5-(11′Z-heptadecenyl)resorcinol | 1008777-54-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-(11′Z-heptadecenyl)resorcinol
• 英文别名: 5-(11'-Z-heptadecenyl)-resorcinol；5-(11'Z-heptadecenyl)resorcinol；5-[(Z)-heptadec-11-enyl]benzene-1,3-diol
• CAS: 1008777-54-5
• 化学式: C₂₃H₃₈O₂
• 分子量: 346.554
• InChiKey: HUHFXXDYKXJMCS-SREVYHEPSA-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-(11′Z-heptadecenyl)resorcinol 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

• Anti-inflammatory 5-(11′Z-heptadecenyl)- and 5-(8′Z,11′Z-heptadecadienyl)-resorcinols from mango (Mangifera indica L.) peels
  作者：Matthias Knödler、Jürgen Conrad、Eva M. Wenzig、Rudolf Bauer、Markus Lacorn、Uwe Beifuss、Reinhold Carle、Andreas Schieber

  DOI：10.1016/j.phytochem.2007.10.013

  日期：2008.2

  Bioassay directed extraction and purification of mango peels revealed the 5-(11'Z-heptadecenyl)-resorcinol (1) and the known 5(8'Z, 11'Z-heptadecadienyl)-resoreinol (2) previously not described in Mangifera indica L. The structures of both compounds were determined by extensive 1D and 2D NMR studies and MS. Both compounds exhibited potent cyclooxygenase (COX)-1 and COX-2 inhibitory activity with IC50 values ranging from 1.9 (2) to 3.5 mu M (1) and from 3.5 (2) to 4.4 (1) mu M, respectively, coming close to the IC50 values of reference drugs. 5-Lipoxygenase (5-LOX) catalyzed leukotriene formation was only slightly inhibited. Structure-activity studies by referring to synthetic saturated homologues indicated that the degree of unsaturation in the alkyl chain plays a key role for COX inhibitory activity, whereas the influence of chain length was less significant. (C) 2007 Elsevier Ltd. All rights reserved.
• Indonesian propolis: chemical composition, biological activity and botanical origin
  作者：Boryana Trusheva、Milena Popova、Eko Budi Koendhori、Iva Tsvetkova、Christo Naydenski、Vassya Bankova

  DOI：10.1080/14786419.2010.488235

  日期：2011.3

  From a biologically active extract of Indonesian propolis from East Java, 11 compounds were isolated and identified: four alk(en)ylresorcinols (obtained as an inseparable mixture) (1-4) were isolated for the first time from propolis, along with four prenylflavanones (6-9) and three cycloartane-type triterpenes (5, 10 and 11). The structures of the components were elucidated based on their spectral properties. All prenylflavanones demonstrated significant radical scavenging activity against diphenylpicrylhydrazyl radicals, and compound 6 showed significant antibacterial activity against Staphylococcus aureus. For the first time Macaranga tanarius L. and Mangifera indica L. are shown as plant sources of Indonesian propolis.
• 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.