3-geranyl-6-hydroxy-2,4-dimethoxymethylacetophenone | 1044743-38-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-geranyl-6-hydroxy-2,4-dimethoxymethylacetophenone
• 英文别名: 1-[3-[(2E)-3,7-dimethylocta-2,6-dienyl]-6-hydroxy-2,4-bis(methoxymethoxy)phenyl]ethanone
• CAS: 1044743-38-5
• 化学式: C₂₂H₃₂O₆
• 分子量: 392.492
• InChiKey: UDJQRTFZMLOYEW-MHWRWJLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-geranyl-6-hydroxy-2,4-dimethoxymethylacetophenone 、 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89%的产率得到3-geranyl-2,4-dimethoxymethyl-6-methoxyacetophenone
  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-[2-[(2E)-3,7-dimethylocta-2,6-dienoxy]-4,6-bis(methoxymethoxy)phenyl]ethanone 在 N,N-二甲基苯胺 作用下， 反应 3.0h， 以23%的产率得到3-geranyl-6-hydroxy-2,4-dimethoxymethylacetophenone
  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.