7-methoxy-3-(4'-hydroxybenzylidene)chroman-4-one | 5526-53-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 高异黄酮
• 英文名称: 7-methoxy-3-(4'-hydroxybenzylidene)chroman-4-one
• 英文别名: 3-(4'-hydroxybenzylidene)-7-methoxychroman-4-one；3-[(4-Hydroxyphenyl)methylidene]-7-methoxychromen-4-one；3-[(4-hydroxyphenyl)methylidene]-7-methoxychromen-4-one
• CAS: 5526-53-4
• 化学式: C₁₇H₁₄O₄
• 分子量: 282.296
• InChiKey: LZEBZDHKLPFOHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对羟基苯甲醛 、 4H-1-苯并吡唑-4-酮 在 哌啶 作用下， 反应 10.0h， 生成 7-methoxy-3-(4'-hydroxybenzylidene)chroman-4-one
  参考文献：
  名称：

  Properties of Synthetic Homoisoflavonoids To Reduce Oxidants and To Protect Linoleic Acid and DNA against Oxidation

  摘要：

  3-(2'-, 3'-, and 4'-Hydroxybenzylidene)-7-methoxychroman-4-one (o-, m-, and p-HBMC) was synthesized for the clarification of the influence of the hydroxyl group at the B ring on the antioxidant activity of homoisoflavonoid. The three homoisoflavonoids used herein can reduce peroxynitrite. p-HBMC exhibited high activity to reduce singlet oxygen. Furthermore, o-, m-, and p-HBMC can scavenge the 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS(center dot+)) and 2,2'-diphenyl-1-picryl-hydrazyl (DPPH) and galvinoxyl radicals. The rates of o-HBMC trapping of DPPH and galvinoxyl radicals were higher than those of m- and p-HBMC, whereas m-HBMC can trap ABTS rapidly. o-HBMC was found to possess high activity in the beta-carotene linoleic acid bleaching test and to protect methyl linoleate against 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH)-induced oxidation efficiently. Finally, o-HBMC served as a prooxidant in Cu2+/glutathione (GSH)- and hydroxyl radical-mediated oxidations of DNA. m- and p-HBMC protected DNA against hydroxyl radical-mediated oxidation of DNA effectively, and o- and p-HBMC behaved as antioxidants to protect DNA against AAPH-induced oxidation. Thus, the hydroxyl group attaching to the ortho- and para-positions in the B ring was of importance for the homoisoflavonoid's enhancement of antioxidant activity.

  DOI：

  10.1021/jf904089q

文献信息

• Sathyanarayana, S.; Krishnamurty, H. G., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 899 - 901
  作者：Sathyanarayana, S.、Krishnamurty, H. G.

  DOI：——

  日期：——
• Properties of Synthetic Homoisoflavonoids To Reduce Oxidants and To Protect Linoleic Acid and DNA against Oxidation
  作者：Yan-Feng Li、Zai-Qun Liu、Xu-Yang Luo

  DOI：10.1021/jf904089q

  日期：2010.4.14

  3-(2'-, 3'-, and 4'-Hydroxybenzylidene)-7-methoxychroman-4-one (o-, m-, and p-HBMC) was synthesized for the clarification of the influence of the hydroxyl group at the B ring on the antioxidant activity of homoisoflavonoid. The three homoisoflavonoids used herein can reduce peroxynitrite. p-HBMC exhibited high activity to reduce singlet oxygen. Furthermore, o-, m-, and p-HBMC can scavenge the 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS(center dot+)) and 2,2'-diphenyl-1-picryl-hydrazyl (DPPH) and galvinoxyl radicals. The rates of o-HBMC trapping of DPPH and galvinoxyl radicals were higher than those of m- and p-HBMC, whereas m-HBMC can trap ABTS rapidly. o-HBMC was found to possess high activity in the beta-carotene linoleic acid bleaching test and to protect methyl linoleate against 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH)-induced oxidation efficiently. Finally, o-HBMC served as a prooxidant in Cu2+/glutathione (GSH)- and hydroxyl radical-mediated oxidations of DNA. m- and p-HBMC protected DNA against hydroxyl radical-mediated oxidation of DNA effectively, and o- and p-HBMC behaved as antioxidants to protect DNA against AAPH-induced oxidation. Thus, the hydroxyl group attaching to the ortho- and para-positions in the B ring was of importance for the homoisoflavonoid's enhancement of antioxidant activity.