(+)-N-(E)-cinnamoyl-L-aspartic acid | 860295-30-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (+)-N-(E)-cinnamoyl-L-aspartic acid
• 英文别名: 2-((2E)-3-Phenylprop-2-enamido)butanedioic acid, (2S)-；(2S)-2-[[(E)-3-phenylprop-2-enoyl]amino]butanedioic acid
• CAS: 860295-30-3
• 化学式: C₁₃H₁₃NO₅
• 分子量: 263.25
• InChiKey: DAHASNDSDHUIRW-FGEFZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  肉桂酸 在 水 、 三乙胺 、 sodium hydroxide 作用下， 以 乙腈 为溶剂， 反应 24.55h， 生成 (+)-N-(E)-cinnamoyl-L-aspartic acid
  参考文献：
  名称：

  Colon-Targeted Trans-Cinnamic Acid Ameliorates Rat Colitis by Activating GPR109A

  摘要：

  我们设计了结肠靶向反式肉桂酸（tCA），并合成了其与谷氨酸（tCA-GA）和天冬氨酸（tCA-AA）的共轭物。我们使用二硝基苯磺酸诱导的大鼠结肠炎模型评估了结肠靶向 tCA 的抗结肠炎活性。共轭物降低了三氯乙酸的分布系数和 Caco-2 细胞的渗透性，并在盲肠中转化为三氯乙酸，tCA-GA 的转化率和转化百分比均高于 tCA-AA。口服后，tCA-GA 向盲肠输送的三氯乙酸量更高，与目前治疗炎症性肠病的三氯乙酸和柳氮磺胺吡啶（SSZ）相比，具有更好的抗结肠炎效果。在细胞试验中，三氯乙酸是 GPR109A 的完全激动剂（EC50：530 µM）。同时服用 GPR109A 拮抗剂 mepenzolate 会显著削弱 tCA-GA 的抗结肠炎作用。总之，结肠靶向三氯乙酸通过有效激活发炎结肠中的 GPR109A，增强了三氯乙酸的抗结肠炎活性，使三氯乙酸的治疗效果优于 SSZ。

  DOI：

  10.3390/pharmaceutics15010041

文献信息

• Isolation, Structure Determination, Synthesis, and Sensory Activity of <i>N</i>-Phenylpropenoyl-<scp>l</scp>-amino Acids from Cocoa (<i>Theobroma cacao</i>)
  作者：Timo Stark、Thomas Hofmann

  DOI：10.1021/jf050458q

  日期：2005.6.1

  Application of chromatographic separation and taste dilution analyses recently revealed besides procyanidins a series of N-phenylpropenoyl amino acids as the key contributors to the astringent taste of nonfermented cocoa beans as well as roasted cocoa nibs. Because these amides have as yet not been reported as key taste compounds, this paper presents the isolation, structure determination, and sensory activity of these amino acid amides. Besides the previously reported (-)-N-[3',4'-dihydroxy-(E)-cinnamoyl]-3-hydroxy-L-tyrosine (clovamide), (-)-N-[4'-hydroxy-(E)-cinnamoyl]-L-tyrosine (deoxyclovamide), and (-)-N-[3',4'-dihydroxy-(E)-cinnamoyl]-L-tyrosine, seven additional amides, namely, (+)-N-[3',4'-dihydroxy-(E)-cinnamoyl]-L-aspartic acid, (+)-N-[4'-hydroxy-(E)-cinnamoyl]-L-aspartic acid, (-)-N-[3',4'-dihydroxy-(E)-cinnamoyl]-L-glutamic acid, (-)-N-[4'-hydroxy-(E)-cinnamoyl]-L-glutamic acid, (-)-N-[4'-hydroxy-(E)-cinnamoyl]-3-hydroxy-L-tyrosine, (+)-N-[4'-hydroxy-3'-methoxy-(E)-cinnamoyl]-L-aspartic acid, and (+)-N-[(E)-cinnamoyl]-L-aspartic acid, were identified for the first time in cocoa products by means of LC-MS/MS, 1D/2D-NMR, UV-vis, CID spectroscopy, and polarimetry, as well as independent enantiopure synthesis. Using the recently developed half-tongue test, human recognition thresholds for the astringent and mouth-drying oral sensation were determined to be between 26 and 220 mu mol/L (water) depending on the amino acid moiety. In addition, exposure to light rapidly converted these [E]-configured N-phenylpropenoyl amino acids into the corresponding [2]-isomers, thus indicating that analysis of these compounds in food and plant materials needs to be performed very carefully in the absence of light to prevent artifact formation.
• MEDIZINISCHE VERWENDUNG VON N-PHENYLPROPENOYL-AMINOSÄUREDERIVATEN
  申请人：Westfälische Wilhelms-Universität Münster

  公开号：EP2040692B1

  公开（公告）日：2012-09-19
• Medical Use of N-Phenylpropenoyl-Amino Acid Derivatives and Related Compounds
  申请人：Hensel Andreas

  公开号：US20100008976A1

  公开（公告）日：2010-01-14

  The invention relates to compounds having the general structural formula (formula I) for use in a diagnostic method or a method for treatment of the human or animal body by surgery or therapy.