5,6,7-trihydroxy-3,4'-dimethoxyflavone

• 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: 5,6,7-trihydroxy-3,4'-dimethoxyflavone
• 英文别名: 5,6,7-trihydroxy-3-methoxy-2-(4-methoxyphenyl)chromen-4-one
• 化学式: C₁₇H₁₄O₇
• 分子量: 330.294
• InChiKey: JQRLBMPXYSUXBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5,6,7-trihydroxy-3,4'-dimethoxyflavone 、 乙酸酐 以0%的产率得到
  参考文献：
  名称：

  Horie Tokunaru, Tominaga Hideaki, Yoshida Isao, Kawamura Yasuhiko, Bull. Chem. Soc. Jap., 66 (1993) N 3, S 877-881

  摘要：

  DOI：
• 作为产物：
  描述：

  6-hydroxy-3,5,7-trimethoxy-2-(4-methoxy-phenyl)-chromen-4-one 在 aluminum tri-bromide 作用下， 以 乙腈 为溶剂， 反应 8.0h， 生成 5,6,7-trihydroxy-3,4'-dimethoxyflavone
  参考文献：
  名称：

  黄酮类化合物的选择性 O-烷基化和脱烷基化研究。十四。一种由 6-羟基-3,5,7-三甲氧基黄酮合成 5,6,7-三羟基-3-甲氧基黄酮的简便方法

  摘要：

  研究了 6-羟基-3,5,7-三甲氧基黄酮及其乙酸酯的去甲基化，并发现了以下结果。6-羟基-3,4',5,7-四甲氧基黄酮与 30% 无水氯化铝的乙腈溶液脱甲基反应得到 5,6-二羟基-3,4',7-三甲氧基黄酮和 5,6,7-三羟基的混合物-3,4'-二甲氧基黄酮，但其乙酸酯的去甲基化形成了 5,6,7-三羟基黄酮作为主要产物。后一反应可用作合成 5,6,7-三羟基-3-甲氧基黄酮的一般方法。另一方面，6-羟基-3,4',5,7-四甲氧基黄酮与 10% 无水溴化铝在乙腈中的脱甲基反应得到 5,6,7-三羟基黄酮作为主要产物，4'-甲氧基，该反应更适用于合成5,6,7-三羟基黄酮。

  DOI：

  10.1246/bcsj.66.877

文献信息

• Studies of the Selective<i>O</i>-Alkylation and Dealkylation of Flavonoids. XVIII. A Convenient Method for Synthesizing 3,5,6,7-Tetrahydroxyflavones
  作者：Tokunaru Horie、Takashi Kobayashi、Yasuhiko Kawamura、Isao Yoshida、Hideaki Tominaga、Kazuyo Yamashita

  DOI：10.1246/bcsj.68.2033

  日期：1995.7

  In the demethylation of 6-hydroxy-3,4′,7-trimethoxy-5-(tosyloxy)flavone with anhydrous aluminum bromide, the 5-tosyloxyl group was eliminated with bromination to give 8-bromo-3,6,7-trihydroxy-4′-methoxyflavone as the main product. When anhydrous aluminum chloride was used in the demethylation of the acetate, the 5-tosyloxyl group was cleaved prior to the demethylation to give 5,6,7-trihydroxy-3,4′-dimethoxyflavone. Demethylation of 6-hydroxy-4′,5,7-trimethoxy-3-(tosyloxy)flavone and its acetate with the bromide or chloride afforded the 5,6,7-trihydroxyflavone without the cleavage of the 3-tosyloxyl group, but was not suitable for the general synthesis of the 3,5,6,7-tetrahydroxyflavones because of the difficulty in removing the protecting group. Consequently, it was found that the direct demethylation of 3,6-dihydroxy-5,7-dimethoxyflavones with anhydrous aluminum chloride–sodium iodide in acetonitrile was the most useful general method for synthesizing 3,5,6,7-tetrahydroxyflavones. Additionally, the reported structures of two natural flavones were revised.

