5,7,3',4'-tetrahydroxy-5'-methoxyflavone, | 60303-28-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 5,7,3',4'-tetrahydroxy-5'-methoxyflavone,
• 英文别名: tricetine-3'-methyl ether；tricetin 3'-methyl ether；selagin；selgin；3'-O-methyltricetin；2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxychromen-4-one
• CAS: 60303-28-8
• 化学式: C₁₆H₁₂O₇
• 分子量: 316.267
• InChiKey: UGPOBASOHYMNAK-UHFFFAOYSA-N

物化性质

• 熔点：
  353-354 °C
• 沸点：
  642.5±55.0 °C(Predicted)
• 密度：
  1.605±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  反式-3-(4-羟基-3-甲氧基苯基)-2-丙烯-1-醇 、 5,7,3',4'-tetrahydroxy-5'-methoxyflavone, 在 silver carbonate 作用下， 以 丙酮 、 苯 为溶剂， 反应 7.0h， 以33%的产率得到(+/-)-5'-methoxyhydnocarpin-D
  参考文献：
  名称：

  Synthesis and Structures of Regioisomeric Hydnocarpin-Type Flavonolignans

  摘要：

  Flavonolignans represent natural compounds whose biosynthesis presumes a radical coupling of a ring B catecholic flavonoid with a molecule of coniferyl alcohol or an analogue. Many natural flavonolignans can exist as regioisomers, depending on how the coupled coniferyl alcohol moiety orients to the flavonoid. These regioisomers are often difficult to separate and have virtually identical NMR spectra. Structural assignments for some have changed with time or have been given without proof. We here report syntheses of both regioisomers of the flavonolignan hydnocarpin and one isomer of a plant isolate previously known as 5'-methoxyhydnocarpin. This isomer, here renamed 5'-methoxyhydnocarpin-D, was recently shown to be a potent inhibitor of a Staphylococcus aureus multidrug resistant efflux pump.

  DOI：

  10.1021/np000166d
• 作为产物：
  描述：

  1-[2-羟基-4,6-双(甲氧基甲氧基)苯基]乙酮,2',4'-双(甲氧基甲氧基)-6'-羟基苯乙酮 在 盐酸 、 氢氧化钾 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 为溶剂， 反应 65.33h， 生成 5,7,3',4'-tetrahydroxy-5'-methoxyflavone,
  参考文献：
  名称：

  Synthesis and Structures of Regioisomeric Hydnocarpin-Type Flavonolignans

  摘要：

  Flavonolignans represent natural compounds whose biosynthesis presumes a radical coupling of a ring B catecholic flavonoid with a molecule of coniferyl alcohol or an analogue. Many natural flavonolignans can exist as regioisomers, depending on how the coupled coniferyl alcohol moiety orients to the flavonoid. These regioisomers are often difficult to separate and have virtually identical NMR spectra. Structural assignments for some have changed with time or have been given without proof. We here report syntheses of both regioisomers of the flavonolignan hydnocarpin and one isomer of a plant isolate previously known as 5'-methoxyhydnocarpin. This isomer, here renamed 5'-methoxyhydnocarpin-D, was recently shown to be a potent inhibitor of a Staphylococcus aureus multidrug resistant efflux pump.

  DOI：

  10.1021/np000166d

文献信息

• PYRONE ANALOG COMPOSITIONS AND METHODS
  申请人：Robbins Wendye

  公开号：US20090258939A1

  公开（公告）日：2009-10-15

  Novel pyrone analogs are described which can enhance the effectiveness of a therapeutic agent when administered and/or reduce side effects caused by the administration of a therapeutic agent.
• [EN] PYRONE ANALOG COMPOSITIONS AND METHODS<br/>[FR] COMPOSITIONS ET PROCÉDÉS D'ANALOGUES DE PYRONE
  申请人：LIMERICK BIOPHARMA INC

  公开号：WO2009018320A1

  公开（公告）日：2009-02-05

  Novel pyrone analogs are described which can enhance the effectiveness of a therapeutic agent when administered and/or reduce side effects caused by the administration of a therapeutic agent.
• [EN] PYRONE ANALOG COMPOSITIONS AND METHODS<br/>[FR] COMPOSITIONS D'ANALOGUES DE PYRONE ET PROCÉDÉS
  申请人：LIMERICK BIOPHARMA INC

  公开号：WO2009018350A1

  公开（公告）日：2009-02-05

  Novel pyrone analogs are described which can enhance the effectiveness of a therapeutic agent when administered and/or reduce side effects caused by the administration of a therapeutic agent.
• Synthesis and Structures of Regioisomeric Hydnocarpin-Type Flavonolignans
  作者：Nathan R. Guz、Frank R. Stermitz

  DOI：10.1021/np000166d

  日期：2000.8.1

  Flavonolignans represent natural compounds whose biosynthesis presumes a radical coupling of a ring B catecholic flavonoid with a molecule of coniferyl alcohol or an analogue. Many natural flavonolignans can exist as regioisomers, depending on how the coupled coniferyl alcohol moiety orients to the flavonoid. These regioisomers are often difficult to separate and have virtually identical NMR spectra. Structural assignments for some have changed with time or have been given without proof. We here report syntheses of both regioisomers of the flavonolignan hydnocarpin and one isomer of a plant isolate previously known as 5'-methoxyhydnocarpin. This isomer, here renamed 5'-methoxyhydnocarpin-D, was recently shown to be a potent inhibitor of a Staphylococcus aureus multidrug resistant efflux pump.