[2-13C,4'-O13CH3]4-methoxycinnamic acid | 1353643-95-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: [2-13C,4'-O13CH3]4-methoxycinnamic acid
• 英文别名: [2-¹³C,4'-O¹³CH3]4-methoxycinnamic acid
• CAS: 1353643-95-4
• 化学式: C₁₀H₁₀O₃
• 分子量: 180.166
• InChiKey: AFDXODALSZRGIH-SPBYTNOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.79
• 重原子数：
  13.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  [2-(13)C]4'-[methoxy-(13)C]cinnamic acid [methyl-(13)C] ester 在 水 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 2.0h， 生成 [2-13C,4'-O13CH3]4-methoxycinnamic acid
  参考文献：
  名称：

  O-Methylation of phenylphenalenone phytoalexins in Musa acuminata and Wachendorfia thyrsiflora

  摘要：

  Biosynthetic O-methylation at various sites along the backbone of inducible phenylphenalenones in Musa acuminata var. "Williams" (Musaceae) and Wachendorfia thyrsiflora (Haemodoraceae) was investigated using C-13-labelled precursors. The inducibility of O-methylated metabolites was demonstrated in both species and the origin of methoxyl group from [methyl-C-13](L)-methionine was confirmed. In addition to known phenylphenalenones, a methoxylated metabolite, 4-(4-hydroxy-3-methoxy-phenyl)-benzo[de]isochromene-1,3-dione, was detected and its structure elucidated mainly by NMR spectroscopic techniques. The experiments were used to discriminate methionine-derived and artificial methoxy groups formed during methanolic extraction. Finally, demethylation of 4'-methoxycinnamic acid and subsequent conversion to 3',4'-methylenedioxycinnamic acid was demonstrated in M. acuminata. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2009.10.019

文献信息

• 4-Methoxycinnamic acid – An unusual phenylpropanoid involved in phenylphenalenone biosynthesis in Anigozanthos preissii
  作者：William Hidalgo、Marco Kai、Bernd Schneider

  DOI：10.1016/j.phytochem.2015.07.017

  日期：2015.9

  precursor-product relationships between phenylpropanoids and phenylphenalenones whose phenyl rings share identical substitution patterns. Four phenylpropanoic acids, including ferulic acid and the unusual 4-methoxycinnamic acid, were used in (13)C-labeled form as substrates to study their incorporation into phenylphenalenones. In addition to the previously reported 2-hydroxy-9-(4'-hydroxy-3'-methoxyphenyl)-1H-phenalen-1-one

  Anigozanthos preissii 和 Wachendorfia thyrsiflora (Haemodoraceae) 的体外根培养是研究苯菲酮生物合成的合适生物系统。在这里，我们报告了我们如何使用这些根培养物来研究苯丙烷类化合物和苯萘酮之间的前体-产物关系，其苯环具有相同的取代模式。四种苯丙酸，包括阿魏酸和不寻常的 4-甲氧基肉桂酸，以 (13) C 标记的形式用作底物来研究它们与苯菲酮的结合。除了之前报道的2-羟基-9-(4'-羟基-3'-甲氧基苯基)-1H-phenalen-1-one(俗名musanolone F)，2-羟基-9-(4'-甲氧基苯基) -1H-phenalen-1-one（提议的俗名 4'-甲氧基anigorufone）被发现是 A. preissii 中的一种生物合成产物。4'-甲氧基肉桂酸的碳骨架作为一个完整的单元在生物合成中引入，包括其侧苯环上的 4
• Publisher's Note
  作者：Hidalgo, William、Kai, Marco、Schneider, Bernd

  DOI：10.1016/j.phytochem.2015.05.017

  日期：2015.9