catechin hydrate | 154-23-4

• 物质功能分类: 生物化工 - 天然产物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: catechin hydrate
• 英文别名: catechin；(3S)-2-(3,4-dihydroxyphenyl)chromane-3,5,7-triol；(3S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
• CAS: 154-23-4；490-46-0；7295-85-4；13392-26-2；17334-50-8；18829-70-4；35323-91-2；72690-97-2
• 化学式: C₁₅H₁₄O₆
• 分子量: 290.273
• InChiKey: PFTAWBLQPZVEMU-CFMCSPIPSA-N

物化性质

• 熔点：
  175-177 °C (anhydrous)(lit.)
• 比旋光度：
  D18 +16 to +18.4°
• 沸点：
  352.36°C (rough estimate)
• 密度：
  1.2451 (rough estimate)
• 溶解度：
  DMSO（微溶）、甲醇（微溶）、水（微溶、超声处理、加热）
• LogP：
  0.510

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  110
• 氢给体数：
  5
• 氢受体数：
  6

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2932999099
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

制备方法与用途

性状

儿茶素为无色结晶形固体，能溶于水，熔点在212～216℃之间。微溶于冷水和乙醚，可溶于热水、乙醇、冰醋酸和丙酮，不溶于苯、氯仿和石油醚。

概述

茶叶中含有丰富的儿茶素类物质，占茶叶干重的12%至24%，是茶叶中最具生理活性和保健功效的成分。主要种类包括表儿茶素（EC）、表没食子儿茶素（EGC）、表儿茶素没食子酸酯（ECG）和表没食子儿茶素没食子酸酯（EGCG）。此外，还含有少量的(+)一GC、GCG、CG和(+)一C。在这些物质中，EGCG和ECG为主要组分，分别占儿茶素总量的50%和15%左右。

用途

儿茶素是一种天然抗氧化剂，存在于绿茶、苹果、葡萄、红酒和可可等食物中。研究表明，它具有多种药理作用：

• 清除自由基：作为天然油脂抗氧化剂，其抗氧化活性甚至比维生素E高，能够清除人体产生的自由基，保护细胞免受氧化损伤。
• 预防心血管疾病和癌症等多种功能。

生产方法

采用蔷薇科悬钩子属植物茅莓（Rubus parvifollus L）全株干燥粉末，用乙醇回流多次提取后回收乙醇。残渣用水去除脂溶性成分，再悬浮于水中并用乙酸乙酯萃取，萃取物溶于甲醇中拌硅胶过层析柱，以石油醚：乙酸乙酯梯度洗脱，分得淡黄色针状结晶成分，即为(+)-儿茶素。

化学性质

儿茶素来源于茶叶中的有效成分，在水溶液中易被空气氧化。常用作抗氧化剂。右旋儿茶精还有降低毛细血管通透性、止泻、止血、抗病毒、杀真菌、抑制ACE及预防胃溃疡等多种作用。

类别与储存

• 类别：有毒物品
• 毒性分级：低毒
• 急性毒性：腹腔大鼠LD50: 1084毫克/公斤；腹腔小鼠LD50: 1000毫克/公斤
• 可燃性危险特性：热分解，产生辛辣刺激烟雾
• 储运特性：库房低温通风干燥

灭火剂

水、二氧化碳、泡沫、干粉。

反应信息

• 作为反应物：
  描述：

  catechin hydrate 在 azide radical 作用下， 以 水 为溶剂， 生成
  参考文献：
  名称：

  Antioxidant Potential of Gallocatechins. A Pulse Radiolysis and Laser Photolysis Study

  摘要：

  Gallocatechins and catechins, which are constituents of green tea, and related, simpler single-ring model compounds undergo one-electron oxidation by the azidyl radical (k = (1.4-4.8) x 10(9) M(-1) s(-1)), which was used as a model one-electron, rapid oxidant. The initial oxidation leads to the formation of a mixture of A- and B- (or C-) ring phenoxyl radicals. This finding was confirmed by comparison with the spectra of 3,5-dihydroxyanisole (the model for A ring) and methyl gallate (the model for B or C ring) radicals and by photoionization experiments in which only the B-ring radical of epigallocatechin was generated, as expected from its lower ionization potential. The A-ring phenoxyl radical is converted to the B- (or C-) ring phenoxyl radical by inter- and intramolecular electron and proton transfer. The activation parameters clearly indicate solvent-assisted intermolecular electron and proton transfer, whereas intramolecular transfer in epigallocatechin gallate radicals is suggested to proceed through an intermediate molecular complex formation. Acid-base equilibria of parent gallocatechins (pK(al) > 8.0) are significantly altered in the corresponding phenoxyl radicals (pK(rl) = 4.4-5.5). The low reduction potentials of gallocatechin radicals, E(7) = 0.42 V (which is lower than that of vitamin E radicals, E(7) = 0.48 V), are responsible for their antioxidant efficacy, which may include the repair of vitamin E radicals. These low reduction potentials also imply high susceptibility of parent gallocatechins to rapid oxidation in aerated aqueous media. The reactivity of epigallocatechin gallate with superoxide radical at pH 7, k = 7.3 x 10(5) M(-1) s(-1) is one of the highest measured rates of reduction of superoxide radical by any chemical antioxidant. In this reaction, superoxide is converted to hydrogen peroxide, thus eliminating the redox cycling that may be involved in the corresponding oxidation reaction. The high rates of quenching of singlet oxygen by gallocatechins in acetonitrile, k = (1.1-2.2) x 10(8) M(-1) s(-1), are comparable to quenching by vitamin E, k = 5 x 10(8) M(-1) s(-1).

