2-<(2-furyl)methylidene>-4-hydroxy-5-methyl-2H-furan-3-one

• 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: 2-<(2-furyl)methylidene>-4-hydroxy-5-methyl-2H-furan-3-one
• 英文别名: (2E)-2-(furan-2-ylmethylidene)-4-hydroxy-5-methylfuran-3-one
• 化学式: C₁₀H₈O₄
• 分子量: 192.171
• InChiKey: HZEOCEIZZAJEGD-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  异恶唑，3-isocyanato-5-(1-methylethyl)-(9CI) 在 phopshate buffer pH 6.0 、 DL-丙氨酸 作用下， 反应 2.5h， 以12 mg的产率得到2-<(2-furyl)methylidene>-4-hydroxy-5-methyl-2H-furan-3-one
  参考文献：
  名称：

  Identification of Novel Colored Compounds Containing Pyrrole and Pyrrolinone Structures Formed by Maillard Reactions of Pentoses and Primary Amino Acids

  摘要：

  Heating of pentoses with alanine in a ratio of 10:1 in aqueous solution at pH 7.0 generated the yellow 2-[(2-furyl)methylidene]-4-hydroxy-5-methyl-2H-furan-3-one (1), being well in line with data reported in the literature. Decreasing the relative concentrations of the pentose produced further colored nitrogen-containing compounds, among which (S)-4-hydroxy-5-methyl-2-[N-(1'-carboxyethyl)-pyrrolyl-2-methyldiene]-2H-furan-3-one (2) could be identified by spectroscopic and synthetic experiments. On the other hand, thermal treatment of an aqueous solution of pentose and L-alanine in the presence of furan-2-carboxaldehyde led to the formation of the novel red (2R)-4-oxo-3,5-bis-[(2-furyl)methylidene] tetrahydropyrrolo[1,2-c]-5(S)-(2-furyl)oxazolidine and its 5(R)-(2-furyl)oxazolidine diasteromer (3a/3b), which were characterized by several 1D- and 2D-NMR techniques, LC/MS, and UV-vis spectroscopy as well as by synthesis of the chromophoric substructure. In addition, the red compounds (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-1-acetic acid (4b) and the corresponding 2-[(Z)-(2-furyl)-methylidene] isomer (4b) were identified in this Maillard mixture. Quantitative studies on the formation of these colorants clearly demonstrates the key role of 3-deoxypentos-2-ulose as an intermediate in the formation of 4a/4b. Reaction pathways leading to the colorants 2, 3a/3b, and 4a/4b from pentoses and alanine are discussed.

  DOI：

  10.1021/jf980477i

文献信息

• Identification of New Heterocyclic Nitrogen Compounds from Glucose-Lysine and Xylose-Lysine Maillard Model Systems
  作者：Richard G. Bailey、Jennifer M. Ames、John Mann

  DOI：10.1021/jf000722+

  日期：2000.12.1

  Aqueous sugar (glucose or xylose)-lysine model systems were heated at 80 degreesC for 6 h with the pH maintained at a predetermined value (3, 4, or 5). Selected compounds were isolated by combinations of solvent extraction and semipreparative HPLC, prior to identification by NMR and mass spectrometry. Two compounds were identified from the pH 5 glucose system and were identified as epsilon-[2-formyl-5-(hydroxymethyl)pyrrole-1-yl]-L-norleucine (pyrraline) and the new compound, 1-(5-carboxy-5-aminopentyl)-2-formyl-3-(1,2,3 -trihydroxypropyl)pyrrole. A third compound was partially characterized. 2-Acetyl-5-hydroxymethyl-5,6-dihydro-4H-pyridinone was identified in the pH 3 xylose system, and the new compound, 8-furan-2-yl-methyl-5-hydroxymethyl-5,6 dione, was identified in the pH 4 xylose system. 2-Furfurylidene-4-hydroxy-5-methyl-3(2H) was identified in both xylose systems. Mechanisms of formation are proposed for the novel compounds.
• 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.
• ADVANCED GLYCATION END PRODUCTS AS ACTIVE INGREDIENTS
  申请人：Huchel Ursula

  公开号：US20100204176A1

  公开（公告）日：2010-08-12

  Cosmetic composition comprising at least one compound from advanced glycation end products (‘AGEs’) and/or precursors thereof as an agent for skin treatment, especially for protection and/or care of the skin. The present invention further provides a cosmetic composition comprising at least one compound from the group of the AGEs and/or precursors thereof, wherein the AGEs are prepared by reacting sugars with the amino acids lysine and/or arginine.
• US8202892B2
  申请人：——

  公开号：US8202892B2

  公开（公告）日：2012-06-19
• [DE] ADVANCED GLYCATION ENDPRODUCTS ALS WIRKSTOFFE<br/>[EN] ADVANCED GLYCATION END PRODUCTS AS ACTIVE INGREDIENTS<br/>[FR] PRODUITS FINAUX DE LA GLYCOSYLATION AVANCÉE EN TANT QUE SUBSTANCES ACTIVES
  申请人：HENKEL AG & CO KGAA

  公开号：WO2009007257A2

  公开（公告）日：2009-01-15

  Die vorliegende Erfindung betrifft die Verwendung einer kosmetischen Zusammensetzung enthaltend mindestens eine Verbindung aus der Gruppe der AGEs (Advanced Glycation Endproducts) und/oder deren Vorläufern als Mittelzur Hautbehandlung, insbesondere zum Schutz und/oder zur Pflege der Haut.Gegenstand der vorliegenden Erfindung ist weiterhin eine kosmetische Zusammensetzung enthaltend mindestens eine Verbindung aus der Gruppe der AGEs und/oder deren Vorläufern, wobei die AGEs durch Umsetzung von Zuckern mit den Aminosäuren Lysin und/oder Arginin dargestellt werden.