α-CEHC sulfate trimethylamine | 1088428-42-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: α-CEHC sulfate trimethylamine
• CAS: 1088428-42-5
• 化学式: C₃H₉N*C₁₆H₂₂O₇S
• 分子量: 417.524
• InChiKey: XCDRHSXMJMBWRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.92
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  113.37
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  α-CEHC sulfate trimethylamine 在 盐酸 、 水 、 异抗坏血酸 作用下， 反应 1.0h， 以82.5 μmol的产率得到3-(6-羟基-5,7,8-三甲基-3,4二氢苯并吡喃-2-基)丙酸甲酯
  参考文献：
  名称：

  Isolation and Identification of α-CEHC Sulfate in Rat Urine and an Improved Method for the Determination of Conjugated α-CEHC

  摘要：

  2,5,7,8-Tetramethyl-2-(2'-carboxyethyl)-6-hydroxychroman (alpha-CEHC), the water-soluble metabolite of alpha-tocopherol (alpha-TOH) with a shortened side chain but an intact hydroxychroman structure, has been identified in human urine and are thought to be produced in significant amount at excess intake of alpha-TOH. In previous studies, CEHCs in biological specimens were measured by HPLC, GC-MS or LC-MS, preceded by a hydrolysis procedure using either enzyme or methanolic HCI. In an attempt to analyze alpha-CEHC in rat urine accordingly, we observed that enzyme hydrolysis was relatively inefficient in releasing alpha-CEHC compared to high concentrations of HCI. The HCI releasable alpha-CEHC conjugate was isolated and chemically identified as 6-0-sulfated alpha-CEHC (alpha-CEHC sulfate). Using the synthetic alpha-CEHC sulfate standard, it was found that sulfatase could not hydrolyze to a significant extent. On the other hand, pretreatment with HCI at 60 degrees C in the presence of ascorbate, followed by a one-step ether extraction, not only hydrolyzed the sulfate conjugate completely but also extracted alpha-CEHC with high recovery. The inclusion of ascorbate minimized the conversion of alpha-CEHC to alpha-tocopheronolactone in the HCI pretreatment. A complete procedure for the quantitative analysis of alpha-CEHC including HCI hydrolysis, ether extraction and reverse phase isocratic HPLC-ECD was thus established. In conclusion, alpha-CEHC sulfate was isolated and identified as the HCI-releasable conjugate of alpha-CEHC in rat urine. A rapid and sensitive method with high reproducibility for the determination of free, conjugated and total alpha-CEHC is then established.

  DOI：

  10.1021/jf802459d