Proanthocyanidin A-2-heptamethylether | 55626-24-9

• 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: Proanthocyanidin A-2-heptamethylether
• 英文别名: Proanthocyanidin A-2-heptamethylaether；(1R,5R,6R,13S,21R)-5,13-bis(3,4-dimethoxyphenyl)-9,17,19-trimethoxy-4,12,14-trioxapentacyclo[11.7.1.02,11.03,8.015,20]henicosa-2,8,10,15(20),16,18-hexaene-6,21-diol
• CAS: 55626-24-9
• 化学式: C₃₇H₃₈O₁₂
• 分子量: 674.702
• InChiKey: LLMOYBYCVKZDGW-COFBMEKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  49
• 可旋转键数：
  9
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  133
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  Proanthocyanidin A-2-heptamethylether 在 sodium tetrahydroborate 、 9-芴酮 、 potassium tert-butylate 作用下， 以 甲醇 、 苯 为溶剂， 反应 9.08h， 生成 (1R,5R,6S,13S,21R)-5,13-bis(3,4-dimethoxyphenyl)-9,17,19-trimethoxy-4,12,14-trioxapentacyclo[11.7.1.02,11.03,8.015,20]henicosa-2,8,10,15(20),16,18-hexaene-6,21-diol
  参考文献：
  名称：

  Nonaka, Gen-Ichiro; Morimoto, Satoshi; Kinjo, Jun-Ei, Chemical and pharmaceutical bulletin, 1987, vol. 35, # 1, p. 149 - 155

  摘要：

  DOI：
• 作为产物：
  描述：

  重氮甲烷 、 procyanidin A2 以 甲醇 、 乙醚 为溶剂， 反应 72.0h， 以8 mg的产率得到Proanthocyanidin A-2-heptamethylether
  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

• Oligomeric flavanoids. Part 25. Cleavage of the acetal functionality in A-type proanthocyanidins
  作者：Petrus J. Steynberg、Annemarie Cronjé、Jan P. Steynberg、Barend C.B. Bezuidenhoudt、E.Vincent Brandt、Daneel Ferreira

  DOI：10.1016/s0040-4020(96)01149-0

  日期：1997.2

  and A-2 2 are subject to facile cleavage of the acetal functionality with sodium cyanoboranuide in trifluoroacetic acid at 0°C. This straight forward chemical method permits the unambiguous establishment of the absolute configuration of the DEF-flavanyl unit and the D-ring carbon and oxygen atoms that are involved in the double linkage of the A-class proanthocyanidins.

  原花青素A-1 1和A-2 2的七-O-甲基醚3和4在三氟乙酸中于0℃下容易裂解缩醛官能团。这种简单的化学方法可以明确建立涉及A级原花青素双键的DEF-黄烷酰基单元和D环碳原子和氧原子的绝对构型。
• Nonaka, Gen-Ichiro; Morimoto, Satoshi; Kinjo, Jun-Ei, Chemical and pharmaceutical bulletin, 1987, vol. 35, # 1, p. 149 - 155
  作者：Nonaka, Gen-Ichiro、Morimoto, Satoshi、Kinjo, Jun-Ei、Nohara, Toshihiro、Nishioka, Itsuo

  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.