p-nitrophenyl 7-dehydrochenodeoxycholate | 85359-00-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: p-nitrophenyl 7-dehydrochenodeoxycholate
• CAS: 85359-00-8
• 化学式: C₃₀H₄₁NO₆
• 分子量: 511.659
• InChiKey: GEHHGCHVXGEJER-VQIDHASQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.12
• 重原子数：
  37.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  106.74
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  p-nitrophenyl 7-dehydrochenodeoxycholate 在 无水碳酸镉 作用下， 以 吡啶 、 甲苯 为溶剂， 反应 7.0h， 生成 ethyl glyco-7-dehydrochenodeoxycholate 3-glucuronide acetate-methyl ester
  参考文献：
  名称：

  Studies on analysis of bile acids. Preparation of 3-glucuronides of 7- and 12-oxo bile acids.

  摘要：

  已合成具有7-或12-氧基团的未结合和糖结合、牛磺酸结合胆汁酸的3-葡萄糖醛酸酯。在C-3位引入葡萄糖醛酸残基是通过使用碳酸镉作为催化剂的Koenigs-Knorr反应实现的。结合胆汁酸的3-葡萄糖醛酸酯是通过三个串联反应制备的：与对硝基苯酚酯化、在C-3位进行葡萄糖醛酸化，以及与乙基甘氨酸或牛磺酸形成酰胺。简要讨论了氧基胆汁酸及相关化合物的3-葡萄糖醛酸酯的核磁共振光谱特性。

  DOI：

  10.1248/cpb.30.4422
• 作为产物：
  描述：

  对硝基苯酚 、 3Α-羟基-7-氧代-5Β-胆烷酸 在 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 乙酸乙酯 为溶剂， 以1.18 g的产率得到p-nitrophenyl 7-dehydrochenodeoxycholate
  参考文献：
  名称：

  Studies on analysis of bile acids. Preparation of 3-glucuronides of 7- and 12-oxo bile acids.

  摘要：

  已合成具有7-或12-氧基团的未结合和糖结合、牛磺酸结合胆汁酸的3-葡萄糖醛酸酯。在C-3位引入葡萄糖醛酸残基是通过使用碳酸镉作为催化剂的Koenigs-Knorr反应实现的。结合胆汁酸的3-葡萄糖醛酸酯是通过三个串联反应制备的：与对硝基苯酚酯化、在C-3位进行葡萄糖醛酸化，以及与乙基甘氨酸或牛磺酸形成酰胺。简要讨论了氧基胆汁酸及相关化合物的3-葡萄糖醛酸酯的核磁共振光谱特性。

  DOI：

  10.1248/cpb.30.4422

文献信息

• Identification of bile acid S-acyl glutathione conjugates in rat bile by liquid chromatography/electrospray ionization–linear ion trap mass spectrometry
  作者：Kuniko Mitamura、Naohiro Hori、Takashi Iida、Alan F. Hofmann、Shigeo Ikegawa

  DOI：10.1016/j.steroids.2010.09.002

  日期：2011.1

  Acyl-adenylates and acyl-CoA thioesters of bile acids (BAs) are reactive acyl-linked metabolites that have been shown to acylate the thiol group of glutathione (GSH); the reaction is catalyzed by glutathione S-transferase (GST) and the product is a thioester-linked BA-GSH conjugate. Such GSH conjugates are present in bile in lithocholic acid and ursodeoxycholic acid dosed-rats. To determine whether such novel BA-GSH conjugates are present in the bile of normal rats, we first synthesized the GSH conjugates of the major and minor biliary BAs of the rat and defined their MS and proton NMR properties. We then analyzed the BA-GSH composition in the bile of anesthetized biliary fistula rats by means of liquid chromatographic separation and electrospray ionization-linear ion trap mass spectrometric detection in negative- and positive-ion scan modes, monitoring characteristic transitions of the analytes. GSH conjugates of cholic, omega-muricholic, hyodeoxycholic, deoxycholic. 12-oxolithocholic, and lithocholic acids were present with concentrations in the range of 1.4-2.8 nmol/ml, some four orders of magnitude less than those of natural BA N-acyl amidates. Our results indicate that BA-GSH conjugates are formed and excreted in bile in the healthy rat, although this novel mode of BA conjugation is a very minor pathway. (C) 2010 Elsevier Inc. All rights reserved.