5,3',4'-tri-O-methyl-(+)-catechin | 29127-26-2

• 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: 5,3',4'-tri-O-methyl-(+)-catechin
• 英文别名: 3',4',5-tri-O-methyl-catechin；5,3',4'-trimethylcatechin；(2R,3S)-2-(3,4-dimethoxyphenyl)-5-methoxy-3,4-dihydro-2H-chromene-3,7-diol
• CAS: 29127-26-2
• 化学式: C₁₈H₂₀O₆
• 分子量: 332.353
• InChiKey: PNTYVQXZIQNKPC-SCLBCKFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.46
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  77.38
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5,3',4'-tri-O-methyl-(+)-catechin 、 3,4,5-三甲氧基苯甲酰氯 在 sodium hydroxide 作用下， 生成 hexa-O-methyl-(+)-catechin-7-gallate
  参考文献：
  名称：

  7-O-Galloyl-(+)-catechin and 3-O-galloylprocyanidin B-3 from Sanguisorba officinalis

  摘要：

  DOI：

  10.1016/0031-9422(83)80168-x
• 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 5,3',4'-tri-O-methyl-(+)-catechin
  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

• Saponin and sapogenol. XXXI. Chemical constituents of the seeds of Vigna angularis (Willd.) Ohwi et Ohashi. (1). Triterpenoidal sapogenols and 3-furanmethanol .BETA.-D-glucopyranoside.
  作者：ISAO KITAGAWA、HUIKANG WANG、MASAYUKI SAITO、MASAYUKI YOSHIKAWA

  DOI：10.1248/cpb.31.664

  日期：——

  3-Furanmethanol β-D-glucopyranoside (1) and (+)-catechin 7-O-β-D-glucopyranoside (3) were isolated from azuki beans, the seeds of Vigna angularis (WILLD.) OHWI et OHASHI (Leguminosae) and their structures were substantiated. The saponin mixture designated as total azukisaponin was also isolated from azuki beans. By means of enzymatic hydrolysis, acidic hydrolysis, and photochemical degradation, four genuine sapogenols, which included three known sapogenols, sophoradiol (7), soyasapogenol B (8), gypsogenic acid (9), and a new sapogenol named azukisapogenol (10), were isolated from total azukisaponin and the structure of 10 was elucidated. As one of the artifact sapogenols which were liberated by acidic hydrolysis of total azukisaponin, a new sapogenol named anhydrosophoradiol (5) was isolated and its structure was elucidated.

  从赤豆（Vigna angularis (Willd.) Ohwi et Ohashi 豆科）种子中分离得到3-呋喃甲醇β-D-吡喃葡糖苷（1）和（+）-儿茶素7-O-β-D-吡喃葡糖苷（3），并确定了它们的结构。从赤豆中还分离得到了总赤豆皂苷混合物。通过酶解、酸解和光化学降解，从总赤豆皂苷中分离出了4种真正的皂苷元，其中包括3种已知的皂苷元：染料木苷元（7）、大豆苷元B（8）、皂土酸（9）和一个新的皂苷元，命名为赤豆皂苷元（10），并阐明了其结构。作为总赤豆皂苷酸解释放的假皂苷元之一，分离得到了一个新的皂苷元，命名为无水染料木苷元（5），并阐明了其结构。
• LANGHAMMER, L.;LANGNER, C.;MAGNOLATO, D.;BOREL, CHR., SCI. PHARM., 57,(1989) N, C. 431-437
  作者：LANGHAMMER, L.、LANGNER, C.、MAGNOLATO, D.、BOREL, CHR.

  DOI：——

  日期：——