(8'Z)-5-(heptadeca-8'-enyl)benzene-1,3-diol | 52483-19-9

• 物质功能分类: 天然产物 - 酚类
• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (8'Z)-5-(heptadeca-8'-enyl)benzene-1,3-diol
• 英文别名: 1,3-dihydroxy-5-heptadec-cis-8'-enylbenzene；5-(8′Z-heptadecenyl)-resorcinol；5-(8'Z-heptadecenyl)resorcinol；5-(8Z-heptadecenyl)resorcinol；5-(Z-heptadec-8-enyl) resorcinol；5-[(Z)-heptadec-8-enyl]benzene-1,3-diol
• CAS: 52483-19-9
• 化学式: C₂₃H₃₈O₂
• 分子量: 346.554
• InChiKey: DQSWQRFGZIJUCI-KTKRTIGZSA-N

物化性质

• 沸点：
  494.4±25.0 °C(Predicted)
• 密度：
  0.961±0.06 g/cm3(Predicted)

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

安全信息

• 海关编码：
  2907299090
• 储存条件：
  存放在2-8℃环境中，需要干燥并密闭保存。

制备方法与用途

5-庚二酸-顺-8-烯基间苯二酚是从黄化水稻幼苗中分离出的一种5-烷基间苯二酚，它不仅具有抗稻瘟病真菌的作用，还能介导DNA的松弛作用。

反应信息

• 作为反应物：
  描述：

  (8'Z)-5-(heptadeca-8'-enyl)benzene-1,3-diol 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

• Bioassay-Guided Isolation and Structural Modification of the Anti-TB Resorcinols from<i>Ardisia gigantifolia</i>
  作者：Yi-Fu Guan、Xun Song、Ming-Hua Qiu、Shi-Hong Luo、Bao-Jie Wang、Nguyen Van Hung、Nguyen M. Cuong、Djaja Doel Soejarto、Harry H.S. Fong、Scott G. Franzblau、Sheng-Hong Li、Zhen-Dan He、Hong-Jie Zhang

  DOI：10.1111/cbdd.12756

  日期：2016.8

  Tuberculosis (TB) is a highly contagious disease mainly caused by Mycobacterium tuberculosis H37 RV . Antitubercular (anti-TB) bioassay-guided isolation of the CHCl3 extract of the leaves and stems of the medicinal plant Ardisia gigantifolia led to the isolation of two anti-TB 5-alkylresorcinols, 5-(8Z-heptadecenyl) resorcinol (1) and 5-(8Z-pentadecenyl) resorcinol (2). We further synthesized 15 derivatives

  结核病（TB）是一种高度传染性疾病，主要由结核分枝杆菌H37 RV引起。抗结核（抗TB）生物测定指导的药用植物Ardisia gigantifolia叶片和茎的CHCl3提取物的分离导致分离出两种抗结核的5-烷基间苯二酚，5-（8Z-庚烯基）间苯二酚（1）和5-（8Z-十五烯基）间苯二酚（2）。我们基于这两种天然产物进一步合成了15种衍生物。评估了这些化合物（天然和合成）对结核分枝杆菌H37 RV的抗TB活性。间苯二酚1和2具有抗TB活性，在MABA分析中的MIC值分别为34.4μM和79.2μM，在LORA分析中的MIC值分别为91.7μM和168.3μM。在这些衍生品中，发现化合物8显示出比其合成前体（2）更高的抗TB活性，在MABA测定中MIC值为42.0μM，在LORA测定中MIC值为100.2μM。应将活性化合物视为一类新型的抗结核病药物，作为进一步研究的新热点。基于这些衍生物阐
• Structure elucidation of naturally occurring long-chain mono- and dienes
  作者：John R. Barr、Ralph T. Scannell、Keiichi Yamaguchi

  DOI：10.1021/jo00263a046

  日期：1989.1
• BARR, JOHN R.;SCANNELL, RALPH T.;YAMAGUCHI, KEIICHI, J. ORG. CHEM., 54,(1989) N, C. 494-496
  作者：BARR, JOHN R.、SCANNELL, RALPH T.、YAMAGUCHI, KEIICHI

  DOI：——

  日期：——
• 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.