3-(pentadecen-10'(Z)-yl)phenol | 936109-16-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-(pentadecen-10'(Z)-yl)phenol
• 英文别名: 3-(10'(Z)-pentadecenyl)phenol；3-pentadec-10'-Z-enyl phenol；3-(10'Z-pentadecenyl)phenol；3-[(Z)-pentadec-10-enyl]phenol
• CAS: 936109-16-9
• 化学式: C₂₁H₃₄O
• 分子量: 302.5
• InChiKey: QSNFYOWSNHPPKG-WAYWQWQTSA-N

物化性质

• 沸点：
  419.8±14.0 °C(Predicted)
• 密度：
  0.919±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  22
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(pentadecen-10'(Z)-yl)phenol 在 碘 作用下， 以 乙醚 为溶剂， 反应 24.5h， 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

• New class of acetylcholinesterase inhibitors from the stem bark of Knema laurina and their structural insights
  作者：Muhammad Nadeem Akhtar、Kok Wai Lam、Faridah Abas、Maulidiani、Syahida Ahmad、Syed Adnan Ali Shah、Atta-ur-Rahman、M. Iqbal Choudhary、Nordin Hj Lajis

  DOI：10.1016/j.bmcl.2011.04.065

  日期：2011.7

  Bioassay-guided extraction of the stem bark of Knema laurina showed the acetylcholinesterase (AChE) inhibitory activity of DCM and hexane fractions. Further repeated column chromatography of hexane and DCM fractions resulted in the isolation and purification of five alkenyl phenol and salicylic acid derivatives. New compounds, (+)-2-hydroxy-6-(10'-hydroxypentadec-8'(E)-enyl)benzoic acid (1) and 3-pentadec-10'(Z)-enylphenol (2), along with known 3-heptadec-10'(Z)-enylphenol (3), 2-hydroxy-6-(pentadec-10'(Z)-enyl)benzoic acid (4), and 2-hydroxy-6-(10'(Z)-heptadecenyl)benzoic acid (5) were isolated from the stem bark of this plant. Compounds (1-5) were tested for their acetylcholinesterase inhibitory activity. The structures of these compounds were elucidated by the 1D and 2D NMR spectroscopy, mass spectrometry and chemical derivatizations. Compound 5 showed strong acetylcholinesterase inhibitory activity with IC50 of 0.573 +/- 0.0260 mu M. Docking studies of compound 5 indicated that the phenolic compound with an elongated side chain could possibly penetrate deep into the active site of the enzyme and arrange itself through p-p interaction, H-bonding, and hydrophobic contacts with some critical residues along the complex geometry of the active gorge. (C) 2011 Elsevier Ltd. All rights reserved.
• 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.