(2E)-3-(4,5-二羟基-2-硝基苯基)丙烯酸 | 402932-81-4

• 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
• 中文名称: (2E)-3-(4,5-二羟基-2-硝基苯基)丙烯酸
• 英文名称: (E)-3-(4,5-dihydroxy-2-nitrophenyl)propenoic acid
• 英文别名: 6-nitrocaffeic acid；(E)-3-(4,5-dihydroxy-2-nitrophenyl)prop-2-enoic acid
• CAS: 402932-81-4
• 化学式: C₉H₇NO₆
• 分子量: 225.158
• InChiKey: HBPNVBRRVZOYHL-OWOJBTEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  甲醇 、 (2E)-3-(4,5-二羟基-2-硝基苯基)丙烯酸 在 氯化亚砜 作用下， 生成 methyl (E)-3-(4,5-dihydroxy-2-nitrophenyl)propenoate
  参考文献：
  名称：

  Reaction of caffeic acid derivatives with acidic nitrite

  摘要：

  Caffeic derivatives were reacted with acidic nitrite at controlled pH in order to mimic the gastric juice conditions. At pH 2, whereas caffeic acid reacts exclusively on the side chain, its esters are readily nitrated. Under more acidic conditions (pH 1), caffeic acid methyl ester undergoes a dimerisation into a norlignan derivative. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(01)00441-5
• 作为产物：
  描述：

  绿原酸 在 Nitrite 作用下， 生成 (2E)-3-(4,5-二羟基-2-硝基苯基)丙烯酸
  参考文献：
  名称：

  Reaction of caffeic acid derivatives with acidic nitrite

  摘要：

  Caffeic derivatives were reacted with acidic nitrite at controlled pH in order to mimic the gastric juice conditions. At pH 2, whereas caffeic acid reacts exclusively on the side chain, its esters are readily nitrated. Under more acidic conditions (pH 1), caffeic acid methyl ester undergoes a dimerisation into a norlignan derivative. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(01)00441-5

文献信息

• New Insights into the Acid-Promoted Reaction of Caffeic Acid and Its Esters with Nitrite:  Decarboxylation Drives Chain Nitrosation Pathways toward Novel Oxime Derivatives and Oxidation/Fragmentation Products Thereof
  作者：Alessandra Napolitano、Marco d'Ischia

  DOI：10.1021/jo015965v

  日期：2002.2.1

  methyl ester (1b) reacted with NO(2)(-) chiefly via ring nitration and/or dimerization to give 5a, the novel nitrated neolignan derivative 10, and the parent 6. Chlorogenic acid (1c) afforded only the ring nitrated derivative 5b. A unifying mechanism for the reaction of 1a and its esters with NO(2)(-) is proposed involving reversible formation of nitroso intermediates via chain nitrosation at the 2-position

  在含有1％甲醇的0.05 M醋酸盐缓冲液（pH 4）中，咖啡酸（1a）（2 x 10（-3）M）与亚硝酸盐（NO（2）（-））（4 x 10（-3）平稳反应M）作为主要产品提供较小的新型2-羟基-和2-甲氧基醛肟7a，b，2-环氧醛肟9a，3,4-二羟基苯甲酸，3,4-二羟基苯甲醛和已知的呋喃喃3c和苯并恶嗪酮4b金额。在较低的1a浓度下（例如1 x 10（-4）M），主要产物为7a，而0.1 m 1a和0.5 M NO（2）（-）3c和9a为主要产物。在pH 2时，7a与3,4-二羟基苯甲醛和一些9a仍然是最丰富的产物，而在pH 1时，9a和3,4-二羟基苯甲醛的产率更高。没有获得关于环硝化产物的证据，包括先前报道的4，5-二羟基-2-硝基苯甲醛。在2 x 10（-3）M浓度和pH 4下 咖啡酸甲酯（1b）主要通过环硝化和/或二聚反应与NO（2）（-）反应生成5a，新型硝化的新木脂素衍生
• Antioxidant properties of nitrocaffeic acids
  作者：Jean-Luc Grenier、Nicole Cotelle、Philippe Cotelle、Jean-Pierre Catteau

  DOI：10.1016/0960-894x(96)00048-0

  日期：1996.2

  A series of nitrodihydroxybenzenes and nitrocaffeic acids were prepared and their hydroxyl radical (OH degrees) and superoxide anion (O-2(-)) scavenging activities and xanthine oxidase inhibition activities were evaluated. 2-Nitrocaffeic acid is the more potent O-2(-) scavenger. 2-(and 5)-Nitrocaffeic acids are the more potent xanthine oxidase inhibitors.
• Synthesis and physico-chemical properties of nitrocaffeic acids
  作者：J. L. Grenier、N. Cotelle、J. P. Catteau、P. Cotelle

  DOI：10.1002/1099-1395(200009)13:9<511::aid-poc283>3.0.co;2-8

  日期：2000.9

  The synthesis and spectroscopic properties of the three isomers of nitrocaffeic acid are described. The three pK(a) s of each isomer were measured by UV-visible spectroscopy. The comparison of the UV-visible spectra of nitrocaffeic acids and those obtained from the reaction of caffeic acid with reactive nitrogen species led to the conclusion that the nitration of caffeic acid with acidic nitrite does not significantly occur and confirmed the absence of nitration when caffeic acid reacts with peroxynitrite. Attempts to obtain free radical species from nitrocaffeic acids by classical methods showed a different reactivity to that of nitroaromatics and catechols. Nitrocaffeic acids do not autoxidize under aqueous basic conditions and are insensitive to t-BuOK or O-2(-.) (two reactants known for their capabilities to oxidize catechols and reduce nitroaromatics). Nitroaromatic anion radicals may be obtained using sodium borohydride as reductant and are particularly stable under an uncontrolled atmosphere. Copyright (C) 2000 John Wiley & Sons, Ltd.