genistein 5-glucoside | 128508-06-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: genistein 5-glucoside
• 英文别名: genistein-5-O-β-D-glucopyranoside；7-hydroxy-3-(4-hydroxyphenyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• CAS: 128508-06-5
• 化学式: C₂₁H₂₀O₁₀
• 分子量: 432.384
• InChiKey: TXLQONQJSWSJJX-CMWLGVBASA-N

物化性质

• 沸点：
  814.2±65.0 °C(Predicted)
• 密度：
  1.642±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  166
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  genistein 5-glucoside 在 苹果酸 作用下， 生成 染料木素
  参考文献：
  名称：

  Flavonoid 5-glucosides from Prunus cerasus bark and their characteristic weak glycosidic bonding

  摘要：

  Pinostrobin 5-glucoside, a novel flavanone glycoside, was isolated from the bark of Prunus cerasus. As it was not found in P. avium, the substance is useful to distinguish these two species. Apigenin 5-glucoside genkwanin 5-glucoside and neosakuranin were also isolated from the bark of P. cerasus. They occur in both species as minor components. These 5-glucosides together with genistein 5-glucoside, prunetin 5-glucoside, sakuranin, tectochrysin 5-glucoside and luteolin 5-glucoside were hydrolysed in malic acid. The isoflavone and flavone 5-glucosides were shown to be hydrolysed more rapidly than the flavanone 5-glucosides, whereas no hydrolysis was observed with the corresponding 7-glucosides under the same conditions. The chalcone 2'-glucoside neosakuranin was transformed at first to the corresponding flavanone 5-glucoside, which was hydrolysed thereafter.

  DOI：

  10.1016/0031-9422(91)84200-c

文献信息

• GEIBEL, MARTIN;GEIGER, HANS;TREUTTER, DIETER, PHYTOCHEMISTRY, 29,(1990) N, C. 1351-1353
  作者：GEIBEL, MARTIN、GEIGER, HANS、TREUTTER, DIETER

  DOI：——

  日期：——
• Flavonoid 5-glucosides from Prunus cerasus bark and their characteristic weak glycosidic bonding
  作者：Martin Geibel、Walter Feucht

  DOI：10.1016/0031-9422(91)84200-c

  日期：1991.1

  Pinostrobin 5-glucoside, a novel flavanone glycoside, was isolated from the bark of Prunus cerasus. As it was not found in P. avium, the substance is useful to distinguish these two species. Apigenin 5-glucoside genkwanin 5-glucoside and neosakuranin were also isolated from the bark of P. cerasus. They occur in both species as minor components. These 5-glucosides together with genistein 5-glucoside, prunetin 5-glucoside, sakuranin, tectochrysin 5-glucoside and luteolin 5-glucoside were hydrolysed in malic acid. The isoflavone and flavone 5-glucosides were shown to be hydrolysed more rapidly than the flavanone 5-glucosides, whereas no hydrolysis was observed with the corresponding 7-glucosides under the same conditions. The chalcone 2'-glucoside neosakuranin was transformed at first to the corresponding flavanone 5-glucoside, which was hydrolysed thereafter.