1-[2,6-Dihydroxy-4-(methoxymethoxy)-3,5-bis(3-methylbut-2-enyl)phenyl]ethanone | 1044743-41-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[2,6-Dihydroxy-4-(methoxymethoxy)-3,5-bis(3-methylbut-2-enyl)phenyl]ethanone
• CAS: 1044743-41-0
• 化学式: C₂₀H₂₈O₅
• 分子量: 348.439
• InChiKey: LMWKNIPLUOCLBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-[2,6-Dihydroxy-4-(methoxymethoxy)-3,5-bis(3-methylbut-2-enyl)phenyl]ethanone 、 硫酸二甲酯 在 sodium hydroxide 、 四丁基碘化铵 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 24.0h， 以71%的产率得到2-hydroxy-4-methoxymethyl-6-methoxy-3,5-diprenylacetophenone
  参考文献：
  名称：

  Synthesis, Cytotoxicity, and Antioxidative Activity of Minor Prenylated Chalcones from Humulus lupulus

  摘要：

  The minor hop (Humulus lupulus) chalcones 3'-geranylchalconaringenin (3), 5'-prenylxanthohumol (4), flavokawin (5), xanthohumol H (8), xanthohumol C (9), and 1 '',2 ''-dihydroxanthohumol C (10) were synthesized. The non-natural chalcones 3'-geranyl-6'-O-methylchalconaringenin (2), 3'-methylflavokawin (6), and 2'-O-methyl-3'-prenylchalconar-. ingenin (7) were also synthesized. Cytotoxicity was investigated in HeLa cells, and these compounds all had IC50 values comparable to xanthohumol (8.2-19.2 mu M). The ORAC-fluorescein assay revealed potent antioxidative activity for 7 and 8 with 5.2 and 4.8 Trolox equivalents, respectively.

  DOI：

  10.1021/np800188b
• 作为产物：
  描述：

  1-[4-(Methoxymethoxy)-2,6-bis(3-methylbut-2-enoxy)phenyl]ethanone 在 N,N-二甲基苯胺 作用下， 反应 3.0h， 以40%的产率得到1-[2,6-Dihydroxy-4-(methoxymethoxy)-3,5-bis(3-methylbut-2-enyl)phenyl]ethanone
  参考文献：
  名称：

  Synthesis, Cytotoxicity, and Antioxidative Activity of Minor Prenylated Chalcones from Humulus lupulus

  摘要：

  The minor hop (Humulus lupulus) chalcones 3'-geranylchalconaringenin (3), 5'-prenylxanthohumol (4), flavokawin (5), xanthohumol H (8), xanthohumol C (9), and 1 '',2 ''-dihydroxanthohumol C (10) were synthesized. The non-natural chalcones 3'-geranyl-6'-O-methylchalconaringenin (2), 3'-methylflavokawin (6), and 2'-O-methyl-3'-prenylchalconar-. ingenin (7) were also synthesized. Cytotoxicity was investigated in HeLa cells, and these compounds all had IC50 values comparable to xanthohumol (8.2-19.2 mu M). The ORAC-fluorescein assay revealed potent antioxidative activity for 7 and 8 with 5.2 and 4.8 Trolox equivalents, respectively.

  DOI：

  10.1021/np800188b

文献信息

• Synthesis, Cytotoxicity, and Antioxidative Activity of Minor Prenylated Chalcones from <i>Humulus lupulus</i>
  作者：Susanne Vogel、Jörg Heilmann

  DOI：10.1021/np800188b

  日期：2008.7.1

  The minor hop (Humulus lupulus) chalcones 3'-geranylchalconaringenin (3), 5'-prenylxanthohumol (4), flavokawin (5), xanthohumol H (8), xanthohumol C (9), and 1 '',2 ''-dihydroxanthohumol C (10) were synthesized. The non-natural chalcones 3'-geranyl-6'-O-methylchalconaringenin (2), 3'-methylflavokawin (6), and 2'-O-methyl-3'-prenylchalconar-. ingenin (7) were also synthesized. Cytotoxicity was investigated in HeLa cells, and these compounds all had IC50 values comparable to xanthohumol (8.2-19.2 mu M). The ORAC-fluorescein assay revealed potent antioxidative activity for 7 and 8 with 5.2 and 4.8 Trolox equivalents, respectively.