5,7-dihydroxy-6-formyl-2-methylbenzopyran-4-one | 5186-27-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 5,7-dihydroxy-6-formyl-2-methylbenzopyran-4-one
• 英文别名: 6-formyl-5,7-dihydroxy-2-methylbenzopyran-4-one；5,7-dihydroxy-2-methyl-4-oxo-4H-chromene-6-carbaldehyde；5,7-Dihydroxy-2-methyl-4-oxo-4H-chromen-6-carbaldehyd；5,7-dihydroxy-2-methyl-4-oxochromene-6-carbaldehyde
• CAS: 5186-27-6
• 化学式: C₁₁H₈O₅
• 分子量: 220.182
• InChiKey: AGVYWJAGVXKCJF-UHFFFAOYSA-N

物化性质

• 熔点：
  198-200 °C
• 沸点：
  400.6±45.0 °C(Predicted)
• 密度：
  1.533±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,7-dihydroxy-6-formyl-2-methylbenzopyran-4-one 在 盐酸 、 amalgamated zinc 、 potassium carbonate 、 丙酮 作用下， 生成 甲基丁香色原酮
  参考文献：
  名称：

  Furo-chromones and -Coumarins. VII. Degradation of Visnagin, Khellin and Related Substances; Experiments with Chromic Acid and Hydrogen Peroxide; and a Synthesis of Eugenitin

  摘要：

  DOI：

  10.1021/ja01116a032
• 作为产物：
  描述：

  7-羟基-5-甲氧基-2-甲基-4-氧代-4H-1-苯并吡喃-6-甲醛 在 盐酸 、 水 作用下， 反应 1.0h， 生成 5,7-dihydroxy-6-formyl-2-methylbenzopyran-4-one
  参考文献：
  名称：

  Microplate assay for screening the antibacterial activity of Schiff bases derived from substituted benzopyran-4-one

  摘要：

  Schiff bases (SB1-SB3) were synthesized from the condensation of 6-formyl-7-hydroxy-5-methoxy2-methylbenzopyran-4-one with 2-aminopyridine (SB1), p-phenylenediamine (SB2) and o-phenylenediamine (SB3), while Schiff bases (SB4-SB6) were synthesized by condensation of 5,7-dihydroxy-6-formyl-2-methylbenzopyran-4-one with 2-aminopyridine (SB4), p-phenylenediamine (SB5) and o-phenylenediamine (SB6). Schiff bases were characterized using elemental analysis, IR, UV-Vis, H-1 NMR, C-13 NMR and mass spectroscopy. These compounds were screened for antibacterial activities by micro-plate assay technique. Escherichia coli and Staphylococcus capitis were exposed to different concentrations of the Schiff bases. Results showed that the antibacterial effect of these Schiff bases on Gram-negative bacteria were higher than that on Gram-positive bacteria moreover, the Schiff bases containing substituent OCH3 on position five have higher antibacterial activity than that containing hydroxy group on the same position, (C) 2012 Elsevier By. All rights reserved.

  DOI：

  10.1016/j.saa.2012.04.042

文献信息

• Murti et al., Proceedings - Indian Academy of Sciences, Section A, 1959, # 50, p. 192,194
  作者：Murti et al.

  DOI：——

  日期：——
• Chelation Behaviour of Ce(III), Th(IV), and UO2(VI) with 5,7-Dihydroxy-6-formyl-2-methylbenzopyran-4-one Schiff Bases
  作者：Yousry M. Issa、Omyma E. Sherif、Safaa M. Abbas

  DOI：10.1007/pl00010120

  日期：1998.10
• Antibacterial effect of some benzopyrone derivatives
  作者：Rehab Amin、Barbara Krammer、Nora Abdel-Kader、Thomas Verwanger、Aida El-Ansary

  DOI：10.1016/j.ejmech.2009.10.001

  日期：2010.1

  The Schiff base derivatives of benzopyran-4-one are characterized by imine groups which have biological activities such as antimicrobial, antifungal and antitumoral. The aim of this study was therefore to evaluate the toxicity of Schiff bases towards bacterial cells. Escherichia coli as Gram-negative bacteria and Staphylococcus capitis as Gram-positive bacteria were exposed to different concentrations of Schiff bases. For assessment of toxicity a 96-well turbidimetric procedure, capable of testing the antimicrobial properties on a single microplate. was used. Analysis of the growth curves showed that the antibacterial effect of these Schiff bases on Gram-negative bacteria was higher than that on Gram-positive. Furthermore the presence of hydroxylic groups is correlated with an increased antibacterial effect. (C) 2009 Elsevier Masson SAS. All rights reserved.
• Spectroscopic and biological activities studies of bivalent transition metal complexes of Schiff bases derived from condensation of 1,4-phenylenediamine and benzopyrone derivatives
  作者：Omaima E. Sherif、Nora S. Abdel-Kader

  DOI：10.1016/j.saa.2013.08.037

  日期：2014.1

  Many tools of analysis such as elemental analyses, infrared, ultraviolet-visible, electron spin resonance (ESR) and thermal analysis, as well as conductivity and magnetic susceptibility measurements were used to elucidate the structures of the newly prepared Co(II), Ni(II) and Cu(II) complexes with Schiff bases derived from the condensation of 1,4-phenylenediamine with 6-formyl-7-hydroxy-5-methoxy-2-methylbenzo-pyran-4-one (H2L) or 5,7-dihydroxy-6-formyl-2-methylbenzopyran-4-one (H4L). The data showed that all formed complexes are 1:1 or 2:2 (M:L) and non-electrolyte chelates. The Co(II) and Cu(II) complexes of the two Schiff bases were screened for antibacterial activities by the disk diffusion method. The antibacterial activity was screened using Escherichia coli and Staphylococcus capitis but the antifungal activity was examined by using Aspergillus flavus and Candida albicans. The Results showed that the tested complexes have antibacterial, except Cu-H4L, but not antifungal activities. (C) 2013 Elsevier B.V. All rights reserved.
• Microplate assay for screening the antibacterial activity of Schiff bases derived from substituted benzopyran-4-one
  作者：Rehab M. Amin、Nora S. Abdel-Kader、Aida L. El-Ansary

  DOI：10.1016/j.saa.2012.04.042

  日期：2012.9

  Schiff bases (SB1-SB3) were synthesized from the condensation of 6-formyl-7-hydroxy-5-methoxy2-methylbenzopyran-4-one with 2-aminopyridine (SB1), p-phenylenediamine (SB2) and o-phenylenediamine (SB3), while Schiff bases (SB4-SB6) were synthesized by condensation of 5,7-dihydroxy-6-formyl-2-methylbenzopyran-4-one with 2-aminopyridine (SB4), p-phenylenediamine (SB5) and o-phenylenediamine (SB6). Schiff bases were characterized using elemental analysis, IR, UV-Vis, H-1 NMR, C-13 NMR and mass spectroscopy. These compounds were screened for antibacterial activities by micro-plate assay technique. Escherichia coli and Staphylococcus capitis were exposed to different concentrations of the Schiff bases. Results showed that the antibacterial effect of these Schiff bases on Gram-negative bacteria were higher than that on Gram-positive bacteria moreover, the Schiff bases containing substituent OCH3 on position five have higher antibacterial activity than that containing hydroxy group on the same position, (C) 2012 Elsevier By. All rights reserved.