid；cis-5-caffeoylquinic acid；(Z)-Neochlorogenic acid；(1R,3R,4S,5R)-3-[(Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4,5-trihydroxycyclohexane-1-carboxylic acid
• CAS: 32719-11-2
• 化学式: C₁₆H₁₈O₉
• 分子量: 354.314
• InChiKey: CWVRJTMFETXNAD-DJTMHQFBSA-N

物化性质

• 沸点：
  665.0±55.0 °C(Predicted)
• 密度：
  1.65±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  25
• 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：
  165
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3-O-(cis-caffeoyl)quinic acid 反应 4.0h， 生成 新绿原酸
  参考文献：
  名称：

  Identification and Quantification of Phenolic Compounds from the Forage Legume Sainfoin (Onobrychis viciifolia)

  摘要：

  Phenolic compounds of sainfoin (Onobrychis viciifolia) variety Cotswold Common are assumed to contribute to its nutritive value and bioactive properties. A purified acetone/water extract was separated by Sephadex LH-20 gel chromatography. Sixty-three phenolic and other aromatic compounds were identified by means of chemical, chromatographic, and spectroscopic methods. Reverse phase HPLC with diode array and chemical reaction detection was used to investigate the phenolic composition of different plant organs. All plant parts showed specific phenolic profiles. Moreover, there were considerable variations in the phenolic content among individual plants of the same variety. The three most abundant phenolic compounds were found to be arbutin [predominant in petiols, 17.7 mg/g of dry weight (DW)], rutin (predominant in leaves, 19.9 mg/g of DW), and catechin (predominant flavanol in petiols, 3.5 mg/g of DW). The present study reveals that the phenolic profile of sainfoin is even more complex than hitherto assumed.

  DOI：

  10.1021/jf900625r
• 作为产物：
  描述：

  新绿原酸 以 甲醇 为溶剂， 反应 5.0h， 生成 3-O-(cis-caffeoyl)quinic acid
  参考文献：
  名称：

  由二咖啡酰奎尼酸的顺式几何异构体形成的优选碱金属加合物允许在超高效液相色谱/四极杆飞行时间质谱法中对其反式异构体进行有效区分。

  摘要：

  理性咖啡酰奎尼酸（CQA）衍生物是一组结构多样的植物化学物质，由于它们具有许多健康益处，因此引起了人们的关注。这些分子的结构多样性部分归因于区域和几何异构现象的存在。这种结构多样性妨碍了植物提取物中这些分子的准确注释。质谱（MS）已成功用于区分CQA衍生物的不同区域异构体；然而，事实证明，对这些分子的几何异构体进行准确区分是一项艰巨的任务。方法采用超高效液相色谱/四极杆飞行时间质谱（UHPLC / QTOFMS）方法在负离子化模式下对diCQA的甲醇溶液进行紫外线辐射分析。通过改变毛细管电压和锥孔电压来优化源内碰撞诱导解离（ISCID）方法，以实现MS分析过程中diCQA的UV生成的几何异构体之间的差异碎片化模式。结果毛细管电压的变化并没有引起四种几何异构体的断裂图谱的显着差异，而视锥电压的变化却导致了断裂图谱的显着差异。结果还首次显示，与diCQAs的反式对应物相比，diCQAs的顺式几

  DOI：

  10.1002/rcm.7526

文献信息

• Effect of Weakly Basic Conditions on the Separation and Purification of Flavonoids and Glycosides from Chrysanthemum morifolium Tea
  作者：Yuxiao Wang、Zhenzhen Xu、Yue Wu、Mo Li、Sicheng Pang、Zhe Liang、Yuanying Ni

  DOI：10.3390/molecules24020297

  日期：——

  Tea brewed from chrysanthemum flowers has been widely used in Chinese medicine. The possibly medicinal compounds in Chrysanthemum morifolium tea can be purified by preparative high performance liquid chromatography (HPLC), but this is usually done with acidic conditions, which leads to the hydrolysis of glycosides. In hopes of avoiding this hydrolysis, we explored the effect of weakly basic conditions on the separation and purification of flavonoids and glycosides from Chrysanthemum morifolium. We also explored the effects of weakly basic conditions on chlorogenic acid (3-CQA) and apigenin-7-O-glucoside (A7G). Our results show that the concentration of the weakly basic ammonium hydrogen carbonate and time had no significant effect on A7G, p < 0.01, but it had a significant effect on 3-CQA, p < 0.01. HPLC and ultraviolet (UV) analysis showed that the structure of 3-CQA is destroyed in weakly basic conditions. Caffeic acid, quinic acid, and 3,4-dihydroxymandelic acid, which is a hydrolysate of 3-CQA, were identified by ultra-performance liquid chromatography quadrupole time-of-flight mass spectrometry (UPLC-Q-TOF-MS). The results showed that weakly basic conditions could be used for the purification of flavonoids and glycosides but not for caffeoylquinic acids. Moreover, our work clarified the hydrolysis behaviour of caffeoylquinic acids, which can be helpful for research into their functional aspects.

