3,5,6,7,8,4‘-六甲氧基黄酮 | 34170-18-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 3,5,6,7,8,4‘-六甲氧基黄酮
• 英文名称: 3,5,6,7,8,4′-hexamethoxyflavone
• 英文别名: 3,4',5,6,7,8-hexamethoxyflavone；3,5,6,7,8,4'-hexamethoxyflavone；5,6,7,8,3,4'-hexamethoxyflavone；auranetin 5-methyl ether；auranetin-5-methyl ether；nobiletin；3-Methoxytangeretin；3,5,6,7,8-pentamethoxy-2-(4-methoxyphenyl)chromen-4-one
• CAS: 34170-18-8
• 化学式: C₂₁H₂₂O₈
• 分子量: 402.401
• InChiKey: OBIOZWXPDBWYHB-UHFFFAOYSA-N

物化性质

• 熔点：
  133-134 °C
• 沸点：
  598.8±50.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  81.7
• 氢给体数：
  0
• 氢受体数：
  8

安全信息

• 储存条件：
  储存条件：2-8°C，避光保存，需置于干燥环境中并密封。

制备方法与用途

3,5,6,7,8-五甲氧基黄酮是α-淀粉酶的抑制剂，在500 μM浓度下的抑制活性为28.3%。

反应信息

• 作为反应物：
  描述：

  3,5,6,7,8,4‘-六甲氧基黄酮 在 氢氧化钾 作用下， 生成 2-hydroxy-3,4,5,6,ο-pentamethoxyacetophenone
  参考文献：
  名称：

  Seshadri; Venkateswarlu, Proceedings - Indian Academy of Sciences, Section A, 1946, # 23, p. 192,200

  摘要：

  DOI：
• 作为产物：
  描述：

  野漆树苷 在 Oxone 、 N-溴代丁二酰亚胺(NBS) 、 碳酸氢钠 、 sodium carbonate 、 potassium carbonate 、 三氟乙酸 、 copper(I) bromide 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 21.0h， 生成 3,5,6,7,8,4‘-六甲氧基黄酮
  参考文献：
  名称：

  Synthesis of Citrus polymethoxyflavonoids and their antiproliferative activities on Hela cells

  摘要：

  A series of polymethoxyflavonoids (3-16) were synthesized through dehydrogenation, O-methylation, glycoside hydrolysis, bromination, microwave-assisted aromatic nucleophilic substitution, dimethyldioxirane oxidation and regioselective demethylation, starting from abundant and inexpensive natural sources naringin and hesperidin. All the synthetic compounds were test for antiproliferative activities on human cervical carcinoma Hela cell line by the standard CCK-8 assay, the result showed that most of the target compounds exhibited moderate to potent antiproliferative activities on Hela cells comparable with the positive control cis-Platin. Among them, 5-hydroxypolymethoxy flavonoid 13 showed the strongest activity (IC50 0.791 mu M).

  DOI：

  10.1007/s00044-017-1871-4

文献信息

• Semisynthesis of Polymethoxyflavonoids from Naringin and Hesperidin
  作者：Yue Li、Shuanglian Cai、Kailin He、Qiuan Wang

  DOI：10.3184/174751914x13966139490181

  日期：2014.5

  glycoside hydrolysis, dehydrogenation, bromination, aromatic nucleophilic substitution, O-methylation, dimethyldioxirane oxidation and regioselective demethylation, starting from abundant and inexpensive natural sources naringin and hesperidin. A new synthetic method for selective methylation using CuBr catalysed and microwave-assisted reaction was developed, and the dimethyl dioxirane oxidation of

  多甲氧基黄酮 (PMF) 具有重要的生物活性，尤其是作为抗癌剂。通过糖苷水解、脱氢、溴化、芳香亲核取代、O-甲基化、二甲基二环氧乙烷氧化和区域选择性去甲基化，从丰富且廉价的天然来源柚皮苷和橙皮苷开始，进行了一系列 PMF 的半合成。开发了一种利用CuBr催化和微波辅助反应进行选择性甲基化的新合成方法，大大改善了黄酮向黄酮醇的二甲基二环氧乙烷氧化。新的半合成路线具有原料易得、操作简单、收率好等优点。
• Studies of the Selective O-Alkylation and Dealkylation of Flavonoids. XIX. A Convenient Method for Synthesizing 3,5,6,7,8-Pentaoxygenated Flavones.
  作者：Tokunaru HORIE、Yasuhiko KAWAMURA、Hitoshi YAMAMOTO、Kazuyo YAMASHITA

