5,7-dihydroxy-2-nonadecyl-4H-chromen-4-one | 82513-79-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 5,7-dihydroxy-2-nonadecyl-4H-chromen-4-one
• 英文别名: 5,7-dihydroxy-2-nonadecyl-chromone；5,7-Dihydroxy-2-nonadecylchromone；5,7-dihydroxy-2-nonadecylchromen-4-one
• CAS: 82513-79-9
• 化学式: C₂₈H₄₄O₄
• 分子量: 444.655
• InChiKey: ADSQBWKZBXPZNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  32
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,7-dihydroxy-2-nonadecyl-4H-chromen-4-one 、 碘甲烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 12.0h， 以89%的产率得到5,7-dimethoxy-2-nonadecyl-4H-chromen-4-one
  参考文献：
  名称：

  Polyunsaturated fatty acid-derived chromones exhibiting potent antioxidant activity

  摘要：

  The marine polyunsaturated lipid-derived natural product all-(Z)-5,7-dihydroxy-2-(4Z,7Z,10Z,13Z,16Z-nonadecapentaenyl) (1) and four analogs 5-8 have been synthesized and evaluated as antioxidants in two cell-based assays. The natural product 1 and the analog 5 exhibited interesting antioxidant effects with IC50-values of 14 +/- 9 and 29 +/- 3 mu M, respectively, in a cellular lipid peroxidation antioxidant activity assay using HepG2 cells. Moreover, in the HepG2 cellular antioxidant activity assay, the natural product 1 exhibited strong protective effects against reactive oxygen species with an IC50 = 160 +/- 25 mu M. (C) 2013 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2013.03.003
• 作为产物：
  描述：

  5,7-dihydroxy-2-((4Z,7Z,10Z,13Z,16Z)-nonadeca-4,7,10,13,16-pentaen-1-yl)-4H-chromen-4-one 在 5%-palladium/activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 以98%的产率得到5,7-dihydroxy-2-nonadecyl-4H-chromen-4-one
  参考文献：
  名称：

  Polyunsaturated fatty acid-derived chromones exhibiting potent antioxidant activity

  摘要：

  The marine polyunsaturated lipid-derived natural product all-(Z)-5,7-dihydroxy-2-(4Z,7Z,10Z,13Z,16Z-nonadecapentaenyl) (1) and four analogs 5-8 have been synthesized and evaluated as antioxidants in two cell-based assays. The natural product 1 and the analog 5 exhibited interesting antioxidant effects with IC50-values of 14 +/- 9 and 29 +/- 3 mu M, respectively, in a cellular lipid peroxidation antioxidant activity assay using HepG2 cells. Moreover, in the HepG2 cellular antioxidant activity assay, the natural product 1 exhibited strong protective effects against reactive oxygen species with an IC50 = 160 +/- 25 mu M. (C) 2013 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2013.03.003

文献信息

• Two chrome derivatives from the brown alga
  作者：Corrado Tringali、Mario Piatelli

  DOI：10.1016/s0040-4039(00)87145-2

  日期：1982.1
• Polyunsaturated fatty acid-derived chromones exhibiting potent antioxidant activity
  作者：Yasser M.A. Mohamed、Anders Vik、Tim Hofer、Jeanette Hammer Andersen、Trond Vidar Hansen

  DOI：10.1016/j.chemphyslip.2013.03.003

  日期：2013.5

  The marine polyunsaturated lipid-derived natural product all-(Z)-5,7-dihydroxy-2-(4Z,7Z,10Z,13Z,16Z-nonadecapentaenyl) (1) and four analogs 5-8 have been synthesized and evaluated as antioxidants in two cell-based assays. The natural product 1 and the analog 5 exhibited interesting antioxidant effects with IC50-values of 14 +/- 9 and 29 +/- 3 mu M, respectively, in a cellular lipid peroxidation antioxidant activity assay using HepG2 cells. Moreover, in the HepG2 cellular antioxidant activity assay, the natural product 1 exhibited strong protective effects against reactive oxygen species with an IC50 = 160 +/- 25 mu M. (C) 2013 Elsevier Ireland Ltd. All rights reserved.