  菊花茶被广泛应用于中药。菊花茶中可能含有的药用化合物可以通过制备性高效液相色谱（HPLC）进行纯化，但通常在酸性条件下进行，这会导致糖苷的水解。为了避免这种水解，我们探讨了弱碱性条件对从菊花茶中分离和纯化黄酮类化合物和糖苷的影响。我们还探讨了弱碱性条件对绿原酸（3-CQA）和芹菜素-7-O-葡萄糖苷（A7G）的影响。我们的结果显示，弱碱性氢碳酸铵的浓度和时间对A7G没有显著影响，p <0.01，但对3-CQA有显著影响，p <0.01。HPLC和紫外（UV）分析显示，在弱碱性条件下，3-CQA的结构被破坏。通过超高效液相色谱四极杆飞行时间质谱（UPLC-Q-TOF-MS）鉴定了咖啡酸、奎宁酸和3,4-二羟基苯乙酸，这是3-CQA的水解产物。结果表明，弱碱性条件可用于黄酮类化合物和糖苷的纯化，但不适用于烟酰奎宁酸。此外，我们的研究阐明了烟酰奎宁酸的水解行为，这对研究其功能方面可能有所帮助。
• Thermal Stability of 5-<i>o</i>-Caffeoylquinic Acid in Aqueous Solutions at Different Heating Conditions
  作者：Andrzej L. Dawidowicz、Rafal Typek

  DOI：10.1021/jf103373t

  日期：2010.12.22

  Chlorogenic acid is a naturally occurring phenolic compound found in all higher plants. This component, being the ester of caffeic acid with quinic acid, is an important biosynthetic intermediate and plays an important role in the plant’s response to stress. Potential uses of chlorogenic acid are suggested in pharmaceuticals, foodstuffs, feed additives, and cosmetics due to its recently discovered

  绿原酸是在所有高等植物中发现的天然酚类化合物。该成分是咖啡酸与奎尼酸的酯，是重要的生物合成中间体，在植物对逆境的反应中起重要作用。由于其最近发现的生物医学活性，建议在药物，食品，饲料添加剂和化妆品中潜在使用绿原酸。这一发现引起了对绿原酸性质，其异构体及其天然存在的新兴趣。已经发现，在加热水溶液时，由5-邻-咖啡酰奎宁酸可以形成多达九种化合物（绿原酸衍生物及其与水的反应产物）。其中三个，两个羟基化了5- o-咖啡酰奎尼酸衍生物和4，5-二咖啡酰奎尼酸尚未被报道。每种形成的组分的量取决于加热时间和温度。提出的结果对研究植物新陈代谢并寻找新的植物成分的研究人员很重要。转化产物可能被错误地视为新成分，而在检查过的植物中以前找不到，或者可能是错误估计植物成分的原因。
• Identification and Quantification of Phenolic Compounds from the Forage Legume Sainfoin (Onobrychis viciifolia)
  作者：Ionela Regos、Andrea Urbanella、Dieter Treutter

  DOI：10.1021/jf900625r

  日期：2009.7.8

  Phenolic compounds of sainfoin (Onobrychis viciifolia) variety Cotswold Common are assumed to contribute to its nutritive value and bioactive properties. A purified acetone/water extract was separated by Sephadex LH-20 gel chromatography. Sixty-three phenolic and other aromatic compounds were identified by means of chemical, chromatographic, and spectroscopic methods. Reverse phase HPLC with diode array and chemical reaction detection was used to investigate the phenolic composition of different plant organs. All plant parts showed specific phenolic profiles. Moreover, there were considerable variations in the phenolic content among individual plants of the same variety. The three most abundant phenolic compounds were found to be arbutin [predominant in petiols, 17.7 mg/g of dry weight (DW)], rutin (predominant in leaves, 19.9 mg/g of DW), and catechin (predominant flavanol in petiols, 3.5 mg/g of DW). The present study reveals that the phenolic profile of sainfoin is even more complex than hitherto assumed.
• Preferential alkali metal adduct formation by <i>cis</i> geometrical isomers of dicaffeoylquinic acids allows for efficient discrimination from their <i>trans</i> isomers during ultra-high-performance liquid chromatography/quadrupole time-of-flight mass spectrometry
  作者：Mpho M. Makola、Paul. A Steenkamp、Ian A. Dubery、Mwadham M. Kabanda、Ntakadzeni E. Madala

  DOI：10.1002/rcm.7526

  日期：2016.4.30

  RATIONALE Caffeoylquinic acid (CQA) derivatives are a group of structurally diverse phytochemicals that have attracted attention due to their many health benefits. The structural diversity of these molecules is due in part to the presence of regio- and geometrical isomerism. This structural diversity hampers the accurate annotation of these molecules in plant extracts. Mass spectrometry (MS) is successfully

  理性咖啡酰奎尼酸（CQA）衍生物是一组结构多样的植物化学物质，由于它们具有许多健康益处，因此引起了人们的关注。这些分子的结构多样性部分归因于区域和几何异构现象的存在。这种结构多样性妨碍了植物提取物中这些分子的准确注释。质谱（MS）已成功用于区分CQA衍生物的不同区域异构体；然而，事实证明，对这些分子的几何异构体进行准确区分是一项艰巨的任务。方法采用超高效液相色谱/四极杆飞行时间质谱（UHPLC / QTOFMS）方法在负离子化模式下对diCQA的甲醇溶液进行紫外线辐射分析。通过改变毛细管电压和锥孔电压来优化源内碰撞诱导解离（ISCID）方法，以实现MS分析过程中diCQA的UV生成的几何异构体之间的差异碎片化模式。结果毛细管电压的变化并没有引起四种几何异构体的断裂图谱的显着差异，而视锥电压的变化却导致了断裂图谱的显着差异。结果还首次显示，与diCQAs的反式对应物相比，diCQAs的顺式几