2,2-bis[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]acetic acid | 246181-58-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 2,2-bis[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]acetic acid
• CAS: 246181-58-8
• 化学式: C₃₂H₂₈O₁₄
• 分子量: 636.566
• InChiKey: ZXVHHFGJNUUEIL-OMICENBGSA-N

物化性质

• 沸点：
  1066.0±65.0 °C(Predicted)
• 密度：
  1.738±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  46
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  258
• 氢给体数：
  11
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  2,2-bis[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]acetic acid 在 水 作用下， 以 乙醇 为溶剂， 生成 NJ2
  参考文献：
  名称：

  通过（+）-儿茶素和乙醛酸之间的反应形成了具有黄蒽骨架的新型多酚化合物。

  摘要：

  在模型溶液系统中研究了（+）-儿茶素与乙醛酸之间的反应。分离出主要的（+）-儿茶素羧甲酰基连接的二聚体，并显示出可制得新的多酚化合物，其在440和460nm附近具有最大吸收。通过孵育8-8个无色异构体获得三种黄色颜料。一种是先前报道的黄蒽化合物NJ2，其最大波长为440 nm。通过将无色二聚体在氢乙醇或甲醇介质中孵育，分别获得了另外两个在460 nm处显示最大吸收的化合物。通过MS和1D和2D NMR技术对这两种新的黄色颜料进行了结构解析，结果表明它们分别是NJ2的乙酯和甲酯。当将NJ2在氢甲醇或乙醇介质中孵育时未获得这些化合物的事实表明，酯化反应是在形成an蒽发色团之前进行的。酯化的无色化合物和相应的x吨中间体的检测证实了推测的机理。还观察到了在560 nm处显示强吸收的新颜料。

  DOI：

  10.1021/jf990424g
• 作为产物：
  描述：

  乙醛酸 、 儿茶提取物 以 乙醇 为溶剂， 反应 2.0h， 生成 2,2-bis[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]acetic acid
  参考文献：
  名称：

  An oxidized tartaric acid residue as a new bridge potentially competing with acetaldehyde in flavan-3-OL condensation

  摘要：

  Iron-induced oxidation of(+)-catechin in a wine-like solution yielded typical products, including colourless and yellow compounds. Structural characterization of the major colourless one indicated that it is a dimer, in which flavanol units are linked through a carboxy-methine bridge. Unlike what might be expected, the structure showed that oxidation does not affect catechin directly, but tartaric acid, to give glyoxylic acid, which then reacts with two flavanol units. From a mechanistic point of view, the reaction resembles, once glyoxylic acid is formed, that of acetaldehyde-induced condensation well documented in enology. Thus, an ion series (up to trimer) was detected by mass spectrometry in the model solution. On the other hand, yellow products formed from colourless ones, especially from that isolated, suggests that a second pathway contributing to browning competes with polycondensation reactions. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0031-9422(97)00276-8

文献信息

• Production and Isomeric Distribution of Xanthylium Cation Pigments and Their Precursors in Wine-like Conditions: Impact of Cu(II), Fe(II), Fe(III), Mn(II), Zn(II), and Al(III)
  作者：Anque Guo、Nikolaos Kontoudakis、Geoffrey R. Scollary、Andrew C. Clark

  DOI：10.1021/acs.jafc.6b05554

  日期：2017.3.22

  This study establishes the influence of Cu(II), Fe(II), Fe(III), Zn(II), Al(III), and Mn(II) on the oxidative production of xanthylium cations from (+)-catechin and either tartaric acid or glyoxylic acid in model wine systems. The reaction was studied at 25 °C using UHPLC and LC-HRMS for the analysis of phenolic products and their isomeric distribution. In addition to the expected products, a colorless

