4,6-dimethoxy-2-hydroxyphenylacetic acid | 103323-54-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,6-dimethoxy-2-hydroxyphenylacetic acid
• 英文别名: (2-hydroxy-4,6-dimethoxy-phenyl)-acetic acid；(2-Hydroxy-4,6-dimethoxy-phenyl)-essigsaeure；2-(2-Hydroxy-4,6-dimethoxyphenyl)acetic acid；2-(2-hydroxy-4,6-dimethoxyphenyl)acetic acid
• CAS: 103323-54-2
• 化学式: C₁₀H₁₂O₅
• 分子量: 212.202
• InChiKey: LEWVFUGQBQMFGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,6-dimethoxy-2-hydroxyphenylacetic acid 生成 4,6-dimethoxybenzofuran-2(3H)-one
  参考文献：
  名称：

  Gripenberg; Juselius, Acta Chemica Scandinavica (1947), 1954, vol. 8, p. 734,737

  摘要：

  DOI：
• 作为产物：
  描述：

  3-Hydroxy-5,7-dimethoxy-cumarin 在 sodium hydroxide 作用下， 生成 4,6-dimethoxy-2-hydroxyphenylacetic acid
  参考文献：
  名称：

  Kubota et al., Nippon Kagaku Zasshi, 1956, vol. 77, p. 648

  摘要：

  DOI：

文献信息

• Gripenberg; Juselius, Acta Chemica Scandinavica (1947), 1954, vol. 8, p. 734,737
  作者：Gripenberg、Juselius

  DOI：——

  日期：——
• Functionalized aurones as inducers of NAD(P)H:quinone oxidoreductase 1 that activate AhR/XRE and Nrf2/ARE signaling pathways: Synthesis, evaluation and SAR
  作者：Chong-Yew Lee、Eng-Hui Chew、Mei-Lin Go

  DOI：10.1016/j.ejmech.2010.03.023

  日期：2010.7

  The chemopreventive potential of functionalized aurones and related compounds as inducers of NAD(P) H:quinone oxidoreductase 1 (NQO1, EC 1.6.99.2) are described. Several 4,6-dimethoxy and 5-hydroxyaurones induced NQO1 activity of Hepa1c1c7 cells by 2-fold at submicromolar concentrations, making these the most potent inducers to be identified from this class. Mechanistically, induction of NQO1 was mediated by the activation of AhR/XRE and Nrf2/ARE pathways, indicating that aurones may be mixed activators of NQO1 induction or agents capable of exploiting the proposed cross-talk between the AhR and Nrf2 gene batteries. QSAR analysis by partial least squares projection to latent structures (PLS) identified size parameters, in particular those associated with non-polar surface areas, as an important determinant of induction activity. These were largely determined by the substitution on rings A and B. A stereoelectronic role for the exocyclic double bond as reflected in the E-LUMO term was also identified. The electrophilicity of the double bond or its effect on the conformation of the target compound are possible key features for induction activity. (c) 2010 Elsevier Masson SAS. All rights reserved.
• Kubota et al., Nippon Kagaku Zasshi, 1956, vol. 77, p. 648
  作者：Kubota et al.

  DOI：——

  日期：——