(-)-epicatechin 6-C-β-D-glucopyranoside | 103215-49-2

• 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: (-)-epicatechin 6-C-β-D-glucopyranoside
• 英文别名: (-)-epicatechin-6-C-β-D-glucopyranoside；6-C-glucopyranosylepicatechin；(2R,3R)-2-(3,4-dihydroxyphenyl)-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,4-dihydro-2H-chromene-3,5,7-triol
• CAS: 103215-49-2
• 化学式: C₂₁H₂₄O₁₁
• 分子量: 452.415
• InChiKey: PWMSPKVTJLJDDS-OFMZUWIHSA-N

物化性质

• 沸点：
  867.5±65.0 °C(Predicted)
• 密度：
  1.713±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  201
• 氢给体数：
  9
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (-)-epicatechin 6-C-β-D-glucopyranoside 、 硫酸二甲酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 3.0h， 生成 (2S,3R,4R,5S,6R)-2-[(2R,3R)-2-(3,4-Dimethoxy-phenyl)-3-hydroxy-5,7-dimethoxy-chroman-6-yl]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol
  参考文献：
  名称：

  Tannins and related compounds. XXXVIII. Isolation and characterization of flavan-3-ol glucosides and procyanidin oligomers from cassia bark (Cinnamomum cassia Blume).

  摘要：

  通过对肉桂树皮进行化学研究，分离出三种黄烷-3-醇葡糖苷（1-3）和三种低聚原花青素（4-6），分别命名为肉桂单宁 A2-A4，以及(-)-表儿茶素(7)、原花青素 B-2 (8)、B-5 (9)和 C-1 (11)和一种双链原花青素(10)。根据化学和光谱证据，化合物 1-3 的特征分别是(-)-表儿茶素 3-O-、8-C-和 6-C-β-D 吡喃葡萄糖苷，而化合物 4-6 则分别是四聚、五聚和六聚原花青素，完全由通过 C(4β)-C(8) 键线性连接的(-)-表儿茶素单元组成。

  DOI：

  10.1248/cpb.34.633
• 作为产物：
  描述：

  6-C-β-D-glucopyranosyl(-)-epicatechin 4-β-benzylthioether 在 Raney nickel (W-4) 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 0.5h， 生成 (-)-epicatechin 6-C-β-D-glucopyranoside
  参考文献：
  名称：

  Tannins and related compounds. XXXIX. Procyanidin C-glucosides and an acylated flavan-3-ol glucoside from the barks of Cinnamomum cassia Blume and C. obtusifolium Nees.

  摘要：

  除了原花青素 B-1 (4)、B-2 (5)、B-5 (6)和 B-7 (7)以及双链原花青素 A-2 (8)之外，还从肉桂 Cinnamomumum cassia BLUME( ?? ?? ?? ?? )( 月桂科)树皮中分离出两种新的原花青素葡萄糖苷，并根据核碳-13 磁性原花青素 B-2 8-C- 和 6-C-β-D-Glucopyranosides (1 和 2)的特征，将其分别命名为原花青素 B-2 8-C- 和 6-C-β-D-Glucopyranosides (1和2)。) (Lauraceae) 树皮中分离出了两种新的原花青素苷，并根据质子和碳 13 核磁共振检测以及硫代降解的结果，将其分别定性为原花青素 B-2 8-C- 和 6-C-β-D-Glucopyranosides (1 和 2)。此外，还从肉桂（Cinnamomum obtusifolium NEES）树皮中分离出一种酰化黄烷-3-醇葡萄糖苷（3），以及已知的原花青素 B-1（4）、B-2（5）、B-5（6）和 A-2（8）。根据化学和光谱证据，3 的结构被确定为 (+)-catechin 5-O-β-D-(2"-O-feruloyl-6"-O-p-coumaroyl)-glucopyranoside 。

  DOI：

  10.1248/cpb.34.643

文献信息

• Application of a Molecular Sensory Science Approach to Alkalized Cocoa (<i>Theobroma cacao</i>):  Structure Determination and Sensory Activity of Nonenzymatically C-Glycosylated Flavan-3-ols
  作者：Timo Stark、Thomas Hofmann

