2,4-O-dimethyl-β-orcinolcarboxylic acid | 56410-34-5

• 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: 2,4-O-dimethyl-β-orcinolcarboxylic acid
• 英文别名: 2,4-dimethoxy-3,6-dimethylbenzoic acid；2-O-methylrhizonic acid；2,4-Dimethoxy-3,6-dimethyl-benzoesaeure；Methylrhizoninsaeure；Rhizoninsaeure-methylaether
• CAS: 56410-34-5
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: AOIYPXVNUDBPRT-UHFFFAOYSA-N

物化性质

• 熔点：
  104.5 °C
• 沸点：
  332.1±37.0 °C(Predicted)
• 密度：
  1.151±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,4-O-dimethyl-β-orcinolcarboxylic acid 在 sodium hydroxide 、 正丁基锂 、 高氯酸 、 水 、 乙酸酐 、 三溴化硼 、 二异丙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 26.5h， 生成 6,8-dihydroxy-3,7-dimethylisocoumarin
  参考文献：
  名称：

  Lewis, Christopher N.; Staunton, James; Sunter, David C., Journal of the Chemical Society. Perkin transactions I, 1988, p. 747 - 754

  摘要：

  DOI：
• 作为产物：
  描述：

  2-羟基-4-甲氧基-6-甲基苯甲酸乙酯 在 palladium on activated charcoal 氢氧化钾 、 氢气 、 四氯化钛 、 potassium carbonate 、 溶剂黄146 作用下， 生成 2,4-O-dimethyl-β-orcinolcarboxylic acid
  参考文献：
  名称：

  Cresp,T.M. et al., Australian Journal of Chemistry, 1972, vol. 25, p. 2167 - 2184

  摘要：

  DOI：

文献信息

• Depsides as non-redox inhibitors of leukotriene B4 biosynthesis and HaCaT cell growth, 2. Novel analogues of obtusatic acid
  作者：S Kumar KC

  DOI：10.1016/s0223-5234(00)00132-x

  日期：2000.4

  acid analogues has been synthesized and evaluated as inhibitors of leukotriene B(4) (LTB(4)) biosynthesis and as antiproliferative agents. The 4-O-benzylated and the 4-O-demethylated congeners were the most potent inhibitors of LTB(4) production of the depside class of compounds, with IC(50) values in the submicromolar range. Furthermore, these compounds do not function as redox-based inhibitors because

  已合成了一系列的tus酸类似物，并被评估为白三烯B（4）（LTB（4））生物合成的抑制剂和抗增殖剂。4-O-苄基化和4-O-去甲基化同类物是最有效的Lpp（4）产生的深度类化合物的抑制剂，IC（50）值在亚微摩尔范围内。此外，这些化合物不能用作基于氧化还原的抑制剂，因为它们对稳定的自由基2,2,2-二苯基-1-吡啶并肼基不具有反应性，并且不产生可观量的脱氧核糖降解（作为衡量其生成潜力的量度）羟基自由基。一些钝化酸同源物也是角质形成细胞生长的有效抑制剂。生长抑制不是通过破坏细胞膜来介导的，
• Lichen acids, plant growth inhibitors from Usnea longissima
  作者：Yukiko Nishitoba、Iroyuki Nishimura、Tohru Nishiyama、Junya Mizutani

  DOI：10.1016/s0031-9422(00)82466-8

  日期：1987.1

  Abstract Eight components, depsides and orcinol derivatives which exhibit growth-inhibitory activity agai.

  摘要 八种成分，糖苷和地黄酚衍生物，它们再次表现出抑制生长的活性。
• Asahina; Hashimoto, Chemische Berichte, 1933, vol. 66, p. 641,645
  作者：Asahina、Hashimoto

  DOI：——

  日期：——
• Asahina; Fujikawa, Chemische Berichte, 1932, vol. 65, p. 580,582
  作者：Asahina、Fujikawa

  DOI：——

  日期：——
• Depsides as non-redox inhibitors of leukotriene B4 biosynthesis and HaCaT cell growth. 1. Novel analogues of barbatic and diffractaic acid
  作者：Sunil Kumar KC、Klaus Müller

  DOI：10.1016/s0223-5234(99)00132-4

  日期：1999.12

  A series of barbatic and diffractaic acid analogues has been synthesized and evaluated as inhibitors of leukotriene B-4 (LTB4) biosynthesis and as antiproliferative agents. The 4-O-demethyl barbatic and diffractaic acid derivatives were among the most active compounds in both assays. In particular, ethyl 4-O-demethylbarbatate was the most potent LTB4 biosynthesis inhibitor of this series, with an IC50 value in the submicromolar range. Because the compounds did not show appreciable reactivity against a stable free radical, 2,2-diphenyl-1-picrylhydrazyl, and did not produce appreciable amounts of deoxyribose degradation as a measure of their potency to generate hydroxyl radicals, a simple redox effect could not explain their biological activity. Also, there was no nonspecific cytotoxicity as documented by the activity of lactate dehydrogenase released from the cytoplasm of keratinocytes, which was in the control range. (C) 1999 Editions scientifiques et medicales Elsevier SAS.