1,3-bis{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-4,5-dihydroxycyclohexanecarboxylic acid | 251320-66-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3-bis{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-4,5-dihydroxycyclohexanecarboxylic acid
• 英文别名: 1,3‐O‐dicaffeoylquinic acid；1-trans,5-trans-dicaffeoylquinic acid；1,5-O-trans-dicaffeoylquinic acid；1,3-O-dicaffeoyl-quinic acid-；1,3-di-O-caffeoylquinic acid；1,5-O-di-caffeoylquinic acid；1,3-Dicaffeoylquinic acid；(1S,3R,4R,5R)-1,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-4,5-dihydroxycyclohexane-1-carboxylic acid
• CAS: 251320-66-8
• 化学式: C₂₅H₂₄O₁₂
• 分子量: 516.458
• InChiKey: YDDUMTOHNYZQPO-PSEXTPKNSA-N

物化性质

• 沸点：
  819.9±65.0 °C(Predicted)
• 密度：
  1?+-.0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  211
• 氢给体数：
  7
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  1,3-bis{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-4,5-dihydroxycyclohexanecarboxylic acid 在 ammonium hydroxide 作用下， 反应 2.0h， 以56%的产率得到1,3-di-O-caffeoylquinic acid
  参考文献：
  名称：

  New and facile method of preparation of the anti-HIV-1 agent, 1,3-dicaffeoylquinic acid

  摘要：

  A facile and inexpensive preparation of 1,3-dicaffeoylquinic acid (cynarin) from the leaves Cynara cardunculus L. (Asteraceae) without the use of any chromatographic steps is described. The procedure is based on separation of the fraction rich in 1,5-dicaffeoylquinic acid, isomerisation of 1,5-dicaffeoylquinic acid to cynarin and, owing to its higher polarity, the simple isolation of cynarin from the reaction mixture. Cynarin inhibited HIV-1 replication in MT-2 cell culture at non-toxic concentrations similar to other previously tested dicaffeoylquinic acids, which have been recently established as a potent and highly selective class of HIV-1 integrase inhibitors. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00448-8

文献信息

• 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
• Methods for making yerba mate extract composition
  申请人：CARGILL, INCORPORATED

  公开号：US11351214B2

  公开（公告）日：2022-06-07

  Methods are described herein for making a composition comprising at least one of caffeic acid, monocaffeoylquinic acids, and dicaffeoylquinic acids, and salts thereof.

  本文描述了制作包含至少一种咖啡酸、单咖啡酰奎宁酸和二咖啡酰奎宁酸及其盐的组合物的方法。
• Methods for making botanical extract composition
  申请人：CARGILL, INCORPORATED

  公开号：US11344596B2

  公开（公告）日：2022-05-31

  A method for making a caffeoylquinic composition from a botanical source is disclosed. The method may include chromatographing an extract of biomass on an ion exchange stationary phase and obtaining an eluent comprising a caffeoylquinic composition. The biomass may be Stevia or yerba mate, for example. The caffeoylquinic composition includes one or more of monocaffeoylquinic acid, dicaffeoylquinic acid, and salts of the foregoing.

  本发明公开了一种利用植物源制造咖啡酰奎宁酸组合物的方法。该方法可包括在离子交换固定相上对生物质提取物进行色谱分析，并获得包含咖啡酰奎宁酸组合物的洗脱液。生物质可以是甜叶菊或耶巴马黛茶等。咖啡酰奎宁酸组合物包括单咖啡酰奎宁酸、二咖啡酰奎宁酸和上述物质的盐中的一种或多种。
• Dicaffeolyquinic acids from Helichrysum italicum and Achillea cartilaginea
  作者：G. G. Zapesochnaya、V. A. Kurkin、T. V. Kudryavtseva、B. S. Karasartov、K. S. Cholponbaev、N. A. Tyukavkina、V. E. Ruchkin

  DOI：10.1007/bf00629790

  日期：——
• STEVIOL GLYCOSIDE SOLUBILITY ENHANCERS
  申请人：CARGILL, INCORPORATED

  公开号：US20190223481A1

  公开（公告）日：2019-07-25

  A solubilized steviol glycoside composition including one or more steviol glycosides and one or more steviol glycoside solubility enhancers can be used as a sweetener composition to sweeten other compositions (sweetenable compositions) such as foods, beverages, medicines, oral hygiene compositions, pharmaceuticals, nutraceuticals, and the like.