  DOI：10.1248/cpb.43.2054

  日期：——

  The methoxymethyl ethers of 6-hydroxy-5, 7, 8-trimethoxyflavones, which were derived from 2', 5'-dihydroxy-3', 4', 6'-trimethoxyacetophenone, were oxidized with dimethyldioxirane to give the corresponding 3-hydroxyflavones. Selective O-alkylation and dealkylation of the 3-hydroxyflavones were examined and a convenient method for synthesizing the following ten kinds of 3, 5, 6, 7, 8-pentaoxygenated flavones was established : 3-hydroxy-5, 6, 7, 8-tetramethoxyflavones, 3, 5-dihydroxy-6, 7, 8-trimethoxyflavones, 3, 6-dihydroxy-5, 7, 8-trimethoxyflavones, 3, 5, 6-trihydroxy-7, 8-dimethoxyflavones, 3, 5, 6, 7-tetrahydroxy-8-methoxyflavones, and their 3-methyl ethers. Furthermore, 3, 5, 8-trihydroxy-4', 6, 7-trimethoxyflavone, 3, 8-dihydroxy-4', 5, 6, 7-tetramethoxyflavone, and 5, 8-dihydroxy-3, 6, 7-trimethoxyflavones were similarly synthesized and their spectral properties were examined. Additionally, the proposed structures of three natural flavones were revised.

  由 2'，5'-二羟基-3'，4'，6'-三甲氧基苯乙酮衍生的 6-羟基-5，7，8-三甲氧基黄酮的甲氧基甲基醚经二甲基二氧环己烷氧化得到相应的 3-羟基黄酮。研究了 3-羟基黄酮的选择性 O-烷基化和脱烷基化，并建立了合成以下十种 3、5、6、7、8-五氧根黄酮的简便方法：3-羟基-5，6，7，8-四甲氧基黄酮、3，5-二羟基-6，7，8-三甲氧基黄酮、3，6-二羟基-5，7，8-三甲氧基黄酮、3，5，6-三羟基-7，8-二甲氧基黄酮、3，5，6，7-四羟基-8-甲氧基黄酮及其 3-甲基醚。此外，还合成了 3, 5, 8-三羟基-4', 6, 7-三甲氧基黄酮、3, 8-二羟基-4', 5, 6, 7-四甲氧基黄酮和 5, 8-二羟基-3, 6, 7-三甲氧基黄酮，并研究了它们的光谱特性。此外，还对三种天然黄酮的拟议结构进行了修订。
• Murti et al., Proceedings - Indian Academy of Sciences, Section A, 1946, # 24, p. 233,236
  作者：Murti et al.

  DOI：——

  日期：——
• Synthesis and antiproliferative activities of thioxoflavonoids on three human cancer cells
  作者：Wei Li、Peipei Han、Shuanglian Cai、Qiuan Wang

  DOI：10.1080/14786419.2018.1448812

  日期：2019.9.2

  Two series of fifteen novel thioxoflavonoids 2a-2h and 4a-4g were synthesized from corresponding flavonoids 1a-1h and 3a-3g by reacting with Lawesson's reagent, respectively. Their in vitro antiproliferative activities were evaluated on a panel of three human cancer cell lines (Hela, HCC1954 and SK-OV-3) using cell counting kit-8 (CCK-8) assay. The results showed that most of the target compounds exhibited moderate to good antiproliferative activities against the three human cancer cell lines. In particular, thioxoflavonoids 2f and 2g showed the strongest antiproliferative activity on all three human cancer cell lines with IC50 values ranging from 3.34 to 4.67 mu M, 4f showed the best antiproliferative activity on Hela cells (IC50 2.30 mu M), 2e showed the best antiproliferative activity on HCC1954 cells (IC50 2.13 mu M) and SK-OV-3 cells (IC50 2.33 mu M). The antiproliferative activities may be involved in their antioxidant activity, which can be speculated by their ability to scavenge free radicals and by their capacity of affecting key redox enzymes.[GRAPHICS].
• Über einen neuen Flavonfarbstoff
  作者：Walter Karrer

  DOI：10.1002/hlca.193401701198

  日期：——