N-caffeoyl-4,5-dihydroxyanthranilic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-caffeoyl-4,5-dihydroxyanthranilic acid
• 英文别名: 2-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]amino]-4,5-dihydroxybenzoic acid
• 化学式: C₁₆H₁₃NO₇
• 分子量: 331.282
• InChiKey: NSMQGHHMENFETF-DUXPYHPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  147
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  TRANS-咖啡酸 在 碳酸氢钠 、 N,N'-二环己基碳二亚胺 作用下， 以 水 、 丙酮 为溶剂， 反应 24.0h， 生成 N-caffeoyl-4,5-dihydroxyanthranilic acid
  参考文献：
  名称：

  New series of avenanthramides in oat seed

  摘要：

  燕麦籽中的燕麦苷是其特有的成分。我们通过高效液相色谱法分析了燕麦籽的甲醇提取物，检测到三种化合物1、2和3，它们在保留时间上与燕麦苷相似。通过柱层析和高效液相色谱法纯化了这三种化合物。对1、2和3的光谱分析表明，它们分别是4,5-二羟基蒽醌酸与咖啡酸、对香豆酸和香草酸的酰胺。通过将4,5-二羟基蒽醌酸和羟基肉桂酸类的N-羟基琥珀酰亚胺酯合成的化合物与光谱和色谱行为进行比较，证实了它们的身份。多反应监测的LC-MS/MS分析表明，1、2和3的含量是相应燕麦苷的16.5-26.9%，这些燕麦苷含有5-羟基蒽醌酸。化合物1、2和3的2,2-二苯基-1-芘肼（DPPH）自由基清除活性比含有5-羟基蒽醌酸的相应燕麦苷更强，表明4,5-二羟基蒽醌酸基团参与了清除DPPH自由基的过程。

  DOI：

  10.1080/09168451.2014.946390

文献信息

• METHOD FOR INCREASING CONCENTRATION OF AVENANTHRAMIDES IN OATS
  申请人：Collins Frank William

  公开号：US20120082740A1

  公开（公告）日：2012-04-05

  Methods for increasing the levels of avenanthramides in oats through false malting is disclosed. Oats are first subject to induction or enhancement of a secondary dormancy, and then malted for up to 5 days at an elevated temperature. The malted but not germinated oats are then dried and used as is, or further processed or milled to produce food, feed, nutraceutical or personal care products and ingredients. Methods are also provided for rendering non-dormant oats dormant and thus suitable for false malting.
• New series of avenanthramides in oat seed
  作者：Atsushi Ishihara、Kana Kojima、Takeshi Fujita、Yuya Yamamoto、Hiromitsu Nakajima

  DOI：10.1080/09168451.2014.946390

  日期：2014.12.2

  Avenanthramides are characteristic constituents of oat seeds. We analyzed the methanol extract of oat seeds by HPLC and detected three compounds 1, 2, and 3 eluted at retention times similar to avenanthramides. The three compounds were purified by column chromatography and HPLC. Spectroscopic analyses of 1, 2, and 3 suggested that they are amides of 4,5-dihydroxyanthranilic acid with caffeic, p-coumaric, and ferulic acids, respectively. Their identities were confirmed by comparing spectra and chromatographic behavior with compounds synthesized from 4,5-dihydroxyanthranilic acid and N-hyrdroxysuccinimide esters of hydroxycinnamic acids. LC-MS/MS analysis with multiple reaction monitoring showed that the amounts of 1, 2, and 3 were 16.5–26.9% of corresponding avenanthamides with 5-hydroxyanthranilic acid. Compounds 1, 2, and 3 showed stronger 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical-scavenging activity than the corresponding avenanthramides with 5-hydroxyanthranilic acid, indicating the involvement of 4,5-dihydroxyanthranilic acid moiety in the scavenging of DPPH radicals.

  燕麦籽中的燕麦苷是其特有的成分。我们通过高效液相色谱法分析了燕麦籽的甲醇提取物，检测到三种化合物1、2和3，它们在保留时间上与燕麦苷相似。通过柱层析和高效液相色谱法纯化了这三种化合物。对1、2和3的光谱分析表明，它们分别是4,5-二羟基蒽醌酸与咖啡酸、对香豆酸和香草酸的酰胺。通过将4,5-二羟基蒽醌酸和羟基肉桂酸类的N-羟基琥珀酰亚胺酯合成的化合物与光谱和色谱行为进行比较，证实了它们的身份。多反应监测的LC-MS/MS分析表明，1、2和3的含量是相应燕麦苷的16.5-26.9%，这些燕麦苷含有5-羟基蒽醌酸。化合物1、2和3的2,2-二苯基-1-芘肼（DPPH）自由基清除活性比含有5-羟基蒽醌酸的相应燕麦苷更强，表明4,5-二羟基蒽醌酸基团参与了清除DPPH自由基的过程。