黄尿酸8-O-葡糖苷 | 97451-32-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 黄尿酸8-O-葡糖苷
• 中文别名: (3β,17xi)-22-氨基胆甾-5-烯-3-醇
• 英文名称: xanthurenic acid 8-O-beta-D-glucoside
• 英文别名: xanthurenic acid 8-O-β-D-glucoside；Xanthurenic acid 8-O-glucoside；4-oxo-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1H-quinoline-2-carboxylic acid
• CAS: 97451-32-6
• 化学式: C₁₆H₁₇NO₉
• 分子量: 367.312
• InChiKey: MYFHOUJDPFBJLH-RSQMQNDGSA-N

物化性质

• 沸点：
  730.4±60.0 °C(Predicted)
• 密度：
  1.709±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  166
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  xanthurenic acid 2,3,4,6-tetra-O-acetyl 8-β-D-glucoside 在 甲醇 、 sodium methylate 、 盐酸 作用下， 以 水 为溶剂， 反应 1.0h， 以82%的产率得到黄尿酸8-O-葡糖苷
  参考文献：
  名称：

  Xanthurenic acid derivative pharmaceutical compositions and methods related thereto

  摘要：

  本发明涉及利尿药物组合物和方法，特别是涉及公式I的某些衍生物：或其前药或药学上可接受的盐；以及药学上可接受的载体。

  公开号：

  US20060217322A1

文献信息

• REAL, M. DOLORES;FERRE, JUAN, J. BIOL. CHEM., 265,(1990) N3, C. 7407-7412
  作者：REAL, M. DOLORES、FERRE, JUAN

  DOI：——

  日期：——
• Role of Xanthurenic Acid 8-O-β-d-Glucoside, a Novel Fluorophore that Accumulates in the Brunescent Human Eye Lens¶
  作者：Geetha Thiagarajan、Etsuko Shirao、Kanako Ando、Amane Inoue、Dorairajan Balasubramanian

  DOI：10.1562/0031-8655(2002)076<0368:roxaod>2.0.co;2

  日期：——

  We have been able to identify a blue fluorophore from the low-molecular weight soluble fraction of human adult nondiabetic brunescent cataract lenses As xanthurenic acid 8-O-beta-D-glucoside (XA8OG) (excitation 338 nm and emission = 440 nm). To determine the role of this fluorophore in the lens, we have examined its photophysical and photodynamic properties. We found XA80G to have a fluorescence quantum yield (phi) of 0.22 and a major emission lifetime of 12 us. We found it to be a UVA-region sensitizer, capable of efficiently generating singlet oxygen species hut little of superoxide We also demonstrated that XA80G oxidizes proteins when irradiated with UVA light, causing photodynamic covalent chemical damage to proteins. Its Accumulation in the aging human lens (and the attendant decrease of its precursor O-beta-D-glucoside of 3-hydroxykynurenine) can, thus, add to the oxidative burden on the system. XA80G, thus, appears to be an endogenous chromophore in the lens, which can act as a cataractogenic agent.