  DOI：10.1021/jf062403+

  日期：2006.12.1

  Application of comparative taste dilution analyses on nonalkalized and alkalized cocoa powder revealed the detection of a velvety, smoothly astringent tasting fraction, which was predominantly present in the alkalized sample. LC-MS/MS analysis, 1D- and 2D-NMR, and CD spectroscopy as well as model alkalization reactions led to the unequivocal identification of the velvety, smoothly astringent molecules as a series of catechin- and epicatechin-C-glycopyranosides. Besides the previously reported (-)-epicatechin-8-C-beta-D-galactopyranoside, additional flavan-3-ol-C-glycosides, namely, (-)-epicatechin-8- C-beta-D-glucopyranoside, (-)-catechin-8-C-beta-D-glucopyranoside, (-)-catechin-6-C-beta-D-glucopyranoside, (-)-epicatechin-6-C-beta-D-glucopyranoside, (-)-catechin-8-C-beta-D-galactopyranoside, (-)-catechin-6- C-beta-D-galactopyranoside, (-)-catechin-6-C, 8-C-beta-D-diglucopyranoside, (-)-epicatechin-6-C, 8-C-beta-D- digalactopyranoside, (-)-catechin-6-beta-C-D-digalactopyranoside, and epicatechin-6-C, 8-C-beta-Ddiglucopyranoside, were identified for the first time in cocoa. Most surprisingly, these phenol glycoconjugates were demonstrated by model experiments to be formed via a novel nonenzymatic C-glycosylation of flavan-3-ols. Using the recently developed half-tongue test, human recognition thresholds for the astringent and mouth-drying oral sensation were determined to be between 1.1 and 99.5 mu mol/L (water) depending on the sugar and the intramolecular binding position as well as the aglycone.
• Tannins and related compounds. XXXVIII. Isolation and characterization of flavan-3-ol glucosides and procyanidin oligomers from cassia bark (Cinnamomum cassia Blume).
  作者：SATOSHI MORIMOTO、GEN-ICHIRO NONAKA、ITSUO NISHIOKA

  DOI：10.1248/cpb.34.633

  日期：——

  A chemical examination of the bark of Cinnamomum cassia( ?? ?? ?? ?? : Lauraceae) has led to the isolation of three flavan-3-ol glucosides (1-3) and three oligomeric procyanidins (4-6) named cinnamtannins A2-A4, together with (-)-epicatechin(7), procyanidins B-2 (8), B-5 (9) and C-1 (11), and a doubly-linked proanthocyanidin (10). On the basis of chemical and spectroscopic evidence, compounds 1-3 were characterized as (-)-epicatechin 3-O-, 8-C- and 6-C-β-D-glucopyranosides, respectively, while compounds 4-6 were shown to be tetrameric, pentameric and hexameric procyanidins, respectively, consisting exclusively of (-)-epicatechin units linked linearly through C(4β)-C(8) bonds.

  通过对肉桂树皮进行化学研究，分离出三种黄烷-3-醇葡糖苷（1-3）和三种低聚原花青素（4-6），分别命名为肉桂单宁 A2-A4，以及(-)-表儿茶素(7)、原花青素 B-2 (8)、B-5 (9)和 C-1 (11)和一种双链原花青素(10)。根据化学和光谱证据，化合物 1-3 的特征分别是(-)-表儿茶素 3-O-、8-C-和 6-C-β-D 吡喃葡萄糖苷，而化合物 4-6 则分别是四聚、五聚和六聚原花青素，完全由通过 C(4β)-C(8) 键线性连接的(-)-表儿茶素单元组成。
• Tannins and related compounds. XXXIX. Procyanidin C-glucosides and an acylated flavan-3-ol glucoside from the barks of Cinnamomum cassia Blume and C. obtusifolium Nees.
  作者：SATOSHI MORIMOTO、GEN-ICHIRO NONAKA、ITSUO NISHIOKA

  DOI：10.1248/cpb.34.643

  日期：——

  Along with procyanidins B-1 (4), B-2 (5), B-5 (6) and B-7 (7), and the doubly linked proanthocyanidin, A-2 (8), two new procyanidin glucosides have been isolated from the bark of Cinnamomum cassia BLUME( ?? ?? ?? ?? )(Lauraceae), and characterized as procyanidin B-2 8-C- and 6-C-β-D-glucopyranosides (1 and 2, respectively) on the basis of proton and carbon-13 nuclear magnetic resonance examinations and the results of thiolytic degradation. In addition, from the bark of Cinnamomum obtusifolium NEES( ?? ?? ?? ?? ?? ?? ), an acylated flavan-3-ol glucoside (3) has been isolated, together with the known proanthocyanidins B-1 (4), B-2 (5), B-5 (6) and A-2 (8). The structure of 3 has been established to be (+)-catechin 5-O-β-D-(2"-O-feruloyl-6"-O-p-coumaroyl)-glucopyranoside on the basis of chemical and spectral evidence.

  除了原花青素 B-1 (4)、B-2 (5)、B-5 (6)和 B-7 (7)以及双链原花青素 A-2 (8)之外，还从肉桂 Cinnamomumum cassia BLUME( ?? ?? ?? ?? )( 月桂科)树皮中分离出两种新的原花青素葡萄糖苷，并根据核碳-13 磁性原花青素 B-2 8-C- 和 6-C-β-D-Glucopyranosides (1 和 2)的特征，将其分别命名为原花青素 B-2 8-C- 和 6-C-β-D-Glucopyranosides (1和2)。) (Lauraceae) 树皮中分离出了两种新的原花青素苷，并根据质子和碳 13 核磁共振检测以及硫代降解的结果，将其分别定性为原花青素 B-2 8-C- 和 6-C-β-D-Glucopyranosides (1 和 2)。此外，还从肉桂（Cinnamomum obtusifolium NEES）树皮中分离出一种酰化黄烷-3-醇葡萄糖苷（3），以及已知的原花青素 B-1（4）、B-2（5）、B-5（6）和 A-2（8）。根据化学和光谱证据，3 的结构被确定为 (+)-catechin 5-O-β-D-(2"-O-feruloyl-6"-O-p-coumaroyl)-glucopyranoside 。