4-formyl-2-methoxyphenyl neopentyl sulfate | 1301740-24-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机硫酸及其衍生物
• 英文名称: 4-formyl-2-methoxyphenyl neopentyl sulfate
• CAS: 1301740-24-8
• 化学式: C₁₃H₁₈O₆S
• 分子量: 302.348
• InChiKey: FFLWBISFUBAWRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.19
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  78.9
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (1S,3R,4R,5R)-3-(2-carboxyacetyl)oxy-1,4,5-trihydroxycyclohexane-1-carboxylic acid 、 4-formyl-2-methoxyphenyl neopentyl sulfate 在 哌啶 、 4-二甲氨基吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 168.0h， 以550 mg的产率得到
  参考文献：
  名称：

  First Chemical Synthesis and in Vitro Characterization of the Potential Human Metabolites 5-O-Feruloylquinic Acid 4′-Sulfate and 4′-O-Glucuronide

  摘要：

  Feruloylquinic acids are a major class of biologically active phenolic antioxidants in coffee beans, but their metabolic fate is poorly understood. The present study investigated the phase II metabolism of feruloylquinic adds with selected human sulfotransferases (SULT1A1 and SULT1E1) and uridine 5'-diphosphoglucuronosyltransferases (UGT1A1 and UGT1A9). For unequivocal metabolite identification, the chemical synthesis of two potential human metabolites of 5-O-feruloylquinic acid, the 4'-sulfated and 4'-O-glucuronidated conjugates, has been performed for the first time. Following incubation with human SULT1A1 or SULT1E1, formation of 5-O-feruloylquinic acid 4'-O-sulfate was confirmed by matching its HPLC and MS data with those of the authentic standard. On the other hand, no glucuronide conjugates were detected after incubation with human uridine 5'-diphosphoglucuronosyltransferases. These results suggest that sulfation can take place on the ferulic acid moiety of feruloylquinic acids and may be a major metabolic pathway for feruloylquinic acids in humans.

  DOI：

  10.1021/jf200272m
• 作为产物：
  描述：

  2,2-二甲基丙烷-1-磺酰氯 、 香草醛 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.17h， 以71%的产率得到4-formyl-2-methoxyphenyl neopentyl sulfate
  参考文献：
  名称：

  First Chemical Synthesis and in Vitro Characterization of the Potential Human Metabolites 5-O-Feruloylquinic Acid 4′-Sulfate and 4′-O-Glucuronide

  摘要：

  Feruloylquinic acids are a major class of biologically active phenolic antioxidants in coffee beans, but their metabolic fate is poorly understood. The present study investigated the phase II metabolism of feruloylquinic adds with selected human sulfotransferases (SULT1A1 and SULT1E1) and uridine 5'-diphosphoglucuronosyltransferases (UGT1A1 and UGT1A9). For unequivocal metabolite identification, the chemical synthesis of two potential human metabolites of 5-O-feruloylquinic acid, the 4'-sulfated and 4'-O-glucuronidated conjugates, has been performed for the first time. Following incubation with human SULT1A1 or SULT1E1, formation of 5-O-feruloylquinic acid 4'-O-sulfate was confirmed by matching its HPLC and MS data with those of the authentic standard. On the other hand, no glucuronide conjugates were detected after incubation with human uridine 5'-diphosphoglucuronosyltransferases. These results suggest that sulfation can take place on the ferulic acid moiety of feruloylquinic acids and may be a major metabolic pathway for feruloylquinic acids in humans.

  DOI：

  10.1021/jf200272m