(+)-catechin 8-C-β-D-glucopyranoside | 103215-50-5

• 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: (+)-catechin 8-C-β-D-glucopyranoside
• 英文别名: (2S,3R,4R,5S,6R)-2-[(2R,3S)-2-(3,4-dimethoxyphenyl)-3-hydroxy-5,7-dimethoxy-3,4-dihydro-2H-chromen-8-yl]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 103215-50-5；105371-23-1
• 化学式: C₂₅H₃₂O₁₁
• 分子量: 508.522
• InChiKey: IYOPFENGPZEMND-YGMZYAMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  157
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  儿茶提取物 在 potassium carbonate 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 、 丙酮 为溶剂， 反应 14.5h， 生成 (+)-catechin 8-C-β-D-glucopyranoside
  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. XLVI Isolation and structures of stenophynins A and B, novel tannins from Quercus stenophylla Makino.
  作者：HIROAKI NISHIMURA、GEN-ICHIRO NONAKA、ITSUO NISHIOKA

  DOI：10.1248/cpb.34.3223

  日期：——

  Two novel tannins, stenophynins A and B, isolated from the bark of Quercus stenophylla MAKINO (Fagaceae), have been characterized on the basis of chemical and spectroscopic evidence as (+)-catechin 8-C-β-D-[2", 3" : 4", 6"-bis(S)-hexahydroxydiphenoyl]-glucopyranoside (1) and (+)-catechin 8-C-β-D-[2", 3"-(S)-hexahydroxydiphenoyl-6"-galloyl]-glucopyranoside (2), respectively.

  根据化学和光谱证据，从栎树树皮（椑科）中分离出两种新型单宁--儿茶素 A 和 B，它们分别是(+)-儿茶素 8-C-β-D-[2",3"：4"，6"-双(S)-六羟基二苯甲酰基]-吡喃葡萄糖苷(1)和(+)-儿茶素 8-C-β-D-[2"，3"-(S)-六羟基二苯甲酰基-6"-galloyl]-吡喃葡萄糖苷(2)。
• 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)。