5,6,7-trihydroxy-4'-methoxy-isoflavine

• 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: 5,6,7-trihydroxy-4'-methoxy-isoflavine
• 英文别名: 5,6,7-trihydroxy-4'-methoxyisoflavone；6-hydroxybiochanin A monohydrate；6-hydroxybiochanin A；5,6,7-trihydroxy-4'-methoxyisoflavone monohydrate；4'-Methoxyscutellarein；5,6,7-Trihydroxy-3-(4-methoxyphenyl)chromen-4-one
• 化学式: C₁₆H₁₂O₆
• 分子量: 300.268
• InChiKey: DXRCZIARKKLMLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 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：
  96.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-[2,4-Dimethoxy-3,6-bis(phenylmethoxy)phenyl]-3,3-dimethoxy-2-(4-methoxyphenyl)propan-1-one 在 palladium on activated charcoal 盐酸 、 三氯化铝 、 氢气 作用下， 以 吡啶 、 甲醇 、 乙酸乙酯 为溶剂， 反应 0.5h， 生成 5,6,7-trihydroxy-4'-methoxy-isoflavine
  参考文献：
  名称：

  Studies of the Selective O-Alkylation and Dealkylation of Flavonoids.XX. A Convenient Method for Synthesizing 5,6,7-Trihydroxyisoflavones and 5,6-Dihydroxy-7-methoxyisoflavones.

  摘要：

  3',6'-双(苄氧基)-2',4'-二甲氧基查尔酮，源自3,6-二羟基-2,4-二甲氧基乙酰苯酮的二苄醚，在甲醇中通过氧化性重排与硝酸铊(III)(TTN)反应，生成2-芳基-1-[3,6-双(苄氧基)-2,4-二甲氧基苯基]-3,3-二甲氧基丙酮；这些产物通过氢解后环化转化为6-羟基-5,7-二甲氧基异黄酮。异黄酮的乙酸酯中的5-甲氧基在乙腈中以5%（质量体积比）无水溴化铝选择性裂解，定量得到相应的5-羟基异黄酮，这些异黄酮再水解为5,6-二羟基-7-甲氧基异黄酮。乙酸酯还通过在70°C下乙腈中30%（质量体积比）无水氯化铝处理36-48小时脱甲基化，得到5,6,7-三羟基异黄酮。对这些异黄酮的光谱特性进行了检验，并鉴定了一些天然异黄酮。

  DOI：

  10.1248/cpb.44.486

文献信息

• Inhibition of Extrahepatic Human Cytochromes P450 1A1 and 1B1 by Metabolism of Isoflavones Found in <i>Trifolium pratense</i> (Red Clover)
  作者：Dean W. Roberts、Daniel R. Doerge、Mona I. Churchwell、Gonçalo Gamboa da Costa、M. Matilde Marques、William H. Tolleson

  DOI：10.1021/jf049418x

  日期：2004.10.1

  Biochanin A and formononetin are the predominant isoflavones in red clover. In a previous study (J. Agric. Food Chem. 2002, 50, 4783-4790), it was demonstrated that human liver microsomes converted biochanin A and formononetin to genistein and daidzein. This paper now shows CYP1B1-catalyzed O-demethylation of biochanin A and formononetin to produce genistein and daidzein, respectively, which inhibit

  红三叶草中主要的异黄酮是Biochanin A和formononetin。在先前的研究中（J. Agric。Food Chem。2002，50，4783-4790），已证明人肝微粒体将生物素A和formononetin转化为染料木黄酮和黄豆苷元。现在，本文显示了CYP1B1催化的生物素A和formononetin的O-去甲基化分别产生染料木黄酮和黄豆苷元，它们分别抑制CYP1B1。将重组人CYP1A1或CYP1B1与biochanin A或formononetin一起孵育。CYP1A1催化异黄酮4'-O-去甲基化和羟基化的效率相似，而CYP1B1则比羟基化更倾向于4'-O-去甲基化。三种生物chanin A代谢产物（5,7,3'-三羟基-4'-甲氧基异黄酮，5,7,8-三羟基-4'-甲氧基异黄酮和5,6,7-三羟基-4' -甲氧基异黄酮）通过1 H NMR光谱和质谱进行表征。大豆苷元（Ki
• Formation of polyhydroxylated isoflavones from the isoflavones genistein and biochanin A by bacteria isolated from tempe
  作者：Klaus Klus、Wolfgang Barz

