methylene reductinic acid | 83840-90-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯基酸
• 英文名称: methylene reductinic acid
• 英文别名: 2,3-dihydroxy-4-methylene-2-cyclopentene-1-one；2,3-Dihydroxy-4-methylidenecyclopent-2-en-1-one；2,3-dihydroxy-4-methylidenecyclopent-2-en-1-one
• CAS: 83840-90-8
• 化学式: C₆H₆O₃
• 分子量: 126.112
• InChiKey: NNCQFFKUDONSBM-UHFFFAOYSA-N

物化性质

• 沸点：
  274.3±40.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  糠醛 、 methylene reductinic acid 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以38%的产率得到3-hydroxy-4-<(E)-(2-furyl)methylidene>methyl-3-cyclopentene-1,2-dione
  参考文献：
  名称：

  AcetylformoinA Chemical Switch in the Formation of Colored Maillard Reaction Products from Hexoses and Primary and Secondary Amino Acids

  摘要：

  Thermal treatment of a methanolic solution of N-(1-deoxy-D-fructos-1-yl)-L-proline and furan-2-carboxaldehyde led to the rapid formation of colored compounds, among which 4-hydroxy-2-methoxy-2-methyl-5-[(E)-(2-furyl)methylidene]methyl-2H-furan-3-one (1) could be identified as one of the main colored compounds by NMR, LC/MS, and UV-vis spectroscopy. Studies on its formation revealed that condensation of the hexose dehydration product acetylformoin (2a/2b) with furan-2-carboxaldehyde formed the labile 2,4-hydroxy-2-methyl-5-[(E)-(2-furyl)methylidene]methyl-2H-furan-3-one (3a/3b), which then reacts with methanol to the more stable colorant 1. Reacting furan-2-carboxaldehyde with N-(1-deoxy-D-fructos-1-yl)-L-alanine, however, completely stalled the formation of acetylformoin and, consequently, also of colorant 1. Further model studies revealed acetylformoin as a chemical snitch in the Maillard reaction determining different reaction pathways in the presence of primary and secondary amino acids; for example, the reaction with glycine methyl ester and glycine revealed 2,4-dihydroxy-2,5-dimethyl-1-methoxycarbonylmethyl- (4) and 2,4-dihydroxy-2,5-dimethyl-1-carboxymethyl -3-oxo-2H-pyrrole (5), respectively, whereas the reaction with L-proline resulted in the formation of pyrrolidino- (6) and bispyrrolidino-hexose-reductone (7). Dry heating of these amino reductones in the presence of furan-2-carboxaldehyde produced the colorants 2,4-dihydroxy-2-methyl-5-[(E)-(2-furyl)methylidene]methyl-1-methoxycarbonylmethyl-3-oxo-2H-pyrrole (8) from 4 and 3-hydroxy-4-[(E)-(2-furyl)methylidene] methyl-3-cyclopentene-1,2-dione (9) from 6 and 7. Quantitative studies revealed 3-hydroxy-4-methyl-3-cyclopentene-1,2-dione (10) and methylene-reductinic acid (11) as the key intermediates in the formation of colorant 9.

  DOI：

  10.1021/jf980512l
• 作为产物：
  描述：

  3,4-二羟基-3-己烯-2,5-二酮 在 盐酸 作用下， 以 水 为溶剂， 反应 0.34h， 生成 methylene reductinic acid
  参考文献：
  名称：

  Studies on the inhibition of tumor cell growth and microtubule assembly by 3-hydroxy-4-[(E)-(2-furyl)methylidene]methyl-3-cyclopentene-1,2-dione, an intensively coloured Maillard reaction product

  摘要：

  Very recently, 3-hydroxy-4-[(E)-(2-furyl)methylidene]methyl-3-cyclopentene-1,2-dione (1) has been successfully identified as an intensively coloured Maillard product formed from glucose and L-proline upon thermal food processing. Using a biomimetic synthetic strategy, reference material of compound 1 was prepared and purified, and then used to study its effect on the growth of human tumor cells. Compound 1 was found to potently inhibit the growth of human tumor cells in vitro. Using a reporter gene assay we could show that in growth inhibitory concentrations compound 1 effectively inhibits the phosphorylation of the transcription factor Elk-1. In addition, 1 was found to affect the microtubule skeleton. The human mammary carcinoma cell line MCF-7 exhibits a decrease of the microtubule organisation. when treated for 24 h with 1 (greater than or equal to 20 muM). At concentrations of 30 muM and above a loss of microtubule integrity is observed after 1 h incubation. In vitro studies demonstrated that the polymerisation and, to a minor extent, also the depolymerisation of tubulin, isolated and purified from bovine brain, is inhibited in a dose-dependent manner at concentrations of 30 muM and above. This is the first time that a non-enzymatically formed browning compound of known structure was reported to effectively inhibit tumor cell growth and microtubule assembly. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0278-6915(01)00093-x

