[E/Z]-1,2-bis(2-furyl)-1-pentene-3,4-dione | 83684-93-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [E/Z]-1,2-bis(2-furyl)-1-pentene-3,4-dione
• 英文别名: 4,5-bis(furan-2-yl)pent-4-ene-2,3-dione
• CAS: 83684-93-9
• 化学式: C₁₃H₁₀O₄
• 分子量: 230.22
• InChiKey: ZTPUKMKYNKCMHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.57
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  60.42
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  [E/Z]-1,2-bis(2-furyl)-1-pentene-3,4-dione 以 甲醇 、 水 为溶剂， 反应 1.0h， 以15%的产率得到4,5-bis(2-furyl)-2-methyl-3H-furan-2-one
  参考文献：
  名称：

  Characterization of Key Chromophores Formed by Nonenzymatic Browning of Hexoses and l-Alanine by Using the Color Activity Concept

  摘要：

  Thermal treatment of an aqueous solution of D-glucose and L-alanine in the presence of the carbohydrate degradation product furan-2-aldehyde resulted in the formation of a variety of colored compounds, among which (Z)-2-[(2-furyl)methylidene]-5,6-di(2-furyl)-6H-pyran-3-one (I), [E]- and [Z]-1,2-bis(2-furyl)-1-pentene-3,4-dione (IIa/IIb), 4,5-bis(2-furyl)-2-methyl-3H-furan-2-one (III), and (S,S)- and (SR)-2-[4,5-bis(2-furyl)-2-hydroxy-2-methyl-3(2H)-pyrrol-1-yl]propionic acid (IVa/IVb) as well as 2-[(2-furyl)methylidene]-4-hydroxy-5-[(E)-(2-furyl)methylidene]methyl-2H-furan-3-one (V) were successfully identified as the most intense by application of the color dilution analysis. To measure the contribution of these colorants to the overall color of the browned Maillard mixture, color activity values were calculated as the ratio of the concentration to the visual detection threshold of each colorant. By application of this color activity concept, 16.0% of the overall color of the Maillard mixture accounted for these five types of colorants, thus confirming them as key chromophores. On the basis of synthetic model experiments, the formation pathways leading to the chromophores IIa/IIb, III, and IVa/IVb were proposed.

  DOI：

  10.1021/jf0001987
• 作为产物：
  描述：

  糠醛 、 羟基丙酮 在 哌啶乙酸盐 作用下， 以 乙醇 、 水 为溶剂， 反应 0.58h， 以2%的产率得到[E/Z]-1,2-bis(2-furyl)-1-pentene-3,4-dione
  参考文献：
  名称：

  Characterization of Key Chromophores Formed by Nonenzymatic Browning of Hexoses and l-Alanine by Using the Color Activity Concept

  摘要：

  Thermal treatment of an aqueous solution of D-glucose and L-alanine in the presence of the carbohydrate degradation product furan-2-aldehyde resulted in the formation of a variety of colored compounds, among which (Z)-2-[(2-furyl)methylidene]-5,6-di(2-furyl)-6H-pyran-3-one (I), [E]- and [Z]-1,2-bis(2-furyl)-1-pentene-3,4-dione (IIa/IIb), 4,5-bis(2-furyl)-2-methyl-3H-furan-2-one (III), and (S,S)- and (SR)-2-[4,5-bis(2-furyl)-2-hydroxy-2-methyl-3(2H)-pyrrol-1-yl]propionic acid (IVa/IVb) as well as 2-[(2-furyl)methylidene]-4-hydroxy-5-[(E)-(2-furyl)methylidene]methyl-2H-furan-3-one (V) were successfully identified as the most intense by application of the color dilution analysis. To measure the contribution of these colorants to the overall color of the browned Maillard mixture, color activity values were calculated as the ratio of the concentration to the visual detection threshold of each colorant. By application of this color activity concept, 16.0% of the overall color of the Maillard mixture accounted for these five types of colorants, thus confirming them as key chromophores. On the basis of synthetic model experiments, the formation pathways leading to the chromophores IIa/IIb, III, and IVa/IVb were proposed.

  DOI：

  10.1021/jf0001987

文献信息

• Characterization of Key Chromophores Formed by Nonenzymatic Browning of Hexoses and <scp>l</scp>-Alanine by Using the Color Activity Concept
  作者：Oliver Frank、Thomas Hofmann

  DOI：10.1021/jf0001987

  日期：2000.12.1

  Thermal treatment of an aqueous solution of D-glucose and L-alanine in the presence of the carbohydrate degradation product furan-2-aldehyde resulted in the formation of a variety of colored compounds, among which (Z)-2-[(2-furyl)methylidene]-5,6-di(2-furyl)-6H-pyran-3-one (I), [E]- and [Z]-1,2-bis(2-furyl)-1-pentene-3,4-dione (IIa/IIb), 4,5-bis(2-furyl)-2-methyl-3H-furan-2-one (III), and (S,S)- and (SR)-2-[4,5-bis(2-furyl)-2-hydroxy-2-methyl-3(2H)-pyrrol-1-yl]propionic acid (IVa/IVb) as well as 2-[(2-furyl)methylidene]-4-hydroxy-5-[(E)-(2-furyl)methylidene]methyl-2H-furan-3-one (V) were successfully identified as the most intense by application of the color dilution analysis. To measure the contribution of these colorants to the overall color of the browned Maillard mixture, color activity values were calculated as the ratio of the concentration to the visual detection threshold of each colorant. By application of this color activity concept, 16.0% of the overall color of the Maillard mixture accounted for these five types of colorants, thus confirming them as key chromophores. On the basis of synthetic model experiments, the formation pathways leading to the chromophores IIa/IIb, III, and IVa/IVb were proposed.