(+/-)-2-hydroxy-3-(4-hydroxy-3,5-dinitro-phenyl)-propionic acid | 35772-94-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (+/-)-2-hydroxy-3-(4-hydroxy-3,5-dinitro-phenyl)-propionic acid
• 英文别名: (+/-)-2-Hydroxy-3-(4-hydroxy-3,5-dinitro-phenyl)-propionsaeure；3,5-Dinitro-4-hydroxyphenylmilchsaeure
• CAS: 35772-94-2
• 化学式: C₉H₈N₂O₈
• 分子量: 272.171
• InChiKey: COEGJOZSHFKGNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  164.04
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  DL-4-羟基苯乳酸 在 硝酸 作用下， 生成 (+/-)-2-hydroxy-3-(4-hydroxy-3,5-dinitro-phenyl)-propionic acid
  参考文献：
  名称：

  AM1 computational study on metabolites of 1,3-butadiene interstrand cross-linking DNA

  摘要：

  The alkylating reactions of 1,2-epoxy-3,4-butene (EB) and 1,2,3,4-diepoxybutane (DEB)-the important metabolites of rodent carcinogenic 1,3-butadiene, with adenine and cytosine and interaction with fragment of DNA on major groove-have been computed. Results show that there are little differences in activation energy between EB and DEB, so it is difficult to explain the fact that the mutagenicity of DEB is greater (about 100-fold) than that of EB by the ability of alkylation. It is also known that DEB can interstrand cross-link with DNA through two times alkylating reactions, whereas EB cannot. So this may contribute to the significant different genotoxicity of the two agents. Meanwhile, DEB can interstrand cross-link with many sequences of DNA in major groove vs. two in minor groove, which increases opportunity of interstrand cross-link with DNA in major groove. This difference may be the reason of base selection of DEB mutation. The deformation of some cross-linked DNA may also contribute to this selection to some degree.

  DOI：

  10.1007/bf02884674