2,2',4'-trihydroxy-4-methoxychalcone | 125538-07-0

• 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: 2,2',4'-trihydroxy-4-methoxychalcone
• 英文别名: (E)-1-(2,4-dihydroxyphenyl)-3-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one
• CAS: 125538-07-0
• 化学式: C₁₆H₁₄O₅
• 分子量: 286.284
• InChiKey: IXSDMVZSYFSIKC-XVNBXDOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2',4'-trihydroxy-4-methoxychalcone 在 polyphenol oxidase 、 双氧水 、 三羟甲基氨基甲烷盐酸盐 作用下， 以 乙二醇甲醚 为溶剂， 生成 6-Hydroxy-2-[1-hydroxy-1-(2-hydroxy-4-methoxy-phenyl)-meth-(Z)-ylidene]-benzofuran-3-one 、 7-Hydroxy-2-(2-hydroxy-4-methoxy-phenyl)-chroman-4-one 、 6-Hydroxy-2-[1-(2-hydroxy-4-methoxy-phenyl)-meth-(E)-ylidene]-benzofuran-3-one 、 6-Hydroxy-2-[1-(2-hydroxy-4-methoxy-phenyl)-meth-(Z)-ylidene]-benzofuran-3-one
  参考文献：
  名称：

  Studies in Cell Suspension Cultures of Cassia didymobotrya. Part VI. The Biotransformation of Chalcones to Aurones and Auronols

  摘要：

  Cell-free extracts derived from tissue cultures of Cassia didymobotrya, which previously had been reported to convert 4-hydroxychalcones to flavones and biflavanones, catalyze the biotransformation of 2-hydroxychalcones to aurones and auronols. The aurone was shown to be the direct precursor of auronol.

  DOI：

  10.3987/com-96-7414
• 作为产物：
  描述：

  2-羟基-4-甲氧基苯甲醛 、 2,4-二羟基苯乙酮 在 氢氧化钾 作用下， 以 甲醇 、 水 为溶剂， 反应 0.75h， 以45%的产率得到2,2',4'-trihydroxy-4-methoxychalcone
  参考文献：
  名称：

  Studies in Cell Suspension Cultures of Cassia didymobotrya. Part VI. The Biotransformation of Chalcones to Aurones and Auronols

  摘要：

  Cell-free extracts derived from tissue cultures of Cassia didymobotrya, which previously had been reported to convert 4-hydroxychalcones to flavones and biflavanones, catalyze the biotransformation of 2-hydroxychalcones to aurones and auronols. The aurone was shown to be the direct precursor of auronol.

  DOI：

  10.3987/com-96-7414

文献信息

• Biosynthesis of optically active Diels–Alder type adducts revealed by an aberrant metabolism of O-methylated precursors in Morus alba cell cultures
  作者：Yoshio Hano、Taro Nomura、Shinichi Ueda

  DOI：10.1039/c39900000610

  日期：——

  Addition of O-methylated chalcone, as precursors, to Morus alba cell cultures has resulted in the formation of optically active O-methyl derivatives of chalcomoracin (1) and kuwanon J (2), corroborating the pivotal step of the biosynthesis of (1) and (2) to be the enzymic Diels–Alder reaction.

  将O-甲基化的查尔酮作为前体添加到桑属桑树细胞培养物中，导致形成了查考莫拉星（1）和kuwanon J（2）的光学活性O-甲基衍生物，从而证实了（1）的生物合成的关键步骤。（2）是酶的Diels-Alder反应。
• Studies in Cell Suspension Cultures of Cassia didymobotrya. Part VI. The Biotransformation of Chalcones to Aurones and Auronols
  作者：Bruno Botta、Giuliano Delle Monache、Maria Cristina De Rosa、Rosalba Scurria、Alberto Vitali、Vittorio Vinciguerra、Pilar Menendez、Domenico Misiti

  DOI：10.3987/com-96-7414

  日期：——

  Cell-free extracts derived from tissue cultures of Cassia didymobotrya, which previously had been reported to convert 4-hydroxychalcones to flavones and biflavanones, catalyze the biotransformation of 2-hydroxychalcones to aurones and auronols. The aurone was shown to be the direct precursor of auronol.