(2S,3S,4S,5R,6S)-6-{3,5-Dihydroxy-4-[(E)-3-(4-hydroxy-phenyl)-acryloyl]-phenoxy}-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid | 929051-24-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: (2S,3S,4S,5R,6S)-6-{3,5-Dihydroxy-4-[(E)-3-(4-hydroxy-phenyl)-acryloyl]-phenoxy}-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid
• CAS: 929051-24-1
• 化学式: C₂₁H₂₀O₁₁
• 分子量: 448.383
• InChiKey: IYVGSPYAOAONMC-KAHJDZKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.03
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  194.21
• 氢给体数：
  7.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,5R,6S)-6-{3,5-Dihydroxy-4-[(E)-3-(4-hydroxy-phenyl)-acryloyl]-phenoxy}-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 66.0h， 以49 mg的产率得到naringenin 7-O-β-D-glucuronide sodium salt
  参考文献：
  名称：

  Identification of isomeric flavonoid glucuronides in urine and plasma by metal complexation and LC-ESI-MS/MS

  摘要：

  AbstractNoncovalent complexes were used for structural determination and isomer differentiation of flavonoid glucuronides. Several flavonoid glucuronides including naringenin‐7‐O‐glucuronide, synthesized here for the first time, were used as test compounds. Electrospray ionization quadrupole ion trap mass spectrometry with collision‐induced dissociation (CID) was used to analyze complexes of the form [Co(II) (L‐H) (Aux)]+ and [Co(II) (L‐H) (Aux)2]+, in which L is the flavonoid glucuronide and Aux is a phenanthroline‐based ligand. These complexes yielded characteristic fragmentation patterns that facilitated assignment of the substitution position of the glucuronides. The methods were adapted to liquid chromatography/tandem mass spectrometry (LC‐MS/MS) with postcolumn cobalt complexation and were tested on extracts from biological fluids. The metabolites naringenin‐7‐O‐glucuronide and naringenin‐4′‐O‐glucuronide were detected in human urine following the consumption of grapefruit juice. Isomeric quercetin glucuronides were identified and differentiated after spiking rat plasma at the 1 µM level, proving that the new methods are effective at biologically relevant concentrations. Copyright © 2006 John Wiley & Sons, Ltd.

  DOI：

  10.1002/jms.1050
• 作为产物：
  描述：

  2-(4-acetoxyphenyl)-5-hydroxy-4-oxochroman-7-yl acetate 在 吡啶 、 4 A molecular sieve 、 咪唑盐酸盐 、 sodium carbonate 、 silver(l) oxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 21.0h， 生成 (2S,3S,4S,5R,6S)-6-{3,5-Dihydroxy-4-[(E)-3-(4-hydroxy-phenyl)-acryloyl]-phenoxy}-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid
  参考文献：
  名称：

  Identification of isomeric flavonoid glucuronides in urine and plasma by metal complexation and LC-ESI-MS/MS

  摘要：

  AbstractNoncovalent complexes were used for structural determination and isomer differentiation of flavonoid glucuronides. Several flavonoid glucuronides including naringenin‐7‐O‐glucuronide, synthesized here for the first time, were used as test compounds. Electrospray ionization quadrupole ion trap mass spectrometry with collision‐induced dissociation (CID) was used to analyze complexes of the form [Co(II) (L‐H) (Aux)]+ and [Co(II) (L‐H) (Aux)2]+, in which L is the flavonoid glucuronide and Aux is a phenanthroline‐based ligand. These complexes yielded characteristic fragmentation patterns that facilitated assignment of the substitution position of the glucuronides. The methods were adapted to liquid chromatography/tandem mass spectrometry (LC‐MS/MS) with postcolumn cobalt complexation and were tested on extracts from biological fluids. The metabolites naringenin‐7‐O‐glucuronide and naringenin‐4′‐O‐glucuronide were detected in human urine following the consumption of grapefruit juice. Isomeric quercetin glucuronides were identified and differentiated after spiking rat plasma at the 1 µM level, proving that the new methods are effective at biologically relevant concentrations. Copyright © 2006 John Wiley & Sons, Ltd.

  DOI：

  10.1002/jms.1050