(-)-N-[4'-hydroxy-(E)-cinnamoyl]-3-hydroxy-L-tyrosine | 77201-64-0

• 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-[4'-hydroxy-(E)-cinnamoyl]-3-hydroxy-L-tyrosine
• 英文别名: p-coumaroyl-DOPA；N-Coumaroyl-3-hydroxytyrosine；(2S)-3-(3,4-dihydroxyphenyl)-2-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]amino]propanoic acid
• CAS: 77201-64-0
• 化学式: C₁₈H₁₇NO₆
• 分子量: 343.336
• InChiKey: UUXSHXGLOWJTDV-PXYYCUNGSA-N

物化性质

• 沸点：
  723.3±60.0 °C(Predicted)
• 密度：
  1.449±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  127
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  左旋多巴 在 氯化亚砜 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 70.75h， 生成 (-)-N-[4'-hydroxy-(E)-cinnamoyl]-3-hydroxy-L-tyrosine
  参考文献：
  名称：

  氯丁酰胺及其相关化合物抑制淀粉样蛋白β聚集的构效关系。

  摘要：

  阿尔茨海默氏病（AD）是一种神经退行性疾病，其特征是淀粉样β蛋白（Aβ）聚集。Aβ通过β折叠形成聚集，并诱导针对神经元细胞的细胞毒性。因此，天然存在的化合物抑制Aβ聚集是治疗AD的有前途的策略。我们已经报道了具有两个或多个邻苯二酚部分的咖啡酰奎尼酸和苯乙酮类糖苷强烈抑制了Aβ聚集。从可可豆（Theobroma cacao L.）分离的含有两个邻苯二酚部分的环丙酰胺（1）被认为对Aβ聚集具有预防作用。为了研究氯丁酰胺（1）抑制Aβ聚集的构效关系，我们通过1-DOPA，d-DOPA，l-酪氨酸，或l-苯丙氨酸和咖啡酸，对香豆酸或肉桂酸，化合物12和13衍生自1。在测试的化合物1-13中，含有一个或两个邻苯二酚部分的化合物表现出强的抗聚集活性，而非儿茶酚类相关化合物几乎没有活性。这表明至少一个儿茶酚部分对于抑制Aβ42聚集是必不可少的，并且该活性根据儿茶酚部分的数目而增加。因此，clovamid

  DOI：

  10.1016/j.bmc.2018.04.044

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
• PRODUCTS COMPRISING N-PHENYLPROPENOYL AMINO ACID AMIDES AND USES THEREOF
  申请人：Nestec S.A.

  公开号：EP2396083A2

  公开（公告）日：2011-12-21
• 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.
• [EN] PRODUCTS COMPRISING N-PHENYLPROPENOYL AMINO ACID AMIDES AND USES THEREOF<br/>[FR] PRODUITS COMPRENANT DES AMIDES D'ACIDE AMINÉ N-PHÉNYLPROPÉNOYLE ET UTILISATIONS DE CEUX-CI
  申请人：NESTEC SA

  公开号：WO2010091981A2

  公开（公告）日：2010-08-19

  The present invention relates to use of a composition comprising N-phenylpropenoyl amino acid amides for the preparation of a product to treat or prevent neurodegenerative disorders, cognitive decline, mild cognitive impairment, dementia, mood disorders, depression, sleep disorders, diseases involving protein aggregation in a human or animal, Alzheimer's disease, macular degeneration or diabetes. The invention further relates to products comprising N-phenylpropenoyl amino acid amides, including food and beverage products, food supplements, and pet food products, and methods for affecting cognitive performance of humans and animals.