5-caffeoylquinic acid quinone | 877822-89-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-caffeoylquinic acid quinone
• 英文别名: quinone of 5-caffeoylquinic acid；chlorogenic acid quinone；(1S,3R,4R,5R)-3-[(E)-3-(3,4-dioxocyclohexa-1,5-dien-1-yl)prop-2-enoyl]oxy-1,4,5-trihydroxycyclohexane-1-carboxylic acid
• CAS: 877822-89-4
• 化学式: C₁₆H₁₆O₉
• 分子量: 352.298
• InChiKey: ITENTBHADJNDDH-JUHZACGLSA-N

物化性质

• 沸点：
  626.4±55.0 °C(Predicted)
• 密度：
  1.59±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 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：
  158
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  L-半胱氨酸 、 5-caffeoylquinic acid quinone 以 水 为溶剂， 反应 0.5h， 生成 5-cysteinyl-5'-caffeoylquinic acid
  参考文献：
  名称：

  Properties of Chlorogenic Acid Quinone: Relationship between Browning and the Formation of Hydrogen Peroxide from a Quinone Solution

  摘要：

  绿原酸是源自植物的食物中的主要多酚类物质，是一种良好的多酚氧化酶底物。绿原酸醌（CQA-Q）是绿原酸在多酚氧化酶作用下的氧化产物，是酶促褐变中的重要中间化合物。合成了CQA-Q，并研究了其性质以及与褐变的关系。CQA-Q溶液呈黄色或橙色，在酸性水溶液中，其分子吸收系数估计为325 nm波长下为1.7×10³，400 nm波长下为9.7×10²。随着溶液的黄色逐渐褪去，CQA-Q溶液中自发产生了绿原酸和H₂O₂。反应液中的主要产物是淡色聚合物。将赖氨酸和精氨酸等氨基酸添加到CQA-Q溶液中，并没有抑制溶液黄色的褪去。基于这些结果，可以得出结论：CQA-Q本身及其与氨基酸的混合物在酸性水溶液中并未形成强烈的棕色色素。CQA-Q溶液中自发形成了H₂O₂，而其他多酚可能在酶促褐变产生的棕色中发挥了重要作用。

  DOI：

  10.1271/bbb.66.2525
• 作为产物：
  描述：

  (-)-5-咖啡酰奎宁酸 在 sodium periodate 作用下， 以 甲醇 为溶剂， 反应 0.05h， 生成 5-caffeoylquinic acid quinone
  参考文献：
  名称：

  Properties of Chlorogenic Acid Quinone: Relationship between Browning and the Formation of Hydrogen Peroxide from a Quinone Solution

  摘要：

  绿原酸是源自植物的食物中的主要多酚类物质，是一种良好的多酚氧化酶底物。绿原酸醌（CQA-Q）是绿原酸在多酚氧化酶作用下的氧化产物，是酶促褐变中的重要中间化合物。合成了CQA-Q，并研究了其性质以及与褐变的关系。CQA-Q溶液呈黄色或橙色，在酸性水溶液中，其分子吸收系数估计为325 nm波长下为1.7×10³，400 nm波长下为9.7×10²。随着溶液的黄色逐渐褪去，CQA-Q溶液中自发产生了绿原酸和H₂O₂。反应液中的主要产物是淡色聚合物。将赖氨酸和精氨酸等氨基酸添加到CQA-Q溶液中，并没有抑制溶液黄色的褪去。基于这些结果，可以得出结论：CQA-Q本身及其与氨基酸的混合物在酸性水溶液中并未形成强烈的棕色色素。CQA-Q溶液中自发形成了H₂O₂，而其他多酚可能在酶促褐变产生的棕色中发挥了重要作用。

  DOI：

  10.1271/bbb.66.2525

文献信息

• Roles of o-quinones and their polymers in the enzymic browning of apples
  作者：Marie-Aude Rouet-Mayer、Justin Ralambosoa、Jean Philippon

  DOI：10.1016/0031-9422(90)85092-t

  日期：1990.1
• Characterization of polyphenol oxidase in coffee
  作者：Paulo Mazzafera、Simon P Robinson

  DOI：10.1016/s0031-9422(00)00332-0

  日期：2000.10

  Polyphenol oxidase (PPO) was characterized in partially purified extracts of leaves (PPO-L) and fruit endosperm (PPO-E) of coffee (Coffea arabica L.). PPO activity was higher in early developmental stages of both leaves and endosperm of fruits. Wounding or exposure of coffee leaves to methyl jasmonate increased PPO activity 1.5-4-fold. PPO was not latent and was not activated by protease treatment. PPO activity was stimulated 10-15% with sodium dodecyl sulphate (SDS) at 0.35-1.75 mM, but at higher concentrations activities were similar to the control samples, without detergent. Prolonged incubation of extracts with trypsin or proteinase K inhibited PPO activity but pepsin had no effect. Inhibition of PPO with proteinase K was increased in the presence of SDS. PPO activity from both tissues was optimal at pH 6-7 and at an assay temperature of 30 degreesC. Activity was highest with chlorogenic acid as substrate with a K-m of 0.882 mM (PPO-L) and 2.27 mM (PPO-E). Hexadecyl trimethyl-ammonium bromide, polyvinylpyrrolidone 40, cinnamic acid and salicylhydroxamic acid inhibited PPO from both tissues. Both enzymes were inactivated by heat but the activity in endosperm extracts was more heat labile than that from leaves. The apparent M-r, determined by gel filtration was 46 (PPO-L) and 50 kDa(PPO-E). Activity-stained SDS-polyacrylamide gel electrophoresis (PAGE) gels and western blots probed with PPO antibodies suggested the existence of a 67 kDa PPO which is susceptible to proteolytic cleavage that generates a 45 kDa active form. (C) 2000 Elsevier Science Ltd. All-rights reserved.
• Kinetic and Stoichiometry of the Reaction of Chlorogenic Acid and Its Alkyl Esters against the DPPH Radical
  作者：Luis J. López-Giraldo、Mickaël Laguerre、Jérome Lecomte、Maria-Cruz Figueroa-Espinoza、Bruno Baréa、Jochen Weiss、Eric A. Decker、Pierre Villeneuve

  DOI：10.1021/jf803148z

  日期：2009.2.11

  The lipophilization of polar antioxidants such as phenolics is an efficient way to enhance their solubility in apolar media. Thus, in emulsified systems, lipophilized antioxidants are supposed to locate at the lipid/aqueous phase interface and to lead to a better protection of unsaturated lipids. Herein, the antiradical activity of chlorogenic acid (5-CQA) and its corresponding esters with seven fatty alcohols (from methanol to eicosanol) have been achieved using the well-known 2,2-diphenyl-1-picrylhydrazyl (DPPH) method. Hydrophobation was shown to significantly improve the antiradical activity of 5-CQA esters which reached a maximum for butyl- and octyl-chlorogenate. In addition, for both 5-CQA and its esters, it was demonstrated that the global mechanism of DPPH center dot stabilization proceeded likely by electron transfer (ET), while it appeared that the pathways of DPPH center dot stabilization were different between 5-CQA and its esters, as confirmed by the LC-MS characterization of reaction products. Finally, strong differences were found between the tested molecules allowing the proposal of different DPPH center dot stabilization pathways by electron transfer for 5-CQA and its esters.