P-苯甲基-β-D-葡萄糖酮酸 | 17680-99-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: P-苯甲基-β-D-葡萄糖酮酸
• 英文名称: p-cresol glucuronide
• 英文别名: 4-Methylphenol glucuronide；(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-methylphenoxy)oxane-2-carboxylic acid
• CAS: 17680-99-8
• 化学式: C₁₃H₁₆O₇
• 分子量: 284.266
• InChiKey: JPAUCQAJHLSMQW-XPORZQOISA-N

物化性质

• 熔点：
  138-141°C
• 沸点：
  549.7±50.0 °C(Predicted)
• 密度：
  1.524±0.06 g/cm3(Predicted)
• 溶解度：
  H2O：50 mg/mL，可溶
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 P-苯甲基-β-D-葡萄糖酮酸 、 乙酸酐 在 吡啶 、 甲醇 、 乙醚 作用下， 生成 4-(methyl)phenyl-beta-D-glucopyranosiduronic acid methyl ester tetraacetate
  参考文献：
  名称：

  Kamil et al., Biochemical Journal, 1951, vol. 50, p. 235,236

  摘要：

  DOI：
• 作为产物：
  描述：

  4-(methyl)phenyl-beta-D-glucopyranosiduronic acid methyl ester tetraacetate 在 甲醇 、 barium dihydroxide 、 水 、 sodium methylate 作用下， 生成 P-苯甲基-β-D-葡萄糖酮酸
  参考文献：
  名称：

  Helferich; Berger, Chemische Berichte, 1957, vol. 90, p. 2492,2495

  摘要：

  DOI：

文献信息

• Determination of Kow Values for a Series of Aryl Glucuronides
  作者：D. W. Kuehl、J. Christensen

  DOI：10.1007/s001289900955

  日期：1999.7.1
• Urinary metabolomics in Fxr-null mice reveals activated adaptive metabolic pathways upon bile acid challenge
  作者：Joo-Youn Cho、Tsutomu Matsubara、Dong Wook Kang、Sung-Hoon Ahn、Kristopher W. Krausz、Jeffrey R. Idle、Hans Luecke、Frank J. Gonzalez

  DOI：10.1194/jlr.m002923

  日期：2010.5

  Farnesoid X receptor (FXR) is a nuclear receptor that regulates genes involved in synthesis, metabolism, and transport of bile acids and thus plays a major role in maintaining bile acid homeostasis. In this study, metabolomic responses were investigated in urine of wild-type and Fxr-null mice fed cholic acid, an FXR ligand, using ultra-performance liquid chromatography (UPLC) coupled with electrospray time-of-flight mass spectrometry (TOFMS). Multivariate data analysis between wild-type and Fxr-null mice on a cholic acid diet revealed that the most increased ions were metabolites of p-cresol (4-methylphenol), corticosterone, and cholic acid in Fxr-null mice. The structural identities of the above metabolites were confirmed by chemical synthesis and by comparing retention time (RT) and/or tandem mass fragmentation patterns of the urinary metabolites with the authentic standards. Tauro-3 alpha,6,7 alpha,12 alpha-tetrol (3 alpha,6,7 alpha,12 alpha-tetrahydroxy-5 beta-cholestan-26-oyltaurine), one of the most increased metabolites in Fxr-null mice on a CA diet, is a marker for efficient hydroxylation of toxic bile acids possibly through induction of Cyp3a11. A cholestatic model induced by lithocholic acid revealed that enhanced expression of Cyp3a11 is the major defense mechanism to detoxify cholestatic bile acids in Fxr-null mice. These results will be useful for identification of biomarkers for cholestasis and for determination of adaptive molecular mechanisms in cholestasis.-Cho, J. Y., T. Matsubara, D. W. Kang, S. H. Ahn, K. W. Krausz, J. R. Idle, H. Luecke, and F. J. Gonzalez. Urinary metabolomics in Fxr-null mice reveals activated adaptive metabolic pathways upon bile acid challenge. J. Lipid Res. 2010. 51: 1063-1074.