3-没食子酰基奎宁酸 | 17365-11-6

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-没食子酰基奎宁酸
• 英文名称: (1R,2R,3R,5S)-5-carboxy-2,3,5-trihydroxycyclohexyl 3,4,5-trihydroxybenzoate
• 英文别名: 3‐O‐galloylquinic acid；3-O-galloyl quinic acid；3-O-galloyl-quinic acid；3-O-galloylquicnic acid；3-O-galloylquinic acid；5-O-galloylquinic acid；Theogallin；(1S,3R,4R,5R)-1,3,4-trihydroxy-5-(3,4,5-trihydroxybenzoyl)oxycyclohexane-1-carboxylic acid
• CAS: 17365-11-6
• 化学式: C₁₄H₁₆O₁₀
• 分子量: 344.275
• InChiKey: LDPLFHGGZNSKDS-FTBFGRRBSA-N

物化性质

• 沸点：
  754.4±60.0 °C(Predicted)
• 密度：
  1.85±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  185
• 氢给体数：
  7
• 氢受体数：
  10

安全信息

• WGK Germany：
  3

制备方法与用途

生物活性

Theogallin（3-单甘脂奎宁酸）是无咖啡因绿茶提取物中的活性成分，具有抗抑郁和增强认知的作用。

体内研究

Theogallin 能够显著降低大脑皮层活动。具体实验结果显示：

• 动物模型：6个月大的Fisher成年大鼠
• 剂量：20 mg/kg
• 给药方式：口服
• 结果：观察到对大脑皮层活动的抑制效果。

反应信息

• 作为反应物：
  描述：

  5-二异丙基氨基戊基胺 、 3-没食子酰基奎宁酸 在 1-羟基苯并三唑 、 三乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二甲基亚砜 为溶剂， 反应 0.02h， 生成
  参考文献：
  名称：

  Dynamic Profiling of Phenolic Acids during Pu-erh Tea Fermentation Using Derivatization Liquid Chromatography–Mass Spectrometry Approach

  摘要：

  Pu-erh tea, a famous traditional Chinese tea with multiple health benefits, is produced by microbial fermentation. It has been reported that major known bioactive compounds in green tea, e.g. epicatechin, epigallocatechin gallate, and theanine, decreased during fermentation. Then which components account for the benefits of Pu-erh tea? Phenolic acids are aromatic secondary metabolites and possess various biological properties. In this research, phenolic acids in Pu-erh tea were investigated qualitatively and quantitatively to reveal the influence of fermentation and their potential effects using 5-(diisopropylamino)amylamine (DIAAA) derivatization-ultrahigh performance liquid chromatography-quadrupole-time-of-flight/mass spectrometry (UHPLC-Q-TOF/MS) approach. A total of 33 phenolic acids were determined, and most of them were detected in Pu-erh tea for the first time. Moreover, gallic acid and theogallin were the major components in ripened and raw Pu-erh tea, respectively. Dynamic profiling revealed the increase of simple phenolic acids and the decrease of most of phenolic acid esters during Pu-erh tea fermentation. These results provided firm basis for practical fermentation and quality control of Pu-erh tea.

  DOI：

  10.1021/acs.jafc.9b00789

文献信息

• Tannins and Related Compounds. CXIV. Structures of Novel Fermentation Products, Theogallinin, Theaflavonin and Desgalloyl Theaflavonin from Black Tea, and Changes of Tea Leaf Polyphenols during Fermentation.
  作者：Fumio HASHIMOTO、Gen-ichiro NONAKA、Itsuo NISHIOKA

  DOI：10.1248/cpb.40.1383

  日期：——

  Continuing chemical examination of black tea has led to the isolation of three novel fermentation products, theogallinin (1), theaflavonin (10) and desgalloyl theaflavonin (11). The structure of 1 was established on the basis of physico-chemical evidence to be a condensation product linked through pyrogallol-pyrogallol rings in theogallin (2) and (-)-epigallocatechin 3-O-gallate (3), while 10 and 11 were characterized as B, B'-linked bisflavonoids formed by an oxidative coupling of isomyricitrin (12) and tea catechins [3 and (-)-epigallocatechin (4)]. Furthermore, high performance liquid chromatography analyses of the changes of tea polyphenols during fermentation have revealed that original tea catechins are more rapidly transformed by endogenous phenol oxidase to theasinensins (e.g.6, 8) and oolongtheanin (13) than the formerly known black tea pigments, theafiavins.

  在对红茶进行持续的化学检测中，成功分离出了三种新的发酵产物：茶黄素（1）、茶黄酮（10）和去没食子酰茶黄酮（11）。通过物理化学证据确定，1的结构是一种缩合产物，连接着邻苯三酚环和来自茶黄素（2）和（-）表没食子儿茶素3-O-没食子酸酯（3）的没食子酸环，而10和11则被鉴定为通过异鼠李素（12）和茶儿茶素[3和（-）表没食子儿茶素（4）]的氧化偶联形成的B，B'-连接的双黄酮。此外，高效液相色谱分析揭示了在发酵过程中，原始茶儿茶素被内源性酚氧化酶更快地转化为茶氨酸（例如6、8）和乌龙茶素（13），而非之前已知的红茶色素茶黄素。
• Physicochemical properties, antioxidant activities and comprehensive phenolic profiles of tea-macerated Chardonnay wine and model wine
  作者：Zijian Liang、Pangzhen Zhang、Wen Ma、Xin-An Zeng、Zhongxiang Fang

  DOI：10.1016/j.foodchem.2023.137748

  日期：2024.3
• STEVIOL GLYCOSIDE SOLUBILITY ENHANCERS
  申请人：CARGILL, INCORPORATED

  公开号：US20190223481A1

  公开（公告）日：2019-07-25

  A solubilized steviol glycoside composition including one or more steviol glycosides and one or more steviol glycoside solubility enhancers can be used as a sweetener composition to sweeten other compositions (sweetenable compositions) such as foods, beverages, medicines, oral hygiene compositions, pharmaceuticals, nutraceuticals, and the like.