4-hydroxy-2-[13C]methyl-5-methyl-3(2H)-furanone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 4-hydroxy-2-[13C]methyl-5-methyl-3(2H)-furanone
• 英文别名: Furaneol(13C6) 99%；4-hydroxy-5-methyl-2-(113C)methylfuran-3-one
• 化学式: C₆H₈O₃
• 分子量: 129.117
• InChiKey: INAXVXBDKKUCGI-OUBTZVSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  D-吡喃木糖 、 甘氨酸-2-13C 在 phosphate buffer pH 6.0 作用下， 反应 1.0h， 生成 4-hydroxy-2-[13C]methyl-5-methyl-3(2H)-furanone
  参考文献：
  名称：

  Formation of 4-Hydroxy-2,5-dimethyl-3(2H)-furanone and 4-Hydroxy-2(or 5)-ethyl-5(or 2)-methyl-3(2H)-furanone through Maillard Reaction Based on Pentose Sugars

  摘要：

  The caramel-like smelling compounds 4-hydroxy-2,5-dimethyl-3(2H)-furanone (HDMF) and 4-hydroxy-2(or 5)-ethyl-5(or 2)-methyl-3(2H)-furanone (HEMF) were identified by GC-MS and GC-MS/MS in Maillard reaction systems based on pentoses. The reaction was performed in a phosphate buffer by heating xylose, ribose, or arabinose with glycine or L-alanine at 90 degrees C for 1 h. HEMF was detected in the system pentose/alanine. HDMF was formed in both pentose/glycine and pentose/alanine systems as well as directly from pentoses. Experiments using C-13-labeled glycine and alanine suggest the incorporation of the Strecker degradation products formaldehyde and acetaldehyde into the pentose moiety, forming the furanones HDMF and HEMF, respectively. The presence of C-12-HDMF, which was approximately 30% of the total HDMF amount found in xylose/glycine, indicates that HDMF is partly formed by sugar fragmentation. The proposed mechanism for the formation of the furanones is based on decomposition of the Amadori compound via 2,3-enolization, chain elongation by the Strecker aldehydes, and reduction of the resulting acetylformoin-type intermediates to the target molecules.

  DOI：

  10.1021/jf950439o

文献信息

• Formation of 4-Hydroxy-2,5-dimethyl-3(2<i>H</i>)-furanone and 4-Hydroxy-2(or 5)-ethyl-5(or 2)-methyl-3(2<i>H</i>)-furanone through Maillard Reaction Based on Pentose Sugars
  作者：Imre Blank、Laurent B. Fay

  DOI：10.1021/jf950439o

  日期：1996.1.1

  The caramel-like smelling compounds 4-hydroxy-2,5-dimethyl-3(2H)-furanone (HDMF) and 4-hydroxy-2(or 5)-ethyl-5(or 2)-methyl-3(2H)-furanone (HEMF) were identified by GC-MS and GC-MS/MS in Maillard reaction systems based on pentoses. The reaction was performed in a phosphate buffer by heating xylose, ribose, or arabinose with glycine or L-alanine at 90 degrees C for 1 h. HEMF was detected in the system pentose/alanine. HDMF was formed in both pentose/glycine and pentose/alanine systems as well as directly from pentoses. Experiments using C-13-labeled glycine and alanine suggest the incorporation of the Strecker degradation products formaldehyde and acetaldehyde into the pentose moiety, forming the furanones HDMF and HEMF, respectively. The presence of C-12-HDMF, which was approximately 30% of the total HDMF amount found in xylose/glycine, indicates that HDMF is partly formed by sugar fragmentation. The proposed mechanism for the formation of the furanones is based on decomposition of the Amadori compound via 2,3-enolization, chain elongation by the Strecker aldehydes, and reduction of the resulting acetylformoin-type intermediates to the target molecules.