艾纳香素 B | 79995-67-8

• 物质功能分类: 天然产物 - 黄酮类化合物
• 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: 艾纳香素 B
• 中文别名: 艾纳香素B；4(1H)-吡啶酮,3-甲氧基-1-甲基-,腙
• 英文名称: 4',7-di-O-methyldihydroquercetin
• 英文别名: 5,3',3-trihydroxy-7,4'-dimethoxyflavanone；3',5-dihydroxy-4',7-dimethoxydihydroflavonol；(2R,3R)-(+)-4',7-di-O-methyldihydroquercetin；(+)-7,4'-di-O-methyltaxifolin；(2R,3R)-dihydroquercetin-4',7-di-O-methyl ether；3,5,4'-trihydroxy-7,5'-dimethoxyflavanone；7,4^,-dimethoxydihydroquercetin；7,4^,-dimethoxytaxifolin；7,4′-O-dimethyltaxifolin；(2R,3R)-3,5,3'-trihydroxy-7,4'-dimethoxyflavanone；(+)-4',7-di-O-methyl-2,3-trans-dihydroquercetin；Blumeatin B；(2R,3R)-3,5-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-methoxy-2,3-dihydrochromen-4-one
• CAS: 79995-67-8
• 化学式: C₁₇H₁₆O₇
• 分子量: 332.31
• InChiKey: SVPNMFZMHPLGRR-DLBZAZTESA-N

物化性质

• 熔点：
  165-167 °C
• 沸点：
  627.8±55.0 °C(Predicted)
• 密度：
  1.445±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  重氮甲烷 、 花旗松素 以 乙醚 、 苯 为溶剂， 反应 1.5h， 以28%的产率得到李属素
  参考文献：
  名称：

  Structure–Activity Relationship for (+)-Taxifolin Isolated from Silymarin as an Inhibitor of Amyloid β Aggregation

  摘要：

  Silymarin, the seed extract of Silybium marianum, has preventive effects against Alzheimer's disease-like pathogenesis in vivo. We isolated (+)-taxifolin (4) from silymarin as an inhibitor of aggregation of the 42-residue amyloid beta-protein. Structure-activity relationship studies revealed the 3',4'-dihydroxyl groups to be critical to the anti-aggregative ability, whereas the 7-hydroxyl group and the stereochemistry at positions 2 and 3 were not important.

  DOI：

  10.1271/bbb.120925

文献信息

• Methylation of Dihydroquercetin Acetates:  Synthesis of 5-<i>O</i>-Methyldihydroquercetin
  作者：Eberhard Kiehlmann、Peter W. Slade

  DOI：10.1021/np034005w

  日期：2003.12.1

  The major products of methylation of dihydroquercetin (1, dhq) with diazomethane have been identified as 7-O-methyldhq (9), 7,3'-di-0-methyldhq (10), 7,4'-di-O-methyldhq (11), and 7,3',4'-tri-O-methyldhq (2). With dhq 3,7,3',4'-tetraacetate (6), dhq 3,5,3',4'-tetraacetate (5), dhq 3,3',4'-triacetate (7), dhq 7,3',4'triacetate (8), and dhq 3-acetate (4) the same reaction affords mainly 5-O-methyldhq 3,7,3',4'-tetraacetate (15), 7-O-methyldhq 3,5,3',4'-tetraacetate (13), 7-O-methyldhq 3,3',4'-triacetate (14), 5-O-methyldhq 7,3',4'triacetate (25), and 7-O-methyldhq 3-acetate (12), respectively. The methylation of 8 is accompanied by intermolecular acetyl migration from phenolic oxygen to the hydroxy group of the heterocyclic ring. 5-O-Methyldhq (28) is accessible by deacetylation of 25. 5,7-Di-O-methyldhq (29), four known methyl ethers, 13 new and three known methyl ether acetates of dhq, and six new isomers with 2,3-cis stereochemistry were spectroscopically identified.
• Structure–Activity Relationship for (+)-Taxifolin Isolated from Silymarin as an Inhibitor of Amyloid β Aggregation
  作者：Mizuho SATO、Kazuma MURAKAMI、Mayumi UNO、Haruko IKUBO、Yu NAKAGAWA、Sumie KATAYAMA、Ken-ichi AKAGI、Kazuhiro IRIE

  DOI：10.1271/bbb.120925

  日期：2013.5.23

  Silymarin, the seed extract of Silybium marianum, has preventive effects against Alzheimer's disease-like pathogenesis in vivo. We isolated (+)-taxifolin (4) from silymarin as an inhibitor of aggregation of the 42-residue amyloid beta-protein. Structure-activity relationship studies revealed the 3',4'-dihydroxyl groups to be critical to the anti-aggregative ability, whereas the 7-hydroxyl group and the stereochemistry at positions 2 and 3 were not important.