(E)-3-(3,4-dihydroxybenzylidene)-5,7-dihydroxychroman-4-one | 1469538-09-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮
• 英文名称: (E)-3-(3,4-dihydroxybenzylidene)-5,7-dihydroxychroman-4-one
• 英文别名: ovatifolionone；(3E)-3-[(3,4-dihydroxyphenyl)methylidene]-5,7-dihydroxychromen-4-one
• CAS: 1469538-09-7
• 化学式: C₁₆H₁₂O₆
• 分子量: 300.268
• InChiKey: GSXUMSFRTKYHFT-YCRREMRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• 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：

  (E)-3-(3,4-dihydroxybenzylidene)-5,7-dihydroxychroman-4-one 、 乙酸酐 在 吡啶 作用下， 以1.8 mg的产率得到(E)-3-(3,4-dihydroxybenzylidene)-5-acetoxy-7-hydroxychroman-4-one
  参考文献：
  名称：

  COX-2 inhibitory activity of homoisoflavanones and xanthones from the bulbs of the Southern African Ledebouria socialis and Ledebouria ovatifolia (Hyacinthaceae: Hyacinthoideae)

  摘要：

  The bulbs of Ledebouria socialis (Hyacinthaceae) yielded the benzocyclobutene homoisoflavonoid, (R)-2',5-dihydroxy-3',4',7-trimethoxyspiro{2H-1-benzopyran-3-(4H)-9-bicyclo[4.2.0]octa[1,3,5]triene}-4-one, socialinone (1). Ledebouria ovatzfolia yielded (2 epsilon,3R)-2,5-dihydroxy-7-methoxyspiro[2H-1-benzopyran-3(4H), 5'(6'H)-cyclobuta[f][1,3]benzodioxol]-4-one (2) and the homoisoflavanone, (E)-3-(3',4'-dihydroxybenzylidene)-5,7-dihydroxychroman-4-one, ovatifolionone (5), the dihydrochalcone, 4,4'-dihydroxy-2',6'-dimethoxydihydrochalcone (3), and xanthone, 1,6-dihydroxy-2,3,5-trimethoxy-8-methyl-9H-xanthen-9-one (4) along with 21 known compounds. Structures were determined using spectroscopic techniques. The anti-inflammatory activities of the homoisoflavonoids and xanthones isolated were evaluated against cyclooxygenase-1 and -2 isoenzymes. (R)-3-(3',4'-Dihydroxybenzyl)-7-hydroxy-5-methoxychroman-4-one (7), (E)-3-(3',4'-dihydroxybenzylidene)-7-hydroxy-5-methoxychroman-4-one (10), 1,3,6-trihydroxy-2-methoxy-8-methylxanthen-9-one (6) and ovatifolionone acetate (5Ac) exhibited significant activity against cyclooxygenase-2 at <10 mu M. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2013.06.024