(-)-(2R,3R)-5,7-dihydroxy-2-(3',4',5'-trihydroxy-phenyl)chroman-3-yl 3''-hydroxy-4'',5''-dimethoxybenzoate

• 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: (-)-(2R,3R)-5,7-dihydroxy-2-(3',4',5'-trihydroxy-phenyl)chroman-3-yl 3''-hydroxy-4'',5''-dimethoxybenzoate
• 英文别名: (-)-epigallocatechin-3-O-(3,4-O-dimethyl)gallate；EGCG3",4"diMe；[(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3-hydroxy-4,5-dimethoxybenzoate
• 化学式: C₂₄H₂₂O₁₁
• 分子量: 486.432
• InChiKey: URAFSMDJFKNRSI-IFMALSPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  175
• 氢给体数：
  6
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  3-benzyloxy-4,5-dimethoxybenzoyl chloride 在 palladium dihydroxide 4-二甲氨基吡啶 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (-)-(2R,3R)-5,7-dihydroxy-2-(3',4',5'-trihydroxy-phenyl)chroman-3-yl 3''-hydroxy-4'',5''-dimethoxybenzoate
  参考文献：
  名称：

  Regiospecific and enantioselective synthesis of methylated metabolites of tea catechins

  摘要：

  The regiospecific and enantioselective syntheses of various methylated regioisomers of epicatechin gallate (EGC) and epigallocatechin gallate (EGCG) have been achieved. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.04.010

文献信息

• Solid-Phase Synthesis of a Combinatorial Methylated (±)-Epigallocatechin Gallate Library and the Growth-Inhibitory Effects of these Compounds on Melanoma B16 Cells
  作者：Hiroshi Tanaka、Maasa Yamanouchi、Haruko Miyoshi、Keisuke Hirotsu、Hirofumi Tachibana、Takashi Takahashi

  DOI：10.1002/asia.201000372

  日期：——

  We report on the solid‐phase synthesis of a combinatorial methylated (±)‐epigallocatechin gallate (EGCG) library and its biological evaluation. Epigallocatechin gallate (EGCG) and its methylated derivatives, which are members of the catechin family, exhibit various anti‐cancer effects. The solid‐phase synthesis of methylated EGCG involves the preparation of the α‐acyloxyketone by the coupling of a

  我们报告了组合甲基化（±）-表没食子儿茶素没食子酸酯（EGCG）库的固相合成及其生物学评估。儿茶素家族的成员表没食子儿茶素没食子酸酯（EGCG）及其甲基化衍生物具有多种抗癌作用。甲基化EGCG的固相合成涉及通过固相负载的醛与酮和酸的偶联来制备α-酰氧基酮。固体负载的α-酰氧基酮的后续释放和还原醚化反应以良好的总收率提供了受保护的EGCG。成功制备了64种甲基化EGCG。还检查了甲基化EGCG文库的生长抑制作用。尽管EGCG的甲基化通常会导致生长抑制作用降低，7-OMe EGCG的生长抑制作用与EGCG相当。7-OMe EGCG由于具有更高的生物利用度，因此是有吸引力的候选药物。
• Relationship between the Biological Activities of Methylated Derivatives of (−)-Epigallocatechin-3-<i>O</i>-gallate (EGCG) and Their Cell Surface Binding Activities
  作者：Satomi Yano、Yoshinori Fujimura、Daisuke Umeda、Toshio Miyase、Koji Yamada、Hirofumi Tachibana

  DOI：10.1021/jf071176o

  日期：2007.8.1

  It was previously reported that (-)-epigallocatechin-3-O-gallate (EGCG) suppresses the expression of the high-affinity IgE receptor Fc epsilon RI in human basophilic cells and that this suppressive effect is associated with EGCG binding to the cell surface. This study examined the effects of five methylated derivatives of EGCG, (-)-epigallocatechin-3-O-(3-O-methyl)gallate (EGCG 3 '' Me), (-)-epigallocatechin-3-O-(4-O-methyl)gallate (EGCG 4 '' Me), (-)-4'-O-methyl-epigallocatechin-3-O-gallate (EGCG 4'Me), (-)-epigallocatechin-3-O-(3,4-O-methyl)gallate (EGCG 3 '' 4 '' diMe), and (-)-4'-O-methyl-epigallocatechin-3-O-(4-O-methyl)gallate (EGCG 4'4 '' diMe) on Fc epsilon RI expression and ERK1/2 phosphorylation, and each of their cell surface binding activities was measured. Of these five methylated derivatives, three that are methylated at the 3 ''- and/or 4 ''-position, EGCG 3 '' Me, EGCG 4 '' Me, and EGCG 3 '' 4 '' diMe, suppressed Fc epsilon RI expression and ERK1/2 phosphorylation, although the suppressive effects were lower than that of EGCG. EGCG 4'Me and EGCG 4'4 '' diMe, both of which are methylated at the 4'-position, did not demonstrate a suppressive effect. Furthermore, it was found that EGCG 3 '' Me, EGCG 4 '' Me, EGCG 3 '' 4 '' diMe, and EGCG 4'Me, which are methylated at the 3 ''- and/or 4 ''-positions or the 4'-position, could bind to the cell surface even though their binding activities were lower than that of EGCG. Only EGCG 4'4 '' diMe, which is methylated at both the 4'- and 4 ''-positions, could not bind. These results suggest that the trihydroxyl structure of the B ring is essential for EGCG to exert the suppressive effects and that the hydroxyl groups on both the 4'-position in the B ring and the 4 ''-position in the gallate are crucial for the cell surface binding activity of EGCG.