5,7-dihydroxy-2-((4Z,7Z,10Z,13Z,16Z)-nonadeca-4,7,10,13,16-pentaen-1-yl)-4H-chromen-4-one | 82513-77-7

• 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-((4Z,7Z,10Z,13Z,16Z)-nonadeca-4,7,10,13,16-pentaen-1-yl)-4H-chromen-4-one
• 英文别名: 5,7-dihydroxy-2-((4Z,7Z,10Z,13Z,16Z)-nonadeca-4,7,10,13,16-pentaenyl)-4H-chromen-4-one；(all-Z)-5',7'-dihydroxy-2'-nonadeca-4,7,10,13,16-pentenyl-chromone；5,7-dihydroxy-2-(4Z,7Z,10Z,13Z,16Z-nonadecapentaenyl)chromone；5,7-dihydroxy-2-[(4Z,7Z,10Z,13Z,16Z)-nonadeca-4,7,10,13,16-pentaenyl]chromen-4-one
• CAS: 82513-77-7
• 化学式: C₂₈H₃₄O₄
• 分子量: 434.576
• InChiKey: WHXFGTNLJWUZDQ-JLNKQSITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 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-((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
• 作为产物：
  描述：

  在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 3.0h， 以90%的产率得到5,7-dihydroxy-2-((4Z,7Z,10Z,13Z,16Z)-nonadeca-4,7,10,13,16-pentaen-1-yl)-4H-chromen-4-one
  参考文献：
  名称：

  首次全合成从褐藻 Zonaria Tournefortii 中分离出的多不饱和色酮代谢物

  摘要：

  以二十碳五烯酸乙酯为原料，首次全合成海洋天然产物全-( Z )-5,7-二羟基-2-( 4Z , 7Z , 10Z , 13Z , 16Z-十九碳五烯基)色酮经过六个步骤得到，总产率为 14%。

  DOI：

  10.1021/ol802635a

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
• First Total Synthesis of a Polyunsaturated Chromone Metabolite Isolated from the Brown Algae <i>Zonaria tournefortii</i>
  作者：Hany F. Anwar、Trond Vidar Hansen

  DOI：10.1021/ol802635a

  日期：2009.2.5

  Starting from the ethyl ester of eicosapentaenoic acid, the first total synthesis of the marine natural product all-(Z)-5,7-dihydroxy-2-(4Z,7Z,10Z,13Z,16Z-nonadecapentaenyl)chromone has been achieved in six steps and in 14% overall yield.

  以二十碳五烯酸乙酯为原料，首次全合成海洋天然产物全-( Z )-5,7-二羟基-2-( 4Z , 7Z , 10Z , 13Z , 16Z-十九碳五烯基)色酮经过六个步骤得到，总产率为 14%。
• 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.