(Z)-3-[2,2-Dimethyl-8-(3-methyl-but-2-enyl)-2H-chromen-6-yl]-acrylic acid

• 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: (Z)-3-[2,2-Dimethyl-8-(3-methyl-but-2-enyl)-2H-chromen-6-yl]-acrylic acid
• 英文别名: (Z)-3-[2,2-dimethyl-8-(3-methylbut-2-enyl)chromen-6-yl]prop-2-enoic acid
• 化学式: C₁₉H₂₂O₃
• 分子量: 298.382
• InChiKey: ZKUFWHYBAKVWMB-VURMDHGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-3-(2,2-dimethyl-8-prenyl-2H-1-benzopyran-6-yl)-2-propenoic acid 以 甲醇 为溶剂， 反应 288.0h， 生成 (Z)-3-[2,2-Dimethyl-8-(3-methyl-but-2-enyl)-2H-chromen-6-yl]-acrylic acid
  参考文献：
  名称：

  Enhanced Cytotoxicity in a Z-Photoisomer of a Benzopyran Derivative of Propolis

  摘要：

  (Z)-2,2-Dimethyl-8-(3-methyl-2-butenyl) acid (1) was isolated from Brazilian propolis, together with-the known benzopyran derivative, (E)-2,2-dimethyl-8-(3-met-2-butenyl)-benzopyran-6-propenoic acid (2). The structure was determined by spectroscopic analyses, which included 1D and 2D H-1 and C-13 NMR experiments, as well as MS, IR, and UV spectroscopy, Compound 2 rapidly changed to 1 under UV irradiation conditions (365 nm), and. the reverse reaction was also observed. The ratio of 1 to 2 reached 2.3 when the reaction began from either 1 or 2, indicating a photostationary state. Compound 1 displayed an approximate 7-fold stronger cytotoxicity against human lung carcinoma cells (HPLC-2) compared with 2.

  DOI：

  10.1021/np990463m

文献信息

• [EN] PHYSIOLOGIC ACTIVITY OF A BENZOPYRAN DERIVATIVE ORIGINATING FROM PROPOLIS<br/>[FR] ACTIVITE PHYSIOLOGIQUE D'UN DERIVE DE BENZOPYRANE ISSU DE LA PROPOLIS
  申请人：HIROTA MIKAKO

  公开号：WO2001060359A1

  公开（公告）日：2001-08-23

  Antitumor agents containing as the active ingredient compound (I), 2,2-dimethyl-8-(3-methyl-2-butenyl)benzopyran-6-cis-propenoic acid, or pharmaceutically acceptable salts thereof. Compound (I) is an enantiomeric benzopyran derivative obtained from propolis through purification and being useful as an antitumor agent and excellent in safeness.