文献信息

• AcetylformoinA Chemical Switch in the Formation of Colored Maillard Reaction Products from Hexoses and Primary and Secondary Amino Acids
  作者：Thomas Hofmann

  DOI：10.1021/jf980512l

  日期：1998.10.1

  Thermal treatment of a methanolic solution of N-(1-deoxy-D-fructos-1-yl)-L-proline and furan-2-carboxaldehyde led to the rapid formation of colored compounds, among which 4-hydroxy-2-methoxy-2-methyl-5-[(E)-(2-furyl)methylidene]methyl-2H-furan-3-one (1) could be identified as one of the main colored compounds by NMR, LC/MS, and UV-vis spectroscopy. Studies on its formation revealed that condensation of the hexose dehydration product acetylformoin (2a/2b) with furan-2-carboxaldehyde formed the labile 2,4-hydroxy-2-methyl-5-[(E)-(2-furyl)methylidene]methyl-2H-furan-3-one (3a/3b), which then reacts with methanol to the more stable colorant 1. Reacting furan-2-carboxaldehyde with N-(1-deoxy-D-fructos-1-yl)-L-alanine, however, completely stalled the formation of acetylformoin and, consequently, also of colorant 1. Further model studies revealed acetylformoin as a chemical snitch in the Maillard reaction determining different reaction pathways in the presence of primary and secondary amino acids; for example, the reaction with glycine methyl ester and glycine revealed 2,4-dihydroxy-2,5-dimethyl-1-methoxycarbonylmethyl- (4) and 2,4-dihydroxy-2,5-dimethyl-1-carboxymethyl -3-oxo-2H-pyrrole (5), respectively, whereas the reaction with L-proline resulted in the formation of pyrrolidino- (6) and bispyrrolidino-hexose-reductone (7). Dry heating of these amino reductones in the presence of furan-2-carboxaldehyde produced the colorants 2,4-dihydroxy-2-methyl-5-[(E)-(2-furyl)methylidene]methyl-1-methoxycarbonylmethyl-3-oxo-2H-pyrrole (8) from 4 and 3-hydroxy-4-[(E)-(2-furyl)methylidene] methyl-3-cyclopentene-1,2-dione (9) from 6 and 7. Quantitative studies revealed 3-hydroxy-4-methyl-3-cyclopentene-1,2-dione (10) and methylene-reductinic acid (11) as the key intermediates in the formation of colorant 9.
• Studies on the inhibition of tumor cell growth and microtubule assembly by 3-hydroxy-4-[(E)-(2-furyl)methylidene]methyl-3-cyclopentene-1,2-dione, an intensively coloured Maillard reaction product
  作者：D Marko、M Kemény、E Bernady、M Habermeyer、U Weyand、S Meiers、O Frank、T Hofmann

  DOI：10.1016/s0278-6915(01)00093-x

  日期：2002.1

  Very recently, 3-hydroxy-4-[(E)-(2-furyl)methylidene]methyl-3-cyclopentene-1,2-dione (1) has been successfully identified as an intensively coloured Maillard product formed from glucose and L-proline upon thermal food processing. Using a biomimetic synthetic strategy, reference material of compound 1 was prepared and purified, and then used to study its effect on the growth of human tumor cells. Compound 1 was found to potently inhibit the growth of human tumor cells in vitro. Using a reporter gene assay we could show that in growth inhibitory concentrations compound 1 effectively inhibits the phosphorylation of the transcription factor Elk-1. In addition, 1 was found to affect the microtubule skeleton. The human mammary carcinoma cell line MCF-7 exhibits a decrease of the microtubule organisation. when treated for 24 h with 1 (greater than or equal to 20 muM). At concentrations of 30 muM and above a loss of microtubule integrity is observed after 1 h incubation. In vitro studies demonstrated that the polymerisation and, to a minor extent, also the depolymerisation of tubulin, isolated and purified from bovine brain, is inhibited in a dose-dependent manner at concentrations of 30 muM and above. This is the first time that a non-enzymatically formed browning compound of known structure was reported to effectively inhibit tumor cell growth and microtubule assembly. (C) 2001 Elsevier Science Ltd. All rights reserved.