3,3',4,4'-四羟基-2-甲氧基查尔酮 | 197227-39-7

• 物质功能分类: 有机原料 - 酮类化合物
• 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
• 中文名称: 3,3',4,4'-四羟基-2-甲氧基查尔酮
• 英文名称: tetrahydroxymethoxychalcone
• 英文别名: (E)-3-(3,4-dihydroxy-2-methoxyphenyl)-1-(3,4-dihydroxyphenyl)prop-2-en-1-one；3,3',4,4'-Tetrahydroxy-2-methoxychalcone
• CAS: 197227-39-7
• 化学式: C₁₆H₁₄O₆
• 分子量: 302.284
• InChiKey: BICPGUILWBQAEY-GORDUTHDSA-N

物化性质

• 物理描述：
  Solid
• 熔点：
  196°C

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 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：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  硫酸二甲酯 、 3,3',4,4'-四羟基-2-甲氧基查尔酮 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以0.2 mg的产率得到(2E)-1-(3,4-dimethoxyphenyl)-3-(2,3,4-trimethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Phenolic Constituents of Liquorice. VII. A New Chalcone with a Potent Radical Scavenging Activity and Accompanying Phenolics from Liquorice.

  摘要：

  从东北地区的商业甘草中分离出23种酚类化合物，包括6种新化合物。新化合物的结构分别为2-7，分别命名为四羟基甲氧基查尔酮、异吡喃香豆素、甘草黄酮醇A、甘草异黄酮A、B和C。在从甘草中分离出的多酚类化合物中，化合物2对1,1-二苯基-2-苦基肼自由基的清除效果最强。在碱性二甲基亚砜溶液中，化合物2的空气氧化作用产生了强烈的ESR信号，表明由化合物2形成的自由基物种具有稳定性。

  DOI：

  10.1248/cpb.45.1485
• 作为产物：
  描述：

  3,4-双(乙氧基甲氧基)苯甲醛 在 重铬酸吡啶 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 39.0h， 生成 3,3',4,4'-四羟基-2-甲氧基查尔酮
  参考文献：
  名称：

  항염증 활성을 나타내는 신규 리코찰콘 유사체 화합물

  摘要：

  利可查孔被认为具有多种生物活性。然而，大多数利可查孔表现出细胞毒性。具有共同取代基的苯环B的利可查孔B和D已成为改变苯环A结构的靶点。这些合成的利可查孔类似物（化合物1~6）在抑制NO生成方面分别显示出9.94、4.72、10.1、4.85、2.37和4.95 μM的IC50值。

  公开号：

  KR101533010B1

文献信息

• 항염증 활성을 나타내는 신규 리코찰콘 유사체 화합물
  申请人：Industry Academic Cooperation Foundation, Hallym University 한림대학교 산학협력단(220070195175) BRN ▼221-82-10284

  公开号：KR101533010B1

  公开（公告）日：2015-07-02

  리코찰콘은 다양한 생물학적 활성을 가진다고 알려져 있다. 그러나, 대부분의 리코찰콘은 세포독성을 나타낸다. 방향족 링 B에서 공통적인 치환기를 갖는 리코찰콘 B와 D는 염증 연구에서 방향족 링 A의 구조를 변형하기 위해 타겟이 되었다. 이와 같이 제조된 리코찰콘 유도체 (화합물 1~6)은 NO 생성 억제능을 비교하여 각각 9.94, 4.72, 10.1, 4.85, 2.37 및 4.95 μM의 IC50 값을 나타내었다.

  利可查孔被认为具有多种生物活性。然而，大多数利可查孔表现出细胞毒性。具有共同取代基的苯环B的利可查孔B和D已成为改变苯环A结构的靶点。这些合成的利可查孔类似物（化合物1~6）在抑制NO生成方面分别显示出9.94、4.72、10.1、4.85、2.37和4.95 μM的IC50值。
• COMPOSITION FOR PREVENTING OR TREATING MUSCULAR DISEASES, CONTAINING, AS ACTIVE INGREDIENT, GLYCYRRHIZA URALENSIS EXTRACT OR COMPOUND ISOLATED THEREFROM
  申请人：RESEARCH COOPERATION FOUNDATION OF YEUNGNAM UNIVERSITY

  公开号：US20210315957A1

  公开（公告）日：2021-10-14

  A pharmaceutical composition and a health functional food composition for preventing, treating, or improving muscular diseases have licorice extract or a fraction thereof, or a compound isolated therefrom or a pharmaceutically acceptable salt thereof, as an active ingredient. The licorice extract or a fraction thereof, the compound or salt thereof induce the myoblasts proliferation and promote the differentiation into myotubes, and since the licorice extract or a fraction thereof, the compound or salt thereof has an excellent effect on regenerating damaged muscles, various muscle diseases are effectively prevented, improved or treated using the composition.
• Synthesis of licochalcone analogues with increased anti-inflammatory activity
  作者：Si-Jun Kim、Cheol Gi Kim、So-Ra Yun、Jin-Kyung Kim、Jong-Gab Jun

  DOI：10.1016/j.bmcl.2013.11.044

  日期：2014.1

  Licohalcones have been reported to have various biological activities. However, most of licochalcones also showed cytotoxicity even though their versitile utilities. Licochalcones B and D, which have common substituents at aromatic ring B, are targeted to modify the structure at aromatic ring A for inflammatory studies. Licochalcone derivatives (1-6) thus prepared are compared for their suppression ability of nitric oxide (NO) production and showed 9.94, 4.72, 10.1, 4.85, 2.37 and 4.95 mu M of IC50 values, respectively. (C) 2013 Elsevier Ltd. All rights reserved.
• Phenolic Constituents of Liquorice. VII. A New Chalcone with a Potent Radical Scavenging Activity and Accompanying Phenolics from Liquorice.
  作者：Tsutomu HATANO、Miyuki TAKAGI、Hideyuki ITO、Takashi YOSHIDA

  DOI：10.1248/cpb.45.1485

  日期：——

  Twenty-three phenolics including six new compounds were isolated from a commercial liquorice from North-eastern China. Structures 2-7 were assigned for the new compounds, designated as tetrahydroxy-methoxychalcone, isolicopyranocoumarin, glycyrrhiza-flavonol A, and glycyrrhiza-isoflavones A, B and C, respectively. Compound 2 showed the most potent scavenging effect on 1, 1-diphenyl-2-picrylhydrazyl radical among the tested polyphenols isolated from liquorice. Air-oxidation of 2 in alkaline dimethylsulfoxide solution gave strong ESR signals, indicating the stability of the radical species formed from 2.

  从东北地区的商业甘草中分离出23种酚类化合物，包括6种新化合物。新化合物的结构分别为2-7，分别命名为四羟基甲氧基查尔酮、异吡喃香豆素、甘草黄酮醇A、甘草异黄酮A、B和C。在从甘草中分离出的多酚类化合物中，化合物2对1,1-二苯基-2-苦基肼自由基的清除效果最强。在碱性二甲基亚砜溶液中，化合物2的空气氧化作用产生了强烈的ESR信号，表明由化合物2形成的自由基物种具有稳定性。