6-amino-4,5-bis-hydroxymethyl-2-methyl-pyridin-3-ol | 42242-40-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6-amino-4,5-bis-hydroxymethyl-2-methyl-pyridin-3-ol
• 英文别名: 6-Amino-4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol
• CAS: 42242-40-0
• 化学式: C₈H₁₂N₂O₃
• 分子量: 184.195
• InChiKey: AKDJPENCYUIIDX-UHFFFAOYSA-N

物化性质

• 沸点：
  572.5±50.0 °C(Predicted)
• 密度：
  1.447±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  99.6
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-amino-4,5-bis-hydroxymethyl-2-methyl-pyridin-3-ol 在 氢氟酸 、 sodium nitrite 作用下， 以 吡啶 为溶剂， 以50%的产率得到6-fluoropyridoxol
  参考文献：
  名称：

  Development of novel 19 F NMR pH indicators: synthesis and evaluation of a series of fluorinated vitamin B 6 analogues

  摘要：

  We have synthesized a series of novel fluorinated vitamin B-6 analogues (6-fluoropyridoxol derivatives) as potential F-19 NMR pH indicators for use in vivo. Modifications included addition of aldehyde, carboxyl or aminomethyl groups at the 4- or 5-ring position, and examination of a trifluoromethyl moiety as an internal chemical shift standard. The variation in chemical shift with respect to acid-base titration showed pK(a) values in the range 7.05-9.5 with a chemical shift sensitivity in the range 7.4-12 ppm. Several of the molecules readily cross cell membranes providing estimates of both intra- and extra-cellular pH in whole blood. 6-Fluoropyridoxamine (6-FPAM) exhibits a pK(a) = 7.05, which is closer to normal physiological pH than the parent molecule 6-fluoropyridoxol (6-FPOL) (pK(a) = 8.2), and should thus, be useful for precise and accurate measurements of pH in vivo. Enhanced spectral resolution for 6-FPAM over 6-FPOL is demonstrated in whole blood and the perfused rat heart. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00104-7

文献信息

• Development of novel 19 F NMR pH indicators: synthesis and evaluation of a series of fluorinated vitamin B 6 analogues
  作者：Sha He、Ralph P. Mason、Sandeep Hunjan、Vimal D. Mehta、Veera Arora、Revathi Katipally、Padmakar V. Kulkarni、Peter P. Antich

  DOI：10.1016/s0968-0896(98)00104-7

  日期：1998.9

  We have synthesized a series of novel fluorinated vitamin B-6 analogues (6-fluoropyridoxol derivatives) as potential F-19 NMR pH indicators for use in vivo. Modifications included addition of aldehyde, carboxyl or aminomethyl groups at the 4- or 5-ring position, and examination of a trifluoromethyl moiety as an internal chemical shift standard. The variation in chemical shift with respect to acid-base titration showed pK(a) values in the range 7.05-9.5 with a chemical shift sensitivity in the range 7.4-12 ppm. Several of the molecules readily cross cell membranes providing estimates of both intra- and extra-cellular pH in whole blood. 6-Fluoropyridoxamine (6-FPAM) exhibits a pK(a) = 7.05, which is closer to normal physiological pH than the parent molecule 6-fluoropyridoxol (6-FPOL) (pK(a) = 8.2), and should thus, be useful for precise and accurate measurements of pH in vivo. Enhanced spectral resolution for 6-FPAM over 6-FPOL is demonstrated in whole blood and the perfused rat heart. (C) 1998 Elsevier Science Ltd. All rights reserved.