1-[3-(α-D-glucopyranosyloxy)-2-furanyl]-1-ethanone | 85559-61-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[3-(α-D-glucopyranosyloxy)-2-furanyl]-1-ethanone
• 英文别名: 3-O-α-D-glucopyranosyloxy-2-furyl methyl ketone；3-O-α-D-glucopyranosyloxy-2-furylmethyl ketone；3-O-α-D-glucopyranosyloxy-furyl methyl ketone；isomaltol 3-O-α-D-glucopyranoside；glucosylisomaltol；3-O-a-D-Glucosyl Isomaltol；1-[3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyfuran-2-yl]ethanone
• CAS: 85559-61-1
• 化学式: C₁₂H₁₆O₈
• 分子量: 288.254
• InChiKey: RRYYNIJTMYUJDC-GPTQDWHKSA-N

物化性质

• 熔点：
  139-141°C
• 沸点：
  540.5±50.0 °C(Predicted)
• 密度：
  1.510±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（轻微）、甲醇（轻微、加热）

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  130
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-[3-(α-D-glucopyranosyloxy)-2-furanyl]-1-ethanone 在 四氢吡咯 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 1,6-脱水-β-D-葡萄糖
  参考文献：
  名称：

  Amine-catalyzed transformation of enolic nonenzymic browning products, isomaltol glycopyranosides into 1,6-anhydro-β-d-hexopyranoses

  摘要：

  DOI：

  10.1016/s0008-6215(00)90695-5
• 作为产物：
  描述：

  麦芽糖 在 盐酸 、 sodium hydroxide 、 sodium hydrogensulfite 、 溶剂黄146 作用下， 以 甲醇 、 乙二醇 为溶剂， 反应 8.5h， 生成 1-[3-(α-D-glucopyranosyloxy)-2-furanyl]-1-ethanone
  参考文献：
  名称：

  Characterization of a New Maillard Type Reaction Product Generated by Heating 1-Deoxymaltulosyl-glycine in the Presence of Cysteine

  摘要：

  The reaction between Amadori compounds and cysteine was investigated. When 1-deoxymaltulosyl-glycine (glycyl-fructosyl-glucose) was heated at 100 degrees C with cysteine in a neutral aqueous solution, a novel intermediate composed of 1-deoxyosone and cysteine was detected. NMR and mass spectrometry studies revealed the structure of the isolated intermediate to be 7,8a-dihydroxy-4a-methyl8-(alpha-D-glucopyranosyloxy)hexahydro-5-oxa-4-thia-1-azanaphthalene-2-carboxylic acid. This intermediate easily generated isomaltol and acetylfuran as volatile compounds in 1 mol/L HCl at 100 degrees C.

  DOI：

  10.1021/jf060296d

文献信息

• Novel substance having physiological activity, process for producing the same, and use
  申请人：——

  公开号：US20030045483A1

  公开（公告）日：2003-03-06

  A glucoside containing isomaltol represented by formula (I): 1 (wherein Sug represents a glucose residue or a sugar linkage composed of two or more glucose units) as an aglycon, a physiologically active substance containing the glucoside having human cytokine inducing ability increasing activity, a method for producing it, and food, medicine and feedstuff containing the substance.

  一种含有由式（I）：1 代表的异麦芽酮糖醇（其中 Sug 代表葡萄糖残基或由两个或两个以上的葡萄糖单元组成的糖连接体）作为苷元的葡糖苷，一种含有该葡糖苷的具有提高人类细胞因子诱导能力活性的生理活性物质，一种生产该物质的方法，以及含有该物质的食品、药品和饲料。
• Novel substance having physiological property, method for producing the same and uses thereof
  申请人：Fujii Hajime

  公开号：US20050143341A1

  公开（公告）日：2005-06-30

  A glucoside containing isomaltol represented by formula (I): (wherein Sug represents a glucose residue or a sugar linkage composed of two or more glucose units) as an aglycon, a physiologically active substance containing the glucoside having human cytokine inducing ability increasing activity, a method for producing it, and food, medicine and feedstuff containing the substance.

  一种含有由式(I)代表的异麦芽酮醇的葡糖苷： (其中 Sug 代表葡萄糖残基或由两个或两个以上葡萄糖单元组成的糖链）作为苷元的葡糖苷，含有该葡糖苷的具有提高人类细胞因子诱导能力活性的生理活性物质，其生产方法，以及含有该物质的食品、药品和饲料。
• Isolation of 3-O-α-d-gluco- and 3-O-β-d-galacto-pyranosyloxy-2-furyl methyl ketones from nonenzymic browning of maltose and lactose with secondary amino acids
  作者：James C. Goodwin

  DOI：10.1016/0008-6215(83)88160-9

  日期：1983.4
• Glucosylisomaltol, a New Indicator of Browning Reaction in Baby Cereals and Bread
  作者：Eduardo Guerra-Hernández、Antonio Ramirez-Jiménez、Belen García-Villanova

  DOI：10.1021/jf020461z

  日期：2002.12.1

  Glucosylisomaltol is proposed as a new indicator of the browning reaction in baby cereals and bread. The glucosylisomaltol was synthesized from maltose and proline, purified by semipreparative HPLC, and characterized by NMR, high-resolution mass spectrometry, and GG-MS analysis. Analysis of glucosylisomaltol, previously separated from cereals by centrifugation, was carried out by reversed-phase HPLC with UV detection in isocratic elution with water/acetonitrile (95:5). Mean recovery of glucosylisomaltol by the standard addition method was 96.9%. The relative standard deviation and detection limit were 1.56% and 0.14 mg/kg, respectively. This compound was identified in samples by the similarity of the t(R) and UV spectra to those of synthesized glucosylisomattol. Moreover, the glucosylisomattol from samples, previously separated by semipreparative HPLC, was acetylated and then separated and confirmed by GC-MS. Glucosylisomaltol was determined in baby cereals stored at 32 and 55 degreesC for 1 year and at 25 and 55 degreesC for I month at a water activity of 0.65. The amount of this indicator increased during storage from 0.48 to 7.7 mg/kg. The glucosylisomaltol was also determined in prebaked bread by heating at 190 degreesC for 30 min. The amount of this compound increased from nondetectable to 20.9 mg/kg after 30 min of baking. Glucosylisomaltol is a useful indicator to control the browning reaction during baby cereal storage and the baking of bread.
• NOVEL SUBSTANCE HAVING PHYSIOLOGICAL ACTIVITY, PROCESS FOR PRODUCING THE SAME, AND USE
  申请人：AMINO UP CHEMICAL CO. LTD.

  公开号：EP1298137B1

  公开（公告）日：2011-03-16