(-)-epigallocatechin (2α,3α) | 136892-45-0

• 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: (-)-epigallocatechin (2α,3α)
• 英文别名: (+)-epigallocatechin；(-)-epigallocatechin；epigallocatechin；epigallocatechol；gallocatechin；(2S,3S)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
• CAS: 136892-45-0
• 化学式: C₁₅H₁₄O₇
• 分子量: 306.272
• InChiKey: XMOCLSLCDHWDHP-WFASDCNBSA-N

物化性质

• 熔点：
  217-219 °C
• 沸点：
  685.6±55.0 °C(Predicted)
• 密度：
  1.695±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  22
• 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：
  131
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (-)-epigallocatechin (2α,3α) 生成 (2S,3S)-2-(3,4,5-trihydroxyphenyl)-8-[[(2S,3S)-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-8-yl]methyl]-3,4-dihydro-2H-chromene-3,5,7-triol
  参考文献：
  名称：

  HASHIMOTO, FUMIO;NONAKA, GEN-ICHIRO;NISHIOKA, ITSUO, CHEM. AND PHARM. BULL., 37,(1989) N2, C. 3255-3263

  摘要：

  DOI：
• 作为产物：
  描述：

  (-)-表没食子儿茶素没食子酸酯 在 柠檬酸 作用下， 以 aq. phosphate buffer 为溶剂， 反应 4.0h， 以95%的产率得到(-)-epigallocatechin (2α,3α)
  参考文献：
  名称：

  Enhancement of Antioxidant Activity in O/W Emulsion and Cholesterol-Reducing Capacity of Epigallocatechin by Derivatization with Representative Phytosterols

  摘要：

  In this study, derivatization of epigallocatechin (EGC) by representative phytosterols (stigmasterol and beta-sitosterol) was performed employing Steglich esterification. The structural identity and purity of epigallocatechin beta-sitosterol (ESi) and epigallocatechin stigmasterol (ESt) were confirmed by NMR, FT-IR, and HPLC-MS. Further evaluation of ESi and ESt revealed their extraordinary antioxidant activities in O/W emulsion. Two different radical sources in oil or aqueous phase were applied to explore the antioxidant behavior in O/W emulsion. The mechanism was further investigated by fluorescent microscopy and transmission electron microscopy (TEM). Furthermore, incorporation of EGC with stigmasterol and beta-sitosterol notably enhanced the cholesterol-reducing activity. TEM studies suggested the hydrogen bonding of EGC strengthened the aggregation network of ESi and ESt in the bile salt micelle. The exceptional properties of ESi and ESt signified their intriguing utilization in the food industry.

  DOI：

  10.1021/acs.jafc.9b04382

文献信息

• METHODS OF TREATING COGNITIVE AND BEHAVIORAL IMPAIRMENT IN DOWN SYNDROME AND ALZHEIMERS DISEASE PATIENTS
  申请人：AVANTI BIOSCIENCES, INC.

  公开号：US20180000774A1

  公开（公告）日：2018-01-04

  The present invention relates to methods of treating cognitive and behavioral impairment in Down syndrome and/or Alzheimer's disease patients, Alzheimer's disease, neurodegenerative disease, cancer, DYRK1A-mediated disorders and methods of modulating and inhibiting DYRK1-A comprising use of catechins.

  本发明涉及治疗唐氏综合症和/或阿尔茨海默病患者认知和行为障碍的方法，阿尔茨海默病，神经退行性疾病，癌症，DYRK1A介导的疾病以及使用儿茶素调节和抑制DYRK1-A的方法。
• Cytotoxicity of plant flavonoids against HeLa cells
  作者：Akihisa Mori、Chikao Nishino、Nobuyasu Enoki、Shinkichi Tawata

  DOI：10.1016/0031-9422(88)80264-4

  日期：——

  Abstract (-)-Epigallocatechin and 28 other plant flavonoids were tested for cytotoxic activity against HeLa cells. Flavones and flavanones were active and several compounds with planar and non-planar ring systems showed high cytotoxic activities. Although no clear structure activity relationship was deduced, hydroxyl groups on the A- and B- ring affected the cytotoxic potency positively or negatively, depending

  摘要 (-)-表没食子儿茶素和其他 28 种植物黄酮类化合物对 HeLa 细胞的细胞毒活性进行了测试。黄酮和黄烷酮具有活性，几种具有平面和非平面环系统的化合物显示出高细胞毒活性。虽然没有推断出明确的结构活性关系，但 A- 和 B- 环上的羟基对细胞毒性效力产生正面或负面影响，具体取决于取代位置。胸苷的摄取主要受杨梅素的抑制，而尿苷的摄取受(-)-表没食子儿茶素的抑制；7,8-二羟基黄酮抑制胸苷和尿苷的摄取。
• HASHIMOTO, FUMIO;NONAKA, GEN-ICHIRO;NISHIOKA, ITSUO, CHEM. AND PHARM. BULL., 37,(1989) N2, C. 3255-3263
  作者：HASHIMOTO, FUMIO、NONAKA, GEN-ICHIRO、NISHIOKA, ITSUO

  DOI：——

  日期：——
• COMPOUNDS AND METHODS FOR TREATING PAIN
  申请人：Akron Molecules GmbH

  公开号：EP2637649A2

  公开（公告）日：2013-09-18
• Anti-Arrhythmia Agents, Methods of Their Use, Methods of Their Identification and Kits Therefore
  申请人：Wolkowicz Paul

  公开号：US20110144125A1

  公开（公告）日：2011-06-16

  The disclosure describes an animal model for simulating cardiac arrhythmia. Methods of discovering new anti-arrhythmia drugs using the model are described. Novel anti-arrhythmia agents are provided, as are pharmaceutical compositions made from the agents. Methods of inhibiting spontaneous mechanical activity in myocardially-derived biological systems, and methods of treating and preventing cardiac arrhythmia based on novel anti-arrhythmia agents are described. Kits for performing the above methods are also described.