  这项研究建立了Cu（II），Fe（II），Fe（III），Zn（II），Al（III）和Mn（II）对（+）-儿茶素和模型酒系统中的酒石酸或乙醛酸。使用UHPLC和LC-HRMS在25°C下研究了反应，以分析酚类产物及其异构体分布。除预期的产品外，首次检测到暂定为内酯的无色产品。结果表明，Fe离子的重要性和Mn（II）协同作用将酒石酸降解为乙醛酸，而其他金属离子在该机械步骤中的活性最小。Fe（II）和Fe（III）被证明可以介导（+）-儿茶素-乙醛酸加成反应，以前仅归因于Cu（II）。重要的，
• 2D NMR analysis for unambiguous structural elucidation of phenolic compounds formed through reaction between (+)-catechin and glyoxylic acid
  作者：Nour-Eddine Es-Safi、Christine Le Guernevé、Véronique Cheynier、Michel Moutounet

  DOI：10.1002/mrc.1081

  日期：2002.11

  Various phenolic compounds were synthesized in an aqueous–alcoholic solution containing (+)‐catechin and glyoxylic acid which was used as a model of fruit‐derived food browning that usually occurs during aging. After purification by semi‐preparative HPLC, the isolated compounds were subjected to homo‐ and heteronuclear proton and carbon NMR analysis including COSY, TOCSY, ROESY, HSQC and HMBC techniques

  在含有 (+)-儿茶素和乙醛酸的水-醇溶液中合成了各种酚类化合物，该溶液用作通常在老化过程中发生的水果衍生食物褐变的模型。通过半制备型 HPLC 纯化后，分离出的化合物进行同核和异核质子和碳核磁共振分析，包括 COSY、TOCSY、ROESY、HSQC 和 HMBC 技术。这些实验允许对分离的化合物进行结构解析和完整的 1H 和 13C NMR 分配。除了确定连接位点之外，还讨论了分配所有质子和碳共振所遵循的策略。版权所有 © 2002 John Wiley & Sons, Ltd.
• Structure of a new xanthylium salt derivative
  作者：Nour-Eddine Es-Safi、Christine Le Guerneve´、Benoiˆt Labarbe、He´le`ne Fulcrand、Ve´ronique Cheynier、Michel Moutounet

  DOI：10.1016/s0040-4039(99)01156-9

  日期：1999.8

  A new polyphenolic compound with a xanthylium skeleton has been synthesised from (+)-catechin and glyoxylic acid. its structural elucidation was achieved by UV, MS and NMR spectroscopies. Its formation involved glyoxylic acid-mediated dimerisation of(+)-catechin 1 giving thus compound 2, followed by cyclisation to a xanthene derivative 3 which by oxidation afforded the xanthylium compound 4. The detection and structural determination of the xanthene compound confirmed the postulated mechanism. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.
• Role of Aldehydic Derivatives in the Condensation of Phenolic Compounds with Emphasis on the Sensorial Properties of Fruit-Derived Foods
  作者：Nour-Eddine Es-Safi、Véronique Cheynier、Michel Moutounet

  DOI：10.1021/jf025503y

  日期：2002.9.1

  The reactions between (epi)catechin mavidin 3 O-glucoside and some aldehydes were investigated by LC/DAD and LC/ESI MS analysis. The obtained results showed that the acetaldehyde mediated condensation occurred more generally and glyoxylic acid furfural and 5 (hydroxymethyl)furfural (HMF) react in the same way in the first stages of the reactions. In terms of reactivity, reactions were faster with acetaldehyde than with glyoxylic acid furfural or HMF where the reactions were slower. In the case of acetaldehyde, the obtained purple derivatives were more predominant and stable than the colorless adducts and no xanthylium salt was detected. Interactions involving glyoxylic acid yield purple adducts which were obtained in small amount compared to the colorless ones. The latter were shown to proceed to more polymerized and yellowish derivatives. Finally, in the case of furfural and HMF purple compounds involving flavanol and anthocyanin units were detected and colorless compounds were shown to be predominant and to yield yellowish xanthylium salts.