4-hydroxy-2-(hydroxymethyl)-5-methyl-3(2H)-furanone | 17678-20-5

• 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-(hydroxymethyl)-5-methyl-3(2H)-furanone
• 英文别名: 4-hydroxy-2-(hydroxymethyl)-5-methylfuran-3(2H)-one；4-hydroxy-2-hydroxymethyl-5-methyl-3(2H)-furanone；4-Hydroxy-2-hydroxymethyl-5-methyl-2H-furan-3-on；4-hydroxy-2-(hydroxymethyl)-5-methylfuran-3-one
• CAS: 17678-20-5
• 化学式: C₆H₈O₄
• 分子量: 144.127
• InChiKey: QWWDOOYYVCSCLB-UHFFFAOYSA-N

物化性质

• 沸点：
  303.2±42.0 °C(Predicted)
• 密度：
  1.425±0.06 g/cm3(Predicted)
• LogP：
  -0.635 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  葡萄糖 在 聚甘氨酸 作用下， 以 水 为溶剂， 反应 4.0h， 以7.1 mg的产率得到2,3-二氢-3,5-二羟基-6-甲基-4H-吡喃-4-酮
  参考文献：
  名称：

  DNA strand-breaking activity and mutagenicity of 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one (DDMP), a Maillard reaction product of glucose and glycine

  摘要：

  Aqueous solution of glucose and glycine was heated under reflux for 4 h and extracted with ethyl acetate. Reversed phase HPLC of the extract revealed a new DNA strand-breaking substance, which was purified by repeated HPLC and identified as 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one (DDMP). DDMP induced DNA strand breaking in a dose-and time-dependent manner. It was active to break DNA strands at pH 7.4 and 9.4. Its pyranone skeleton was destroyed at the pH values. DNA strand breaking by DDMP was inhibited by superoxide dismutase, catalase, scavengers for hydroxyl radical, spin trapping agents and metal chelators, and the breaking was enhanced by Fe(III) ion. A mixture of DDMP and a spin trap DMPO gave electron spin resonance signals of a spin adduct DMPO-OH, indicating generation of hydroxyl radical. DDMP was found to be mutagenic to Salmonella typhimurium TA100 without metabolic activation. These results show DDMP generated active oxygen species to cause DNA strand breaking and mutagenesis. (C) 1997 Elsevier Science B.V.

  DOI：

  10.1016/s1383-5718(97)00141-1

文献信息

• Synthesis of a derivative of 1-deoxy-d-erythro-2,3-hexodiulose and its conversion into nonenzymic browning products
  作者：Benjamin E. Fisher、Henry B. Sinclair、James C. Goodwin

  DOI：10.1016/0008-6215(83)88110-5

  日期：1983.6

  hydrolysis of 5 produced 6 , which without isolation was treated with piperidine acetate to yield piperidino-hexose-reductone ( 7 ) and 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one ( 8 ). A third component in the reaction mixture has been tentatively assigned from mass-spectroscopic data the structure 4-hydroxy-2-hydroxymethyl-5-methyl-3(2 H )-furanone ( 9 ).

  摘要一种新型的1-脱氧-4,5-O-异亚丙基-d-赤藓-2,3-己二糖（5）的合成方法，是一种难以捉摸的1-脱氧-赤藓-2,3-己二糖的稳定衍生物（在图6中，描述了从3，6-脱水-4，5-O-异亚丙基-d-甘露糖醇（1）开始。5的酸水解产生6，将其未经分离地用乙酸哌啶处理，得到哌啶子基-己糖-还原酮（7）和2,3-二氢-3,5-二羟基-6-甲基-4H-吡喃-4-酮（7） 8）。已从质谱数据中初步确定了反应混合物中的第三种成分为结构4-羟基-2-羟基甲基-5-甲基-3（2 H）-呋喃酮（9）。
• Analysis of Furanone, Pyranone, and New Heterocyclic Colored Compounds from Sugar−Glycine Model Maillard Systems
  作者：Jennifer M. Ames、Richard G. Bailey、John Mann

  DOI：10.1021/jf980528b

  日期：1999.2.1

  experiments, as the related compounds 4-hydroxy-2-(hydroxymethyl)-5-methyl-3(2H)-furanone and 2, 3-dihydro-3,5-dihydroxy-6-methyl-4H-pyranone. The remaining compound from the glucose system and the colorless compound from the xylose system were identified as 5-(hydroxymethyl)furfural and 4-hydroxy-5-methyl-3(2H)-furanone, respectively.

