6-Hydroxy-2.4.3'-trimethoxy-4'-methoxymethoxy-benzylidenacetophenon | 111797-35-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 6-Hydroxy-2.4.3'-trimethoxy-4'-methoxymethoxy-benzylidenacetophenon
• CAS: 111797-35-4
• 化学式: C₂₀H₂₂O₇
• 分子量: 374.39
• InChiKey: JYCNNEJPPCNGSZ-UHFFFAOYSA-N

物化性质

• 沸点：
  576.7±50.0 °C(predicted)
• 密度：
  1.218±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

反应信息

• 作为反应物：
  描述：

  6-Hydroxy-2.4.3'-trimethoxy-4'-methoxymethoxy-benzylidenacetophenon 在 吡啶 、 碘 、 盐酸 作用下， 以 乙醇 、 水 、 异丙醇 为溶剂， 以25 %的产率得到4H-1-苯并吡喃-4-酮,2-(4-羟基-3-甲氧苯基)-5,7-二甲氧基-
  参考文献：
  名称：

  Antibacterial and Antioxidant Activity of Synthetic Polyoxygenated Flavonoids

  摘要：

  Flavonoids are an abundant class of naturally occurring compounds with broad biological activities, but their limited abundance in nature restricts their use in medicines and food additives. Here we present the synthesis and determination of the antibacterial and antioxidant activities of twenty-two structurally related flavonoids (five of which are new) by scientifically validated methods. Flavanones (FV1–FV11) had low inhibitory activity against the bacterial growth of MRSA 97-7. However, FV2 (C5,7,3′,4′ = OH) and FV6 (C5,7 = OH; C4′ = SCH3) had excellent bacterial growth inhibitory activity against Gram-negative E. coli (MIC = 25 µg/mL for both), while Chloramphenicol (MIC = 25 µg/mL) and FV1 (C5,7,3′ = OCH3; 4′ = OH) showed inhibitory activity against Gram-positive L. monocytogenes (MIC = 25 µg/mL). From the flavone series (FO1–FO11), FO2 (C5,7,3′,4′ = OH), FO3 (C5,7,4′ = OH; 3′ = OCH3), and FO5 (C5,7,4′ = OH) showed good inhibitory activity against Gram-positive MRSA 97-7 (MIC = 50, 12, and 50 µg/mL, respectively), with FO3 being more active than the positive control Vancomycin (MIC = 25 µg/mL). FO10 (C5,7= OH; 4′ = OCH3) showed high inhibitory activity against E. coli and L. monocytogenes (MIC = 25 and 15 µg/mL, respectively). These data add significantly to our knowledge of the structural requirements to combat these human pathogens. The positions and number of hydroxyl groups were key to the antibacterial and antioxidant activities.

  DOI：

  10.3390/ijms25115999
• 作为产物：
  描述：

  2-羟基-4,6-二甲氧基苯乙酮 、 3-甲氧基-4-(甲氧基甲氧基)苯甲醛 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 以75 %的产率得到6-Hydroxy-2.4.3'-trimethoxy-4'-methoxymethoxy-benzylidenacetophenon
  参考文献：
  名称：

  Antibacterial and Antioxidant Activity of Synthetic Polyoxygenated Flavonoids

  摘要：

  Flavonoids are an abundant class of naturally occurring compounds with broad biological activities, but their limited abundance in nature restricts their use in medicines and food additives. Here we present the synthesis and determination of the antibacterial and antioxidant activities of twenty-two structurally related flavonoids (five of which are new) by scientifically validated methods. Flavanones (FV1–FV11) had low inhibitory activity against the bacterial growth of MRSA 97-7. However, FV2 (C5,7,3′,4′ = OH) and FV6 (C5,7 = OH; C4′ = SCH3) had excellent bacterial growth inhibitory activity against Gram-negative E. coli (MIC = 25 µg/mL for both), while Chloramphenicol (MIC = 25 µg/mL) and FV1 (C5,7,3′ = OCH3; 4′ = OH) showed inhibitory activity against Gram-positive L. monocytogenes (MIC = 25 µg/mL). From the flavone series (FO1–FO11), FO2 (C5,7,3′,4′ = OH), FO3 (C5,7,4′ = OH; 3′ = OCH3), and FO5 (C5,7,4′ = OH) showed good inhibitory activity against Gram-positive MRSA 97-7 (MIC = 50, 12, and 50 µg/mL, respectively), with FO3 being more active than the positive control Vancomycin (MIC = 25 µg/mL). FO10 (C5,7= OH; 4′ = OCH3) showed high inhibitory activity against E. coli and L. monocytogenes (MIC = 25 and 15 µg/mL, respectively). These data add significantly to our knowledge of the structural requirements to combat these human pathogens. The positions and number of hydroxyl groups were key to the antibacterial and antioxidant activities.

  DOI：

  10.3390/ijms25115999