8-benzyloxy-4,9-dimethylpsoralen | 1228691-34-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 8-benzyloxy-4,9-dimethylpsoralen
• 英文别名: 3,5-Dimethyl-9-phenylmethoxyfuro[3,2-g]chromen-7-one
• CAS: 1228691-34-6
• 化学式: C₂₀H₁₆O₄
• 分子量: 320.345
• InChiKey: CAYDNXVYQRITMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-benzyloxy-4,9-dimethylpsoralen 在 5% Pd(II)/C(eggshell) 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 以90%的产率得到4,4'-dimethylxanthotoxol
  参考文献：
  名称：

  Synthesis of methyl-substituted xanthotoxol to clarify prooxidant effect of methyl on radical-induced oxidation of DNA

  摘要：

  4-Methyl-8-hydroxylpsoralen (MXan) and 4,9-dimethy1-8-hydroxylpsoralen (DMXan) were synthesized in order to clarify the effect of methyl on the antioxidant effectiveness of xanthotoxol (8-hydroxyl-psoralen, Xan), which were assessed by bleaching beta-carotene in linoleic acid-Triton emulsion, by interacting with 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS(+))center dot, 2,2'-dipheny1-1-picrylhydrazyl radical (DPPH), and galvinoxyl radical, and by protecting DNA against the oxidation induced by Cu(2+)/glutathione (GSH) and 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH). Methyl attaching to xanthotoxol did not affect its ability to protect linoleic acid against autoxidation and to inhibit Cu(2+)/GSH-induced oxidation DNA, but decreased its ability to scavenge ABTS(+)center dot and DPPH, and to protect DNA against AAPH-induced oxidation. Therefore, methyl attenuated the antioxidant effectiveness of xanthotoxol in radical-induced oxidation of DNA.

  DOI：

  10.1016/j.ejmech.2010.02.044
• 作为产物：
  描述：

  4-methyl-7-acetylmethoxy-8-benzyloxycoumarin 在 水 、 sodium hydroxide 作用下， 反应 2.0h， 以72%的产率得到8-benzyloxy-4,9-dimethylpsoralen
  参考文献：
  名称：

  Synthesis of methyl-substituted xanthotoxol to clarify prooxidant effect of methyl on radical-induced oxidation of DNA

  摘要：

  4-Methyl-8-hydroxylpsoralen (MXan) and 4,9-dimethy1-8-hydroxylpsoralen (DMXan) were synthesized in order to clarify the effect of methyl on the antioxidant effectiveness of xanthotoxol (8-hydroxyl-psoralen, Xan), which were assessed by bleaching beta-carotene in linoleic acid-Triton emulsion, by interacting with 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS(+))center dot, 2,2'-dipheny1-1-picrylhydrazyl radical (DPPH), and galvinoxyl radical, and by protecting DNA against the oxidation induced by Cu(2+)/glutathione (GSH) and 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH). Methyl attaching to xanthotoxol did not affect its ability to protect linoleic acid against autoxidation and to inhibit Cu(2+)/GSH-induced oxidation DNA, but decreased its ability to scavenge ABTS(+)center dot and DPPH, and to protect DNA against AAPH-induced oxidation. Therefore, methyl attenuated the antioxidant effectiveness of xanthotoxol in radical-induced oxidation of DNA.

  DOI：

  10.1016/j.ejmech.2010.02.044

文献信息

• Synthesis of methyl-substituted xanthotoxol to clarify prooxidant effect of methyl on radical-induced oxidation of DNA
  作者：Chuan Xiao、Zhi-Guang Song、Zai-Qun Liu

  DOI：10.1016/j.ejmech.2010.02.044

  日期：2010.6

  4-Methyl-8-hydroxylpsoralen (MXan) and 4,9-dimethy1-8-hydroxylpsoralen (DMXan) were synthesized in order to clarify the effect of methyl on the antioxidant effectiveness of xanthotoxol (8-hydroxyl-psoralen, Xan), which were assessed by bleaching beta-carotene in linoleic acid-Triton emulsion, by interacting with 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS(+))center dot, 2,2'-dipheny1-1-picrylhydrazyl radical (DPPH), and galvinoxyl radical, and by protecting DNA against the oxidation induced by Cu(2+)/glutathione (GSH) and 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH). Methyl attaching to xanthotoxol did not affect its ability to protect linoleic acid against autoxidation and to inhibit Cu(2+)/GSH-induced oxidation DNA, but decreased its ability to scavenge ABTS(+)center dot and DPPH, and to protect DNA against AAPH-induced oxidation. Therefore, methyl attenuated the antioxidant effectiveness of xanthotoxol in radical-induced oxidation of DNA.