ent-catechin 3',4',5,7-tetra-O-methyl ether | 104263-86-7

• 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: ent-catechin 3',4',5,7-tetra-O-methyl ether
• 英文别名: 3',4',5,7-tetra-O-methyl-ent-catechin；tetra-O-methyl-(-)-epicatechin；((-)-catechol)-tetramethyl ether；((-)-Catechin)-tetramethylaether；2-(3,4-Dimethoxyphenyl)-5,7-dimethoxy-3-chromanol；(2S,3R)-2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-3,4-dihydro-2H-chromen-3-ol
• CAS: 104263-86-7
• 化学式: C₁₉H₂₂O₆
• 分子量: 346.38
• InChiKey: GKPNPQODFXMCGO-KUHUBIRLSA-N

物化性质

• 熔点：
  144-145 °C(Solv: ethanol (64-17-5))
• 沸点：
  517.7±50.0 °C(Predicted)
• 密度：
  1.217±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  在 sodium cyanoborohydride 、 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 49.5h， 生成 ent-catechin 3',4',5,7-tetra-O-methyl ether
  参考文献：
  名称：

  A-type proanthocyanidins from peanut skins

  摘要：

  Six A-type proanthocyanidins were isolated from the water-soluble fraction of peanut skins. On the basis of spectral data, reductive cleavage with sodium cyanoborohydride, and chiral HPLC analysis, three new compounds, epicatechin-(2 beta-->O-->7, 4 beta --> 6)-catechin, epicatechin-(2 beta --> O --> 7, 4 beta --> 6)-ent-catechin and epicatechin-(2 beta --> O --> 7, 4 beta --> 6)-ent-epicatechin were unambiguously identified, together with the three known compounds, psoanthocyanidin A-1, proanthocyanidin A-2 and epicatechin-(2 beta-->O-->7, 4 beta-->8)-ent-epicatechin. (13)C NMR chemical shift rules to distinguish between [2-->O-->7, 4-->8] and [2-->O -->7,4-->6] double-linked heptamethyl ethers of A-type proanthocyanidins are proposed. Bioassay experiments showed that these six compounds possess substantial activity against hyaluronidase. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(98)00736-5

文献信息

• Yang, Shen-Chyun; Fang, Jim-Min; Cheng, Yu-Shia, Journal of the Chinese Chemical Society, 1995, vol. 42, # 3, p. 573 - 578
  作者：Yang, Shen-Chyun、Fang, Jim-Min、Cheng, Yu-Shia

  DOI：——

  日期：——
• Freudenberg; Purrmann, Chemische Berichte, 1923, vol. 56, p. 1189
  作者：Freudenberg、Purrmann

  DOI：——

  日期：——
• BROWN, B. R.;FULLER, M. J., J. CHEM. RES. SYNOP., 1986, N 4, 140-141
  作者：BROWN, B. R.、FULLER, M. J.

  DOI：——

  日期：——
• A-type proanthocyanidins from peanut skins
  作者：H Lou

  DOI：10.1016/s0031-9422(98)00736-5

  日期：1999.5

  Six A-type proanthocyanidins were isolated from the water-soluble fraction of peanut skins. On the basis of spectral data, reductive cleavage with sodium cyanoborohydride, and chiral HPLC analysis, three new compounds, epicatechin-(2 beta-->O-->7, 4 beta --> 6)-catechin, epicatechin-(2 beta --> O --> 7, 4 beta --> 6)-ent-catechin and epicatechin-(2 beta --> O --> 7, 4 beta --> 6)-ent-epicatechin were unambiguously identified, together with the three known compounds, psoanthocyanidin A-1, proanthocyanidin A-2 and epicatechin-(2 beta-->O-->7, 4 beta-->8)-ent-epicatechin. (13)C NMR chemical shift rules to distinguish between [2-->O-->7, 4-->8] and [2-->O -->7,4-->6] double-linked heptamethyl ethers of A-type proanthocyanidins are proposed. Bioassay experiments showed that these six compounds possess substantial activity against hyaluronidase. (C) 1999 Elsevier Science Ltd. All rights reserved.