8-hydroxy-7-methoxyisoflavone | 855627-11-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 8-hydroxy-7-methoxyisoflavone
• 英文别名: 8-hydroxy-7-methoxy-3-phenyl-chromen-4-one；8-Hydroxy-7-methoxy-3-phenyl-chromen-4-on；8-Hydroxy-7-methoxy-3-phenylchromen-4-one
• CAS: 855627-11-1
• 化学式: C₁₆H₁₂O₄
• 分子量: 268.269
• InChiKey: CQQVMFDJEHVCOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 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：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

ADMET

代谢

生物chanin A已知的人类代谢物包括(2S,3S,4S,5R)-3,4,5-三羟基-6-(7-甲氧基-4-氧代-3-苯基香豆素-8-基)氧代氧杂环己烷-2-羧酸。

Biochanin A has known human metabolites that include (2S,3S,4S,5R)-3,4,5-trihydroxy-6-(7-methoxy-4-oxo-3-phenylchromen-8-yl)oxyoxane-2-carboxylic acid.

来源:NORMAN Suspect List Exchange

反应信息

• 作为反应物：
  描述：

  8-hydroxy-7-methoxyisoflavone 在 sodium hydroxide 、 sodium persulfate 作用下， 生成 5,8-dihydroxy-7-methoxy-3-phenyl-chromen-4-one
  参考文献：
  名称：

  Ishwar-Dass et al., Proceedings - Indian Academy of Sciences, Section A, 1953, # 37, p. 599,608

  摘要：

  DOI：
• 作为产物：
  描述：

  7,8-二甲氧基-3-苯基-4H-1-苯并吡喃-4-酮 在 氢碘酸 、 乙酸酐 作用下， 生成 8-hydroxy-7-methoxyisoflavone
  参考文献：
  名称：

  Ishwar-Dass et al., Proceedings - Indian Academy of Sciences, Section A, 1953, # 37, p. 599,608

  摘要：

  DOI：

文献信息

• Synthesis of Various Kinds of Isoflavones, Isoflavanes, and Biphenyl-Ketones and Their 1,1-Diphenyl-2-picrylhydrazyl Radical-Scavenging Activities
  作者：Hideyuki Goto、Yoshiyasu Terao、Shuji Akai

  DOI：10.1248/cpb.57.346

  日期：——

  Forty-eight kinds of isoflavones (8), thirty-one isoflavanes (9), and forty-seven biphenyl-ketones (10, 10′) were synthesized from eleven kinds of substituted phenols (11) and six phenylacetic acids (12). Among them, seventy-five compounds are new. The radical scavenging activities of these compounds were evaluated using 1,1-diphenyl-2-picrylhydrazyl (DPPH) at pH 6.0. We found that thirty-nine out of forty-three compounds having a catechol moiety on either the A- or the B-ring exhibited a high activity (ED50=12—54 μM) similar to that of catechin. In these cases, the remaining part of their structure seemed to have little effect on their activity. Many 6- or 8-hydroxyisoflavanes (9E—I) and their biphenyl-ketone derivatives (10E—H) also showed a high activity (ED50=<50 μM), while all of their corresponding isoflavones (8E—I) were not active at all. The 7-hydroxyisoflavanes having either an additional hydroxyl group at the C5-position (9D) or a methoxy group at the C6-position (9J) presented a high activity (ED50=26—32 μM). This study suggests that natural isoflavones have the possibilities of exhibiting antioxidant activities through the hydroxylation at the C6-, C8-, or C3′-position or the formation of the isoflavanes (9) and/or the biphenyl-ketone derivatives (10′) by metabolism or biotransformation.

  合成了四十八种异黄酮（8）、三十一种异黄烷（9）以及四十七种联苯酮（10, 10′），这些化合物是由十一种取代酚（11）和六种苯乙酸（12）合成的。其中，有七十五种化合物是新发现的。这些化合物的自由基清除活性在pH 6.0下使用1,1-二苯基-2-吡唑啉酮（DPPH）进行了评估。我们发现，在四十三种含有儿茶酚基的化合物中，三十九种在A环或B环上表现出与儿茶素相似的高活性（ED50=12—54 μM）。在这些情况下，它们结构的其他部分似乎对活性影响不大。许多6-或8-羟基异黄烷（9E—I）及其联苯酮衍生物（10E—H）也显示出高活性（ED50=<50 μM），而它们对应的异黄酮（8E—I）则完全没有活性。具有在C5位增加羟基（9D）或在C6位增加甲氧基（9J）的7-羟基异黄烷则展现出高活性（ED50=26—32 μM）。本研究表明，天然异黄酮通过在C6、C8或C3′位置的羟基化，或通过代谢或生物转化形成异黄烷（9）和/或联苯酮衍生物（10′），具有表现抗氧化活性的可能性。