trans-<3-(13)C>cinnamic acid | 850261-29-9

• 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: trans-<3-(13)C>cinnamic acid
• 英文别名: [7-(13)C]cinnamic acid；(E)-3-phenyl(313C)prop-2-enoic acid
• CAS: 850261-29-9
• 化学式: C₉H₈O₂
• 分子量: 149.15
• InChiKey: WBYWAXJHAXSJNI-WCJUTTSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trans-<3-(13)C>cinnamic acid 、 [2-13C]dihydrocinnamic acid 在 culture of roots of Anigozanthos pressii 作用下， 生成
  参考文献：
  名称：

  二氢肉桂酸参与 Anigozanthos preissii 苯酚的生物合成

  摘要：

  摘要 使用 Anigozanthos preissii 根培养物的饲养实验和 NMR 光谱研究揭示了苯丙烷和二氢苯丙烷之间的可逆相互转化，以及它们与苯菲酮的结合。多重标记的二氢肉桂酸转化为香豆酸，并进一步代谢为 2-羟基-9-(4-羟基苯基)-1H-phenalen-1-one（羟基茴香醚）。13 C NMR光谱和HPLC- 1 H NMR偶联被用于检测痕量的多重标记的生物合成中间体和进一步的代谢物。讨论了苯菲酮生物合成的途径。

  DOI：

  10.1016/s0031-9422(99)00116-8
• 作为产物：
  描述：

  苯甲酸-Alpha-13C 在 哌啶 、 吡啶 、 lithium aluminium tetrahydride 、 重铬酸吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 116.0h， 生成 trans-<3-(13)C>cinnamic acid
  参考文献：
  名称：

  Biosynthesis of the benzoyl moiety of cocaine from cinnamic acid via (R)-(+)-3-hydroxy-3-phenylpropanoic acid

  摘要：

  trans-[3-C-13,C-14]Cinnamic acid and the N-acetylcysteamine thioester of [3-C-13,C-14]-trans-cinnamic acid served as precursors of the benzoyl moiety of cocaine when fed to intact Erythroxylum coca plants. The specific incorporation of the thioester into the benzoyl carbonyl group of cocaine was established by means of C-13 NMR spectroscopy. (R)-(+)-[3-C-14]-3-hydroxy-3-phenylpropanoic acid was 11 times more effective than its (S)-(-)-isomer as a precursor of the benzoyl moiety of cocaine. A chemical degradation of the cocaine indicated that all the C-14 was located on its benzoyl moiety. Thus, the stereochemistry of the hydroxy group in 3-hydroxy-3-phenylpropanoic acid, is the same as that in the coenzyme A esters of 3-hydroxy fatty acids which are intermediates in the beta-oxidation of fatty acids.

  DOI：

  10.1016/s0031-9422(00)97546-0

文献信息

• Microwave-enhanced, solvent-free synthesis of singly and doubly13C-labelledtrans-cinnamic acid at the?- and?-carbon positions
  作者：Guibin Ma、Sophia E. Hayes

  DOI：10.1002/jlcr.878

  日期：2004.10.30

  13C-labelled trans-cinnamic acid (3-phenyl-2-propenoic acid) has been synthesized in one step using benzaldehyde-carbonyl-13C and malonic acid-2-13C in the presence of ammonium acetate under microwave irradiation and solvent-free conditions. Copyright © 2004 John Wiley & Sons, Ltd.

  在微波辐照和无溶剂条件下，使用苯甲醛-羰基-13C 和丙二酸-2-13C，在醋酸铵存在下一步合成了 13C 标记的反式肉桂酸（3-苯基-2-丙烯酸）。Copyright © 2004 John Wiley & Sons, Ltd. All Rights Reserved.
• Suzuki; Umezawa; Shimada, Journal of the Chemical Society. Perkin Transactions 1 (2001), 2001, # 24, p. 3252 - 3257
  作者：Suzuki、Umezawa、Shimada

  DOI：——

  日期：——
• Biosynthesis of the benzoyl moiety of cocaine from cinnamic acid via (R)-(+)-3-hydroxy-3-phenylpropanoic acid
  作者：Jeffrey A. Bjorklund、Edward Leete

  DOI：10.1016/s0031-9422(00)97546-0

  日期：1992.1

  trans-[3-C-13,C-14]Cinnamic acid and the N-acetylcysteamine thioester of [3-C-13,C-14]-trans-cinnamic acid served as precursors of the benzoyl moiety of cocaine when fed to intact Erythroxylum coca plants. The specific incorporation of the thioester into the benzoyl carbonyl group of cocaine was established by means of C-13 NMR spectroscopy. (R)-(+)-[3-C-14]-3-hydroxy-3-phenylpropanoic acid was 11 times more effective than its (S)-(-)-isomer as a precursor of the benzoyl moiety of cocaine. A chemical degradation of the cocaine indicated that all the C-14 was located on its benzoyl moiety. Thus, the stereochemistry of the hydroxy group in 3-hydroxy-3-phenylpropanoic acid, is the same as that in the coenzyme A esters of 3-hydroxy fatty acids which are intermediates in the beta-oxidation of fatty acids.
• Dihydrocinnamic acids are involved in the biosynthesis of phenylphenalenones in Anigozanthos preissii
  作者：Bettina Schmitt、Bernd Schneider

  DOI：10.1016/s0031-9422(99)00116-8

  日期：1999.9

  Abstract Feeding experiments using root cultures of Anigozanthos preissii and NMR spectroscopical studies revealed reversible interconversion between phenylpropanoids and dihydrophenylpropanoids, and their incorporation into phenylphenalenones. Multiply labelled dihydrocinnamic acid was transformed to coumaric acid and further metabolized to 2-hydroxy-9-(4-hydroxyphenyl)- 1H -phenalen-1-one (hydroxyanigorufone)

  摘要 使用 Anigozanthos preissii 根培养物的饲养实验和 NMR 光谱研究揭示了苯丙烷和二氢苯丙烷之间的可逆相互转化，以及它们与苯菲酮的结合。多重标记的二氢肉桂酸转化为香豆酸，并进一步代谢为 2-羟基-9-(4-羟基苯基)-1H-phenalen-1-one（羟基茴香醚）。13 C NMR光谱和HPLC- 1 H NMR偶联被用于检测痕量的多重标记的生物合成中间体和进一步的代谢物。讨论了苯菲酮生物合成的途径。