5-[(2-乙氧基苯基)氨基]-6-羟基-4(3H)-嘧啶酮 | 89595-66-4

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 中文名称: 5-[(2-乙氧基苯基)氨基]-6-羟基-4(3H)-嘧啶酮
• 中文别名: 9-[(1R)-5-甲基五呋喃糖基糖醛糖基]-9H-嘌呤-6-胺
• 英文名称: prunetin 5‐O‐glucoside
• 英文别名: prunetin 5-O-glucoside；prunetin 5-glucoside；prunetinoside；4H-1-Benzopyran-4-one, 5-(beta-D-glucopyranosyloxy)-3-(4-hydroxyphenyl)-7-methoxy-；3-(4-hydroxyphenyl)-7-methoxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• CAS: 89595-66-4
• 化学式: C₂₂H₂₂O₁₀
• 分子量: 446.411
• InChiKey: AJAGLPDYKVWJQE-RECXWPGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  155
• 氢给体数：
  5
• 氢受体数：
  10

制备方法与用途

生物活性

Prunetin 5-O-β-D-glucopyranoside 是从 Potentilla astracanica 提取物中分离得到的一种异黄酮，是一种有效的非竞争性 α-葡萄糖苷酶 (α-glucosidase) 抑制剂，其 IC50 值为 56.05 μg/mL。Prunetin 5-O-β-D-glucopyranoside 可用于 2 型糖尿病的研究。

靶点

IC50: 56.05 μg/mL (α-glucosidase)

反应信息

• 作为反应物：
  描述：

  5-[(2-乙氧基苯基)氨基]-6-羟基-4(3H)-嘧啶酮 在 盐酸 作用下， 以 水 为溶剂， 反应 0.75h， 生成 樱黄素
  参考文献：
  名称：

  Prunetin 5-O-β-d-glucopyranoside, an isoflavone from the peduncle of Prunus avium and P. Cerasus

  摘要：

  DOI：

  10.1016/s0031-9422(00)97795-1

文献信息

• Prunetin 5-O-β-d-glucopyranoside, an isoflavone from the peduncle of Prunus avium and P. Cerasus
  作者：S.A. Khalid、M. Gellért、K. Szendrei、Helmut Duddeck

  DOI：10.1016/s0031-9422(00)97795-1

  日期：——
• KHALID, S. A.;GELLERT, M.;SZENDREI, K.;DUDDECK, HELMUT, PHYTOCHEMISTRY, 28,(1989) N, C. 1560-1561
  作者：KHALID, S. A.、GELLERT, M.、SZENDREI, K.、DUDDECK, HELMUT

  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.