3-脱氧-2-戊酮糖 | 6815-38-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-脱氧-2-戊酮糖
• 英文名称: 3-deoxyxylosone
• 英文别名: 4,5-Dihydroxy-2-oxopentanal
• CAS: 6815-38-9
• 化学式: C₅H₈O₄
• 分子量: 132.116
• InChiKey: QFNWRVAZZYFNCF-UHFFFAOYSA-N

物化性质

• 沸点：
  316.5±32.0 °C(Predicted)
• 密度：
  1.309±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  糠醛 、 L-丙氨酸 、 3-脱氧-2-戊酮糖 在 phosphate buffer pH 7.0 作用下， 生成 (S)-4<(E)-1-formyl-2-(2-furyl)ethenyl>-5-(2-furyl)-2-<(2-furyl)methylidene>-2,3-dihydro-α-methyl-3-oxo-1H-pyrrole-1-acetic acid
  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
• 作为产物：
  描述：

  glutathion 在 sodium hydroxide 作用下， 以 水 为溶剂， 80.0~100.0 ℃ 、101.33 kPa 条件下， 反应 2.83h， 生成 3-脱氧-2-戊酮糖
  参考文献：
  名称：

  通过额外添加的谷胱甘肽或其组成氨基酸与热降解 N-(1-Deoxy-d-ribulos-1-yl)-谷胱甘肽副产物的相互作用促进吡嗪和含硫挥发性化合物的形成

  摘要：

  制备了源自核糖 (Rib) 和谷胱甘肽 (GSH) 的 Amadori 重排产物 (ARP)，并通过超高效液相色谱-串联质谱和核磁共振鉴定为N- (1- deoxy- d -ribulos-1-yl)-glutathione . 对ARP水溶液进行热处理，发现较高的温度会加速ARP的降解。120 ℃时生成的呋喃浓度是100 ℃时的6.39倍以上，特别是高温有利于糠醛和4-羟基-5-甲基-3(2 H)-呋喃酮通过脱氧松酮脱水。研究了额外添加的谷胱甘肽或其组成氨基酸在 ARP 热处理过程中挥发物形成中的促进作用。添加的 GSH 及其组成氨基酸都可以及时捕获乙二醛 (GO) 和甲基乙二醛 (MGO) 以促进 Strecker 降解，从而改善吡嗪的形成。与甘氨酸和谷氨酸相比，半胱氨酸是与GO和MGO反应生成吡嗪和甲基吡嗪最有效的外加氨基酸。更重要的是，额外添加的GSH降解的半胱氨酸通过半胱氨酸降解

  DOI：

  10.1021/acs.jafc.2c02949

文献信息

• [EN] TREATMENT OF SUGAR SOLUTIONS<br/>[FR] TRAITEMENT DE SOLUTIONS DE SUCRE
  申请人：WIVENHOE TECHNOLOGY LTD

  公开号：WO2005051968A1

  公开（公告）日：2005-06-09

  A process for treating a solution containing sugar and α-oxoaldehydes, comprising the step of adding a catalyst which comprises an optionally substituted histidine amino acid, such that the α-oxoaldehydes are catalytically converted to aldonic acids.

  处理含有糖和α-氧代醛的溶液的方法，包括添加一个催化剂，该催化剂包括一个可选择取代的组氨酸氨基酸，使α-氧代醛在催化作用下转化为醛酸。
• Maillard Browning Inhibition by Ellagic Acid via Its Adduct Formation with the Amadori Rearrangement Product
  作者：Heping Cui、Ziyan Wang、Mengyu Ma、Khizar Hayat、Qiang Zhang、Yan Xu、Xiaoming Zhang、Chi-Tang Ho

  DOI：10.1021/acs.jafc.1c03481

  日期：2021.9.1

  found effective for the inhibition of melanoidin formation in the xylose–glycine Maillard reaction but depended on its dosage and the point of time it was added in the reaction system. The lightest color of the Maillard reaction products was observed when ellagic acid was added at the 90th min, which was the point of time when the Amadori rearrangement product (ARP) developed the most. LC-ESI-MS/MS analysis