  DOI：

  10.1021/ja00144a014

文献信息

• NOVEL ANALOGUES OF EPICATECHIN AND RELATED POLYPHENOLS
  申请人：SPHAERA PHARMA PVT. LTD.

  公开号：US20160039781A1

  公开（公告）日：2016-02-11

  The present invention provides novel analogues of epicatechin and related polyphenols, their variously functionalized derivatives, process for preparation of the same, composition comprising these compounds and their method of use.

  本发明提供了表儿茶素及相关多酚的新颖类似物，它们的各种官能化衍生物，以及它们的制备方法、包含这些化合物的组合物和它们的使用方法。
• MOLECULARLY IMPRINTED POLYMERS
  申请人：Hearn Milton T. W.

  公开号：US20120052757A1

  公开（公告）日：2012-03-01

  The present invention provides methods of designing molecularly imprinted polymers (MIPs) which have applications in extracting bioactive compounds from a range of bioprocessing feedstocks and wastes. The present invention is further directed to MIPs designed by the methods of the present invention.

  本发明提供了设计分子印迹聚合物（MIPs）的方法，这些方法在从各种生物加工原料和废弃物中提取生物活性化合物方面具有应用。本发明进一步针对由本发明方法设计的MIPs。
• Assays, methods and means
  申请人：Maxwell Patrick Henry

  公开号：US20100272726A1

  公开（公告）日：2010-10-28

  A novel class of hydroxylases is described having the amino acid sequence of SEQ ID NO: 2, 4, 6 and 8, and variants and fragments thereof having HIF hydroxylation activity. The polypeptides of the invention have in particular prolyl hydroxylase activity. An assay method monitors the interaction of the HIF hydroxylase with a substrate. Modulators of HIF hydroxylase are provided for use in the treatment of a condition associated with increased or decreased HIF levels or activity or for the treatment of a condition where it is desirable to modulate HIF levels or activity.

  本文描述了一种新型的羟化酶，其氨基酸序列为SEQ ID NO：2、4、6和8，以及具有HIF羟化活性的变体和片段。本发明的多肽特别具有脯氨酸羟化酶活性。一种测定方法监测HIF羟化酶与底物的相互作用。提供了HIF羟化酶的调节剂，用于治疗与HIF水平或活性增加或减少相关的疾病，或用于治疗需要调节HIF水平或活性的疾病。
• Assays, Methods and Means
  申请人：Isis Innovation Limited

  公开号：US20140294842A1

  公开（公告）日：2014-10-02

  A novel class of hydroxylases is described having the amino acid sequence of SEQ ID No. 2, 4, 6 and 8, and variants and fragments thereof having HIF hydroxylation activity. The polypeptides of the invention have in particular prolyl hydroxylase activity. An assay method monitors the interaction of the HIF hydroxylase with a substrate. Modulators of HIF hydroxylase are provided for use in the treatment of a condition associated with increased or decreased HIF levels or activity or for the treatment of a condition where it is desirable to modulate HIF levels or activity.

  本文介绍了一类新型羟化酶，其氨基酸序列为SEQ ID No. 2、4、6和8及其变异体和片段，具有HIF羟化活性。本发明的多肽特别具有脯氨酸羟化酶活性。一种检测方法监测HIF羟化酶与底物的相互作用。提供用于治疗与HIF水平或活性增加或减少有关的疾病或治疗需要调节HIF水平或活性的疾病的HIF羟化酶调节剂。
• ASSAYS, METHODS AND MEANS
  申请人：ISIS INNOVATION LIMITED

  公开号：US20160097078A1

  公开（公告）日：2016-04-07

  A novel class of hydroxylases is described having the amino acid sequence of SEQ ID NO: 2, 4, 6 and 8, and variants and fragments thereof having HIF hydroxylation activity. The polypeptides of the invention have in particular prolyl hydroxylase activity. An assay method monitors the interaction of the HIF hydroxylase with a substrate. Modulators of HIF hydroxylase are provided for use in the treatment of a condition associated with increased or decreased HIF levels or activity or for the treatment of a condition where it is desirable to modulate HIF levels or activity.

  本文描述了一种新型羟化酶，其具有SEQ ID NO: 2、4、6和8的氨基酸序列，以及具有HIF羟化活性的变体和片段。发明的多肽具有特别的脯氨酸羟化酶活性。一种检测方法监测HIF羟化酶与底物的相互作用。提供了HIF羟化酶调节剂，用于治疗与HIF水平或活性增加或减少相关的疾病，或用于治疗需要调节HIF水平或活性的疾病。