  将含水糖（木糖或葡萄糖）-甘氨酸模型系统回流2小时，pH保持在5。总反应产物的反相HPLC给出了木糖系统的两个已分离峰（其中一个是有色的），五个已分离的峰葡萄糖系统的峰（其中两个是有色的）。通过半制备HPLC从乙酸乙酯提取物中分离出负责这些峰的组分。主要使用NMR，将木糖系统中的有色化合物鉴定为新的2-乙酰基-6-（羟甲基）-5,6-二氢-4H-吡啶酮。来自葡萄糖系统的有色化合物最有可能是相关新化合物2-乙酰基-6-羟基-7-（羟甲基）-1,5,6,7-四氢-4H-的两个新的顺式/反式环异构体azepinone + ++。这些化合物是从糖-氨基酸模型系统中分离出来的第一个单环结构，据报道是有色的。主要通过NMR实验确定了葡萄糖系统中的两个无色成分，分别为相关化合物4-羟基-2-（羟甲基）-5-甲基-3（2H）-呋喃酮和2，3-二氢-3， 5-二羟基-6-甲基-4H-吡喃酮。来自葡萄糖系统的
• Reactivity of 1-Deoxy-<scp>d</scp>-<i>erythro</i>-hexo-2,3-diulose: A Key Intermediate in the Maillard Chemistry of Hexoses
  作者：Michael Voigt、Marcus A. Glomb

  DOI：10.1021/jf900459x

  日期：2009.6.10

  Among the compounds identified were carboxylic acids (glyceric acid and acetic acid) that can be seen as stable Maillard end-products. However, the formation of dicarbonyls (3,4-dihydroxy-2-oxobutanal, 1-hydroxybutane-2,3-dione, and 4-hydroxy-2-oxobutanal) and of hydroxycarbonyls (acetol) was verified presenting unstable, reactive Maillard intermediates. Results confirmed that β-dicarbonyl cleavage

  在1-丙氨酸存在下，在中等条件下（37和50°C）研究了1-脱氧己基-2,3-二糖（美拉德化学中的关键中间体）的降解。完成了各种分析策略，以涵盖所形成产物的广泛范围及其不同的化学性质。这些涉及GC-MS分析三甲基甲硅烷和ö -benzyloxime三甲基甲硅烷衍生物（与反应后ö -benzylhydroxylamine和Ñ，ö，GC-FID（后乙酸癸基酯的分析用氯甲酸癸基反应-双（三甲基硅烷基）乙酰胺） ）和喹喔啉衍生物的HPLC-UV分析（与邻苯二酚反应后-苯二胺）。在鉴定出的化合物中，有羧酸（甘油酸和乙酸），可以认为是稳定的美拉德终产物。但是，已证实形成了二羰基（3,4-二羟基-2-氧杂双醛，1-羟基丁烷-2,3-二酮和4-羟基-2-氧杂双醛）和羟基羰基（丙酮醇），表明存在不稳定的反应性美拉德中间体。结果证实，β-二羰基裂解是1-deoxyhexo-2,3-diulose降解中非常重要
• Oxygen-Dependent Fragmentation Reactions during the Degradation of 1-Deoxy-<scp>d</scp>-<i>erythro</i>-hexo-2,3-diulose
  作者：Michael Voigt、Mareen Smuda、Christoph Pfahler、Marcus A. Glomb

  DOI：10.1021/jf100140h

  日期：2010.5.12

  With this work, we report on further insights into the chemistry of 1-deoxy-o-erythro-hexo-2,3-diulose (1-deoxyglucosone, 1-DG). This alpha-dicarbonyl plays an important role as a highly reactive intermediate in the Maillard chemistry of hexoses. Degradation of 1-DG in the presence of the amino acid L-alanine led to the formation of several products. Lactic acid and glyceric acid were found to be major degradation products. Their formation was dependent on the presence of oxygen. Therefore, a mechanism is postulated based on oxidation leading to a tricarbonyl intermediate. Carbonyl cleavage of this structure should then give rise to carboxylic acids. This mechanism was supported by the isotope distribution observed during degradation of different (13)C-labeled D-glucose isotopomers. Furthermore, we identified 3,5-dihydroxy-6-methyl-2,3-dihydro-4H-pyran-4-one (gamma-pyranone) to be capable of rehydration forming 1-DG to a minor extent and therefore leading to the same degradation products. The formation of carboxylic acids from gamma-pyranone was also dependent on the presence of oxygen in agreement with the postulated oxidative fragmentation. Finally, we investigated the formation of aldehydes expected as retro-aldol products formed within the degradation of 1-DG. Results seemed to rule out this reaction as an important degradation pathway under the conditions investigated herein.
• POLYMER IMMOBILIZED LIVING CELLS AND APPLICATIONS THEREOF
  申请人：HOLLAND BIOMATERIALS GROUP B.V.

  公开号：EP1113827A1

  公开（公告）日：2001-07-11