(S)-4-<(E)-1-formyl-2-(2-furyl)ethenyl>-5-(2-furyl)-2-<(E)-(2-furyl)methylidene>.2,3-dihydro-α-amino-3-oxo-1H-pyrrole-1-acetic acid | 198414-08-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-4-<(E)-1-formyl-2-(2-furyl)ethenyl>-5-(2-furyl)-2-<(E)-(2-furyl)methylidene>.2,3-dihydro-α-amino-3-oxo-1H-pyrrole-1-acetic acid
• 英文别名: (2S)-2-[(5E)-2-(furan-2-yl)-5-(furan-2-ylmethylidene)-3-[(E)-1-(furan-2-yl)-3-oxoprop-1-en-2-yl]-4-oxopyrrol-1-yl]propanoic acid
• CAS: 198414-08-3
• 化学式: C₂₃H₁₇NO₇
• 分子量: 419.39
• InChiKey: WKLHCENPFNYZSQ-SINHFACSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  糠醛 、 L-丙氨酸 以 水 为溶剂， 生成 (S)-2-{4-((E)-1-Formyl-2-furan-2-yl-vinyl)-5-furan-2-yl-2-[1-furan-2-yl-meth-(Z)-ylidene]-3-oxo-2,3-dihydro-pyrrol-1-yl}-propionic acid 、 (S)-4-<(E)-1-formyl-2-(2-furyl)ethenyl>-5-(2-furyl)-2-<(E)-(2-furyl)methylidene>.2,3-dihydro-α-amino-3-oxo-1H-pyrrole-1-acetic acid
  参考文献：
  名称：

  美拉德型反应形成的新型有色1 H-吡咯-3（2 H）-one衍生物化学结构的确定

  摘要：

  报告了先前未知的美拉德反应产物的化学结构的确定，该氨基酸具有掺入四环结构的氨基酸。从呋喃-2-甲醛和L-丙氨酸的热处理水溶液中分离出的红色化合物1a和1b被鉴定为（S）-4 {（E）-1-甲酰基-2-（2-呋喃基）乙烯基} -5-（2-呋喃基）-2-{（E）-（2-呋喃基）亚甲基} -2，3-二氢-α-甲基-3-氧代-1 H-吡咯-1-乙酸及其2-{（Z）-（2-呋喃基）亚甲基}异构体，分别通过几种1D-NMR和2D-NMR技术，MS，UV和IR光谱以及合成实验得到。进行构象分析的2D-NOESY和2D-ROESY实验表明存在两种阻转异构体。

  DOI：

  10.1002/hlca.19970800608

文献信息

• Characterization of the Chemical Structure of Novel Colored Maillard Reaction Products from Furan-2-carboxaldehyde and Amino Acids
  作者：Thomas Hofmann

  DOI：10.1021/jf970732j

  日期：1998.3.1

  Colored compounds formed by Maillard-type reactions from furan-2-carboxaldehyde and primary and secondary amino acids including L-alanine and L-proline, respectively, have been identified. When furan-2-carboxaldehyde was heated with L-proline in aqueous solution at pH 7.0, an intensely yellow compound was generated, which was identified as 5(S)-(2-carboxy-1-pyrrolidinyl)-2-hydroxy-(E,E)-2,4-pentadienal-(S)-(2-carboxypyrrolidine)imine (I) by application of several one- and two-dimensional NMR experiments and, in addition, by MS UV, and IR spectroscopy. Further thermal treatment of compound II resulted, upon a ring closure reaction, in the formation of (E)-4,5-bis[(S)-2-carboxy-1-pyrrolidinyl]-2-cyclopenten-1-one (5), which has been, to our knowledge, as yet not reported in the literature. To confirm the proposed structures, L-proline was substituted by pyrrolidine and piperidine, leading to analogous N-cyanines (2 and 3) and cyclopentenones (4 and 6). On the other hand, thermal treatment of an aqueous solution of furan-2-carboxaldehyde and L-alanine led to the formation of the novel red compounds 8a and Bb, which were identified as (S)-4-[(E)-1-formyl-2-(2-furyl)ethenyl]-5-(2-furyl)-2-[(E)-(2-furyl)methylidene]-2,3-dihydo-alpha-amino-3-oxo-1H-pyrrole-6-acetic acid and the corresponding 2-(Z)-(2-furyl)methylidene isomer. This is the first time that chromophoric compounds comprising four linked rings with an amino acid moiety incorporated were identified in a Maillard reaction system.
• Characterization of the most intense coloured compounds from Maillard reactions of pentoses by application of colour dilution analysis
  作者：Thomas Hofmann

  DOI：10.1016/s0008-6215(98)00279-1

  日期：1998.12

  Thermal treatment of an aqueous solution of xylose and L-alanine in the presence of furan-2-carboxaldehyde, one of the major pentose dehydration products, led to a rapid colorization of the reaction mixture. To characterize the key chromophores formed, a screening procedure, which is based on the determination of the visual threshold of coloured high-performance liquid chromatography (HPLC) fractions, was developed to select the most intense coloured compounds in the complex mixture of Maillard reaction products. This so-called colour dilution analysis (CDA) revealed 20 coloured fractions, amongst which four fractions were evaluated with by far the highest colour impacts. The identification experiments were therefore focused on the compounds evoking the intense colour of these four fractions. Compound 12 was characterized as a mixture of the previously unknown orange-coloured (1R,8aR)- and (1S,8aR)-4-(2-furyl)-7-[(2-furyl)methylidene]-2-hydroxy-2H,7H,8aH-pyrano[2,3-b]pyran-3-one (12a/12b) by several 1D- and 2D-NMR techniques, liquid chromatography-mass spectrometry (LC-MS) as well as UV-Vis spectroscopies. The other three key chromophores 7, 17 and 9 were identified as the yellow coloured 2-[(2-furyl)methylidene]-4-hydroxy-5-methyl-2H-furan-3-one (7), the red coloured 2-[(2-furyl)methylidene]-4-hydroxy-5-[(E)-(2-furyl)methylidene]-methyl-2N-furan-3-one (17) and the red coloured (S)-4-[(E)-1-formyl-2-(2-furyl)ethenyl]-5-(2-furyl)-2-[(E)-(2-furyl)methylidene] 3-dihydo-alpha-amino-3-oxo-1H-pyrrole-1-acetic acid (9). (C) 1998 Elsevier Science Ltd. All rights reserved.