procyanidin B-3 7-O-β-D-glucopyranoside | 105330-57-2

• 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: procyanidin B-3 7-O-β-D-glucopyranoside
• 英文别名: Procyanidin B3 7-glucoside；(2R,3S)-2-(3,4-dihydroxyphenyl)-8-[(2R,3S,4S)-2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol
• CAS: 105330-57-2
• 化学式: C₃₆H₃₆O₁₇
• 分子量: 740.672
• InChiKey: JQKHCULJNVYRGT-XOLODHEFSA-N

物化性质

• 沸点：
  1059.7±65.0 °C(Predicted)
• 密度：
  1.731±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  53
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  300
• 氢给体数：
  13
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  procyanidin B-3 7-O-β-D-glucopyranoside 在 sodium hydroxide 、 sodium metaborate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 4.75h， 生成 (2R,3S)-4-(3-hydroxy-5,7-dimethoxychroman-2-yl)benzene-1,2-diol
  参考文献：
  名称：

  Tannins and related compounds. XLV Rhubarb. 5 Isolation and characterization of flavan-3-ol and procyanidin glucosides.

  摘要：

  通过对优质商品大黄（Choukichio：？(+)-catechin 5-O-β-D-glucopyranoside (1)、(+)-catechin 7-O-β-D-glucopyranoside (2)、procyanidin B-2 8-C-β-D-glucopyranoside (3) 和 procyanidin B-2 6-C-β-D-glucopyranoside (4)。根据化学和光谱证据，前两种化合物被定性为(+)-儿茶素 3'-O-β-D-Glucopyranoside (5)、(+)-catechin 4'-O-β-D-glucopyranoside (6)、(+)-catechin 7, 3'-di-O-β-D-glucopyranoside (7)、(+)-catechin 5, 3'-di-O-β-D-glucopyranoside (8)、(+)-catechin 3'、4'-二-O-β-D-吡喃葡萄糖苷 (9)，(+)-儿茶素 5，4'-二-O-β-D-吡喃葡萄糖苷 (10)，(+)-儿茶素 8-C-β-D-吡喃葡萄糖苷 (11)，(+)-儿茶素 6-C-β-D-吡喃葡萄糖苷 (12)、原花青素 B-3 7-O-β-D-Glucopyranoside (13)、原花青素 B-1 8-C-β-D-Glucopyranoside (14) 和原花青素 B-1 6-C-β-D-Glucopyranoside (15)。

  DOI：

  10.1248/cpb.34.3208

文献信息

• Tannins and related compounds. XLV Rhubarb. 5 Isolation and characterization of flavan-3-ol and procyanidin glucosides.
  作者：YOSHIKI KASHIWADA、GEN-ICHIRO NONAKA、ITSUO NISHIOKA

  DOI：10.1248/cpb.34.3208

  日期：——

  A chemical examination of high-quality commercial rhubarb (Choukichio : ?? ?? ?? ) has led to the isolation and characterization of eight flavan-3-ol glucosides and three proanthocyanidin glucosides, together with several known compounds, i.e., (+)-catechin 5-O-β-D-glucopyranoside (1), (+)-catechin 7-O-β-D-glucopyranoside (2), procyanidin B-2 8-C-β-D-glucopyranoside (3) and procyanidin B-2 6-C-β-D-glucopyranoside (4). On the basis of chemical and spectroscopic evidence, the former compounds were characterized as (+)-catechin 3'-O-β-D-glucopyranoside (5), (+)-catechin 4'-O-β-D-glucopyranoside (6), (+)-catechin 7, 3'-di-O-β-D-glucopyranoside (7), (+)-catechin 5, 3'-di-O-β-D-glucopyranoside (8), (+)-catechin 3', 4'-di-O-β-D-glucopyranoside (9), (+)-catechin 5, 4'-di-O-β-D-glucopyranoside (10), (+)-catechin 8-C-β-D-glucopyranoside (11), (+)-catechin 6-C-β-D-glucopyranoside (12), procyanidin B-3 7-O-β-D-glucopyranoside (13), procyanidin B-1 8-C-β-D-glucopyranoside (14) and procyanidin B-1 6-C-β-D-glucopyranoside (15).

  通过对优质商品大黄（Choukichio：？(+)-catechin 5-O-β-D-glucopyranoside (1)、(+)-catechin 7-O-β-D-glucopyranoside (2)、procyanidin B-2 8-C-β-D-glucopyranoside (3) 和 procyanidin B-2 6-C-β-D-glucopyranoside (4)。根据化学和光谱证据，前两种化合物被定性为(+)-儿茶素 3'-O-β-D-Glucopyranoside (5)、(+)-catechin 4'-O-β-D-glucopyranoside (6)、(+)-catechin 7, 3'-di-O-β-D-glucopyranoside (7)、(+)-catechin 5, 3'-di-O-β-D-glucopyranoside (8)、(+)-catechin 3'、4'-二-O-β-D-吡喃葡萄糖苷 (9)，(+)-儿茶素 5，4'-二-O-β-D-吡喃葡萄糖苷 (10)，(+)-儿茶素 8-C-β-D-吡喃葡萄糖苷 (11)，(+)-儿茶素 6-C-β-D-吡喃葡萄糖苷 (12)、原花青素 B-3 7-O-β-D-Glucopyranoside (13)、原花青素 B-1 8-C-β-D-Glucopyranoside (14) 和原花青素 B-1 6-C-β-D-Glucopyranoside (15)。