5-O-caffeoyl-shikimic acid | 73263-62-4

• 物质功能分类: 分析化学 - 对照品
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 5-O-caffeoyl-shikimic acid
• 英文别名: 5-O-Caffeoylshikimic acid；5-caffeoylshikimic acid；dactylifric acid；NP-000588；1-Cyclohexene-1-carboxylic acid,5-((3-(3,4-dihydroxyphenyl)-1-oxo-2-p ropenyl)oxy)-3,4-dihydroxy-,(3r-(3alpha,4alpha,5beta))-；(3R,4R,5R)-5-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-3,4-dihydroxycyclohexene-1-carboxylic acid
• CAS: 73263-62-4
• 化学式: C₁₆H₁₆O₈
• 分子量: 336.298
• InChiKey: QMPHZIPNNJOWQI-UMVBOHGHSA-N

物化性质

• 沸点：
  635.1±55.0 °C(Predicted)
• 密度：
  1.60±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  145
• 氢给体数：
  5
• 氢受体数：
  8

制备方法与用途

5-O-咖啡酰莽草酸是一种酸类衍生物，可用作对照品。

反应信息

• 作为产物：
  描述：

  methyl shikimate 在 吡啶 、 4-二甲氨基吡啶 、 水 、 对甲苯磺酸 、 三氟乙酸 、 potassium hydroxide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 17.0h， 生成 5-O-caffeoyl-shikimic acid
  参考文献：
  名称：

  Profiling and Characterization by LC-MSⁿ of the Chlorogenic Acids and Hydroxycinnamoylshikimate Esters in Maté (Ilex paraguariensis)

  摘要：

  The chlorogenic acids of mate (Ilex paraguariensis) have been investigated qualitatively by LC-MSn. Forty-two chlorogenic acids were detected and all characterized to regioisomeric level on the basis of their fragmentation pattern in tandem MS spectra, 24 of them for the first time from this source. Both chlorogenic acids based on trans- and cis-cinnamic acid substituents were identified. Assignment to the level of individual regioisomers was possible for eight caffeoylquinic acids (1-8), five dicaffeoylquinic acids (20-24), six feruloylquinic acids (9-14), two diferuloyl quinic acids (25 and 26), five p-coumaroylquinic acids (15-19), four caffeoyl-p-coumaroylquinic acids (34-37), seven caffeoyl-feruloylquinic acids (27-33), three caffeoyl-sinapoylquinic acids (38-40), one tricaffeoyl-quinic acid (41), and one dicaffeoyl-feruloylquinic acid (42). Furthermore, four caffeoylshikimates (43-46), three dicaffeoylshikimates (47-49), one tricaffeoylshikimate (51), and one feruloylshikimate (50) have been detected and shown to possess characteristic tandem MS spectra and were assigned by comparison to reference standards.

  DOI：

  10.1021/jf904537z

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.
• Cloning and functional characterization of a p-coumaroyl quinate/shikimate 3′-hydroxylase from potato (Solanum tuberosum)
  作者：Benjamin J. Knollenberg、Jingjing Liu、Shu Yu、Hong Lin、Li Tian

  DOI：10.1016/j.bbrc.2018.01.075

  日期：2018.2

  in tuber yield as well as phenolic metabolites in the core tuber tissue were observed for several AS lines. On the other hand, the AS and control potato lines exhibited similar responses to a bacterial pathogen Pectobacterium carotovorum. These results suggest that StC3'H is implicated in phenolic metabolism in potato. They also suggest that CGA accumulation in the core tissue of potato tubers is an

  绿原酸（CGA）在保护植物免受病原体侵害和促进人类健康方面发挥着重要作用。尽管CGA在马铃薯块茎中积累高水平，但马铃薯中尚未分离出用于CGA生物合成的关键酶对香豆酰奎宁酸/ shi草酸酯3'-羟化酶（C3'H）。在这项工作中，我们从马铃薯中克隆了StC3'H，并表明它分别催化了p-香豆酰基sh草酸酯和p-香豆酰基奎宁酸酯的咖啡酰shi草酸酯和CGA（咖啡酰奎尼酸酯）的形成，但在体外酶中对p-香豆酸没有活性。分析。如果在块茎特异性patatin启动子的控制下，通过反义（AS）抑制作用来阻断StC3'H蛋白的表达，对于几个AS品系，在核心块茎组织中观察到块茎产量以及酚类代谢物的中等变化。另一方面，AS和对照马铃薯品系对细菌病原体胡萝卜腐菌表现出相似的反应。这些结果表明StC3'H与马铃薯的酚类代谢有关。他们还表明，CGA在马铃薯块茎核心组织中的积累是一个复杂受控的过程，另外的C3'H活性也可能与马铃薯的CGA生物合成有关。
• Profiling and Characterization by LC-MS^<i>n</i> of the Chlorogenic Acids and Hydroxycinnamoylshikimate Esters in Maté (Ilex paraguariensis)
  作者：Rakesh Jaiswal、Tina Sovdat、Francesco Vivan、Nikolai Kuhnert

  DOI：10.1021/jf904537z

  日期：2010.5.12

  The chlorogenic acids of mate (Ilex paraguariensis) have been investigated qualitatively by LC-MSn. Forty-two chlorogenic acids were detected and all characterized to regioisomeric level on the basis of their fragmentation pattern in tandem MS spectra, 24 of them for the first time from this source. Both chlorogenic acids based on trans- and cis-cinnamic acid substituents were identified. Assignment to the level of individual regioisomers was possible for eight caffeoylquinic acids (1-8), five dicaffeoylquinic acids (20-24), six feruloylquinic acids (9-14), two diferuloyl quinic acids (25 and 26), five p-coumaroylquinic acids (15-19), four caffeoyl-p-coumaroylquinic acids (34-37), seven caffeoyl-feruloylquinic acids (27-33), three caffeoyl-sinapoylquinic acids (38-40), one tricaffeoyl-quinic acid (41), and one dicaffeoyl-feruloylquinic acid (42). Furthermore, four caffeoylshikimates (43-46), three dicaffeoylshikimates (47-49), one tricaffeoylshikimate (51), and one feruloylshikimate (50) have been detected and shown to possess characteristic tandem MS spectra and were assigned by comparison to reference standards.