  在无水溴化铝的脱甲基反应中，6-羟基-3,4′,7-三甲氧基-5-(托烯氧基)黄酮的5-托烯氧基基团在溴化作用下被消除，生成8-溴-3,6,7-三羟基-4′-甲氧基黄酮作为主要产物。当使用无水氯化铝进行醋酸酯的脱甲基反应时，5-托烯氧基基团在脱甲基前被切断，生成5,6,7-三羟基-3,4′-二甲氧基黄酮。6-羟基-4′,5,7-三甲氧基-3-(托烯氧基)黄酮及其醋酸酯与溴化物或氯化物的脱甲基反应生成5,6,7-三羟基黄酮，而不切断3-托烯氧基基团，但由于去除保护基团的困难，不适合于3,5,6,7-四羟基黄酮的一般合成。因此，发现采用无水氯化铝-碘化钠在乙腈中对3,6-二羟基-5,7-二甲氧基黄酮进行直接脱甲基反应是合成3,5,6,7-四羟基黄酮的最有效的一般方法。此外，修订了两种天然黄酮的已报告结构。
• Oral compositions and use thereof
  申请人：——

  公开号：US20040057908A1

  公开（公告）日：2004-03-25

  The present invention relates to an oral composition which includes an organoleptically suitable carrier and an amount of a terpenoid and a flavonoid, dispersed in the carrier, which is effective to prevent or treat dental caries, dental plaque formation, gingivitis, candidiasis, dental stomatitis, aphthous ulceration, or fungal infection. The invention also relates to various uses of oral compositions, containing a terpenoid, a flavonoid, or both, such uses include: inhibiting the activity of surface-bound glusosyltransferase; treating or inhibiting dental caries, gingivitis, candidiasis, denture stomatitis; inhibiting the accumulation of microorganisms on an oral surface; and/or treating or inhibiting aphthous ulcerations on an oral surface.

  本发明涉及一种口服组合物，该组合物包括一种有机性适宜的载体以及一定量的萜类化合物和黄酮类化合物，它们分散在载体中，可有效预防或治疗龋齿、牙菌斑形成、牙龈炎、念珠菌病、牙齿口腔炎、口腔溃疡或真菌感染。本发明还涉及含有萜类化合物、类黄酮或两者的口服组合物的各种用途，这些用途包括：抑制表面结合的葡糖基转移酶的活性；治疗或抑制龋齿、牙龈炎、念珠菌病、义齿口腔炎；抑制微生物在口腔表面的积聚；和/或治疗或抑制口腔表面的阿弗他溃疡。
• ORAL COMPOSITIONS AND USE THEREOF
  申请人：University of Rochester

  公开号：EP1399119A2

  公开（公告）日：2004-03-24
• FLAVONOIDDERIVAT ZUR BEHANDLUNG VON ZAHNKARIES
  申请人：Mühlbauer Technology GmbH

  公开号：EP4017585A1

  公开（公告）日：2022-06-29
• [EN] ORAL COMPOSITIONS AND USE THEREOF<br/>[FR] COMPOSITIONS A ADMINISTRATION ORALE ET LEURS APPLICATIONS
  申请人：UNIV ROCHESTER

  公开号：WO2002047615A2

  公开（公告）日：2002-06-20

  The present invention relates to an oral composition which includes an organoleptically suitable carrier and an amount of a terpenoid and a flavonoid, dispersed in the carrier, which is effective to prevent or treat dental caries, dental plaque formation, gingivitis, candidiasis, dental stomatitis, aphthous ulceration, or fungal infection. The invention also relates to various uses of oral compositions, containing a terpenoid, a flavonoid, or both, such uses include: inhibiting the activity of surface-bound glusosyltransferase; treating or inhibiting dental caries, gingivitis, candidiasis, denture stomatitis; inhibiting the accumulation of microorganisms on an oral surface; and/or treating or inhibiting aphthous ulcerations on an oral surface.