  DOI：10.1016/s0031-9422(98)80069-1

  日期：1998.3
• Hydrogen bonding and π–π stacking in 6-hydroxybiochanin A monohydrate
  作者：Zun-Ting Zhang、Yan-Chang Wang

  DOI：10.1107/s0108270106044908

  日期：2007.1.15

  In the lattice of the title compound (systematic name: 5,6,7-trihydroxy-40-methoxyisoflavone monohydrate), C16H12O6 center dot H2O, the isoflavone molecules are linked into chains through R-4(3)(17) motifs composed via O-H center dot center dot center dot O and C-H center dot center dot center dot O hydrogen bonds. Centrosymmetric R-4(2)(14) motifs assemble the chains into sheets. Hydrogen-bonding and aromatic pi-pi stacking interactions lead to the formation of a three-dimensional network structure.
• Studies of the Selective O-Alkylation and Dealkylation of Flavonoids.XX. A Convenient Method for Synthesizing 5,6,7-Trihydroxyisoflavones and 5,6-Dihydroxy-7-methoxyisoflavones.
  作者：Tokunaru HORIE、Masahiro SASAGAWA、Fumihito TORII、Yasuhiko KAWAMURA、Kazuyo YAMASHITA

  DOI：10.1248/cpb.44.486

  日期：——

  3', 6'-Bis(benzyloxy)-2', 4'-dimethoxychalcones, which were derived from dibenzyl ether of 3, 6-dihydroxy-2, 4-dimethoxyacetophenone, were oxidatively rearranged with thallium(III) nitrate (TTN) in methanol to give 2-aryl-1-[3, 6-bis(benzyloxy)-2, 4-dimethoxyphenyl]-3, 3-dimethoxypropan-1-ones; these products were converted into 6-hydroxy-5, 7-dimethoxyisoflavones by hydrogenolysis followed by cyclization. The 5-methoxy group in the acetates of the isoflavones was selectively cleaved with 5% (w/v) anhydrous aluminum bromide in acetonitrile to give quantitatively the corresponding 5-hydroxyisoflavones, which were hydrolyzed to 5, 6-dihydroxy-7-methoxy-isoflavones. The acetates were also demethylated to 5, 6, 7-trihydroxyisoflavones with 30% (w/v) anhydrous aluminum chloride in acetonitrile at 70°C for 36-48 h. The spectral properties of these isoflanones were examined and some natural isoflavones were identified.

  3',6'-双(苄氧基)-2',4'-二甲氧基查尔酮，源自3,6-二羟基-2,4-二甲氧基乙酰苯酮的二苄醚，在甲醇中通过氧化性重排与硝酸铊(III)(TTN)反应，生成2-芳基-1-[3,6-双(苄氧基)-2,4-二甲氧基苯基]-3,3-二甲氧基丙酮；这些产物通过氢解后环化转化为6-羟基-5,7-二甲氧基异黄酮。异黄酮的乙酸酯中的5-甲氧基在乙腈中以5%（质量体积比）无水溴化铝选择性裂解，定量得到相应的5-羟基异黄酮，这些异黄酮再水解为5,6-二羟基-7-甲氧基异黄酮。乙酸酯还通过在70°C下乙腈中30%（质量体积比）无水氯化铝处理36-48小时脱甲基化，得到5,6,7-三羟基异黄酮。对这些异黄酮的光谱特性进行了检验，并鉴定了一些天然异黄酮。