5-(十七碳-12-烯基)间苯二酚 | 103462-06-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 5-(十七碳-12-烯基)间苯二酚
• 英文名称: 12’Z-5-heptadec-12’-enylresorcinol
• 英文别名: (12Z)-5-(heptadec-12-enyl)resorcinol；5-(12-cis-heptadecenyl)-resorcinol；5-(12-Z-heptadecenyl)-resorcinol；5-(12'Z-heptadecenyl)resorcinol；5-(14'Z-heptadecenyl)resorcinol；5-(Heptadec-12-enyl)resorcinol；5-[(Z)-heptadec-12-enyl]benzene-1,3-diol
• CAS: 103462-06-2
• 化学式: C₂₃H₃₈O₂
• 分子量: 346.554
• InChiKey: KDUIMXINOLVPCT-WAYWQWQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  25
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(十七碳-12-烯基)间苯二酚 在 碘 作用下， 以 乙醚 为溶剂， 反应 26.0h， 生成
  参考文献：
  名称：

  Characterisation of triterpenes and new phenolic lipids in Cameroonian propolis

  摘要：

  Chemical investigation of a sample of propolis originating from North-Western Cameroon led to the isolation of thirteen alk(en)ylphenols (1-13) (inseparable mixture) along with alpha-amyrin (14), beta-amyrin (15), lupeol (16), cycloartenol (17), mangiferonic acid (18), ambonic acid (19), mangiferolic acid (20), ambolic acid (21), isomangiferolic acid (22) and nine alk(en)ylresorcinols (23-31) (inseparable mixture). All compounds were identified following analysis of their spectroscopic data and comparison with previously published reports. Compounds (8), (12), (13) and (30) are new natural products. GC-MS analysis carried out on the alk(en)ylphenol and alk(en)ylresorcinol mixtures (dimethyl disulphide trimethylsilyl derivatives) revealed the presence of saturated and mono-unsaturated compounds with side chain lengths ranging from C11 to C19 and C15 to C19, respectively. The position of the double bond in mono-unsaturated derivatives was established from the characteristic fragments resulting from the cleavage of the bond between the two methylthio-substituted carbons. The most abundant compound in each mixture was 3-(12'Z-heptadecenyl)-phenol (10) and 5-(12'Z-heptadecenyl)-resorcinol (29). This study is the first to report the presence of triterpenes (except for lupeol) and phenolic lipids, including eighteen compounds previously unreported in bee glue, in an African sample. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2014.07.016

文献信息

• Characterisation of triterpenes and new phenolic lipids in Cameroonian propolis
  作者：M.N. Kardar、T. Zhang、G.D. Coxon、D.G. Watson、J. Fearnley、V. Seidel

  DOI：10.1016/j.phytochem.2014.07.016

  日期：2014.10

  Chemical investigation of a sample of propolis originating from North-Western Cameroon led to the isolation of thirteen alk(en)ylphenols (1-13) (inseparable mixture) along with alpha-amyrin (14), beta-amyrin (15), lupeol (16), cycloartenol (17), mangiferonic acid (18), ambonic acid (19), mangiferolic acid (20), ambolic acid (21), isomangiferolic acid (22) and nine alk(en)ylresorcinols (23-31) (inseparable mixture). All compounds were identified following analysis of their spectroscopic data and comparison with previously published reports. Compounds (8), (12), (13) and (30) are new natural products. GC-MS analysis carried out on the alk(en)ylphenol and alk(en)ylresorcinol mixtures (dimethyl disulphide trimethylsilyl derivatives) revealed the presence of saturated and mono-unsaturated compounds with side chain lengths ranging from C11 to C19 and C15 to C19, respectively. The position of the double bond in mono-unsaturated derivatives was established from the characteristic fragments resulting from the cleavage of the bond between the two methylthio-substituted carbons. The most abundant compound in each mixture was 3-(12'Z-heptadecenyl)-phenol (10) and 5-(12'Z-heptadecenyl)-resorcinol (29). This study is the first to report the presence of triterpenes (except for lupeol) and phenolic lipids, including eighteen compounds previously unreported in bee glue, in an African sample. (C) 2014 Elsevier Ltd. All rights reserved.