  应用逐步升温下的美拉德反应来研究鞣花酸对美拉德褐变的抑制作用。发现鞣花酸可有效抑制木糖-甘氨酸美拉德反应中的类黑素形成，但取决于其剂量和添加到反应系统中的时间点。当在第 90 分钟加入鞣花酸时，观察到美拉德反应产物的颜色最浅，这是 Amadori 重排产物 (ARP) 发展最多的时间点。LC-ESI-MS/MS 分析结果显示鞣花酸水解产物与主要中间体 ARP 反应生成加合物的趋势显着。加合物稳定了 ARP 并延迟了其分解并抑制了下游的褐变反应。
• Formation of Reactive Intermediates, Color, and Antioxidant Activity in the Maillard Reaction of Maltose in Comparison to <scp>d</scp>-Glucose
  作者：Clemens Kanzler、Helena Schestkowa、Paul T. Haase、Lothar W. Kroh

  DOI：10.1021/acs.jafc.7b04105

  日期：2017.10.11

  It was found, that the degradation of maltose predominantly yields 1,2-dicarbonyls that still carry a glucosyl moiety and thus subsequent reactions to HMF, furfural, and 2-acetylfuran are favored due to the elimination of d-glucose, which is an excellent leaving group in aqueous solution. Consequently, higher amounts of these heterocycles are formed from maltose. 3-deoxyglucosone and 3-deoxygalactosone

  在这项研究中，研究了麦芽糖和d-葡萄糖在1-丙氨酸存在下在130°C和pH 5下的美拉德反应。比较了两种碳水化合物的降解，褐变和抗氧化剂的反应性活动。为了确定反应途径中的相关差异，确定了所选中间体（如1,2-二羰基化合物，呋喃，呋喃酮和吡喃酮）的浓度。已发现，麦芽糖的降解主要产生仍带有葡糖基部分的1，2-二羰基，因此由于消除了d，因此有利于随后与HMF，糠醛和2-乙酰基呋喃的反应。-葡萄糖，它是水溶液中极好的离去基团。因此，由麦芽糖形成更高数量的这些杂环。3-脱氧葡糖酮和3-脱氧半乳糖酮是麦芽糖培养中唯一相关的C 6 -1,2-二羰基化合物，在加热的最初60分钟内以HMF形成的副产物形式以几乎等摩尔的量产生。
• Temperature-Dependent Catalysis of Glycylglycine on Its Amadori Compound Degradation to Deoxyosone
  作者：Heping Cui、Mengyu Ma、Ziyan Wang、Khizar Hayat、Xiaoming Zhang、Chi-Tang Ho

  DOI：10.1021/acs.jafc.2c03427

  日期：2022.7.13

  The Amadori rearrangement product derived from xylose–glycylglycine (XGG-ARP) is reactive to be attacked by another glycylglycine to generate a xylose–glycylglycine cross-linking product (XGG-CP) as a secondary product of the ARP. In this research, the role of additional glycylglycine in the XGG-ARP degradation was studied, and the dependence of glycylglycine on temperature was further clarified. The

  衍生自木糖-甘氨酰甘氨酸 (XGG-ARP) 的 Amadori 重排产物在被另一种甘氨酰甘氨酸攻击时具有反应性，可生成木糖-甘氨酰甘氨酸交联产物 (XGG-CP) 作为 ARP 的次级产物。本研究研究了额外的甘氨酰甘氨酸在XGG-ARP降解中的作用，进一步阐明了甘氨酰甘氨酸对温度的依赖性。XGG-CP 及其降解产物的产量受甘氨酰甘氨酸与 XGG-ARP 的摩尔比的显着影响。在反应物 XGG-ARP 和甘氨酰甘氨酸的相似总浓度下，随着甘氨酰甘氨酸与 XGG-ARP 摩尔比的增加，XGG-CP、3-脱氧木糖酮和糠醛的产率显着降低。然而，当反应温度升高到 120 °C 时，增加的额外甘氨酰甘氨酸百分比对 XGG-ARP 降解为脱氧松酮具有明显的催化作用，因此也提高了糠醛的收率。结果表明，增加的甘氨酰甘氨酸剂量水平增强了 XGG-ARP 向 XGG-CP 的转化和 XGG-CP 向 3-脱氧松酮
• Identification of Novel Colored Compounds Containing Pyrrole and Pyrrolinone Structures Formed by Maillard Reactions of Pentoses and Primary Amino Acids
  作者：Thomas Hofmann

  DOI：10.1021/jf980477i

  日期：1998.10.1

  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.