3-O-caffeoylshikimic acid | 1178525-55-7

• 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: 3-O-caffeoylshikimic acid
• 英文别名: 3-caffeoylshikimic acid；(3R,4S,5R)-3-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-4,5-dihydroxycyclohexene-1-carboxylic acid
• CAS: 1178525-55-7
• 化学式: C₁₆H₁₆O₈
• 分子量: 336.298
• InChiKey: MRDAXWGGWWDUKL-NFAWXSAZSA-N

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

反应信息

• 作为产物：
  描述：

  在 水 、 三氟乙酸 作用下， 反应 0.5h， 生成 3-O-caffeoylshikimic 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.
• 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.