7-hydroxy-4-(3,4,5-trimethoxyphenyl)chromen-2-one | 858002-39-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 7-hydroxy-4-(3,4,5-trimethoxyphenyl)chromen-2-one
• 英文别名: 7-hydroxy-4-(3,4,5-trimethoxyphenyl)-3,4-dihydrocoumarin；7-hydroxy-4-(3,4,5-trimethoxy-phenyl)-coumarin；7-Hydroxy-4-(3,4,5-trimethoxy-phenyl)-cumarin；2H-1-Benzopyran-2-one, 7-hydroxy-4-(3,4,5-trimethoxyphenyl)-
• CAS: 858002-39-8
• 化学式: C₁₈H₁₆O₆
• mdl: MFCD31537595
• 分子量: 328.321
• InChiKey: HFNUTSAINFTYPQ-UHFFFAOYSA-N

物化性质

• 熔点：
  253 °C (decomp)(Solv: ethanol (64-17-5))
• 沸点：
  534.1±50.0 °C(Predicted)
• 密度：
  1.314±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 7-hydroxy-4-(3,4,5-trimethoxyphenyl)chromen-2-one 在 乙醚 作用下， 生成 7-methoxy-4-(3,4,5-trimethoxyphenyl)chromen-2-one
  参考文献：
  名称：

  Bargellini; Grippa, Gazzetta Chimica Italiana, 1927, vol. 57, p. 141

  摘要：

  DOI：
• 作为产物：
  描述：

  7-acetoxy-4-(3,4,5-trimethoxy-phenyl)-coumarin 在 硫酸 作用下， 生成 7-hydroxy-4-(3,4,5-trimethoxyphenyl)chromen-2-one
  参考文献：
  名称：

  Bargellini; Grippa, Gazzetta Chimica Italiana, 1927, vol. 57, p. 141

  摘要：

  DOI：

文献信息

• Antioxidant and antitumor activities of 4-arylcoumarins and 4-aryl-3,4-dihydrocoumarins
  作者：Keyun Zhang、Weixian Ding、Jie Sun、Bin Zhang、Fujiao Lu、Ren Lai、Yong Zou、Gabriel Yedid

  DOI：10.1016/j.biochi.2014.03.014

  日期：2014.12

  Five 4-arylcoumarins (1c-g) and twelve 3,4-dihydro-4-arylcoumarins (2a-l) were synthesized and tested for antioxidant activity, antitumor activity, toxicity and structure-activity relationships analysis. 4-Arylcoumarins and 3,4-dihydro-4-arylcoumarins that possess two hydroxyl groups in ortho position, such as 1d, 1f, 2a, 2f, 2g and 2h had stronger radical scavenging properties than that of vitamin C (Vit C) in ABTS(center dot+) assay. Kinetic traces of scavenging ABTS(center dot+) and DPPH radicals showed that all the reaction could reached endpoint in 1 min, which was similar with Vit C. 4-Arylcoumarins with 3'-hydroxyl-4'-methylphenyl structural show more efficient NO center dot radical scavenging activity. Three compounds 2e, 1f and 2a, in particular had superior EC50 for NO center dot scavenging than did Vit C. MTT assay indicated that one compound in particular had a potential antitumor effect, inhibiting proliferation of BGC-823 cells and almost completely killing them at a concentration 62.5 mg/L. With same concentration 100 mu g/mL, hemolytic analysis in rabbit red blood cells showed that only two compounds had hemolytic activity with a little more than 5% hemolysis. Injection and oral toxicity tests on Galleria mellonella larvae showed that none of the tested 4-arylcoumarins significantly affected their appetite, viability and mortality. (C) 2014 Elsevier B.V. and Societe francaise de biochimie et biologie Moleculaire (SFBBM). All rights reserved.
• Microwave-promoted automated synthesis of a coumarin library
  作者：M. Katkevičs、A. Kontijevskis、I. Mutule、E. Sūna

  DOI：10.1007/s10593-007-0025-x

  日期：2007.2
• Bogert; Isham, Journal of the American Chemical Society, 1914, vol. 36, p. 518
  作者：Bogert、Isham

  DOI：——

  日期：——