phloroglucinol-C-β-D-glucoside | 88885-05-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phloroglucinol-C-β-D-glucoside
• 英文别名: (2R,3S,4R,5R,6S)-2-(hydroxymethyl)-6-(2,4,6-trihydroxyphenyl)oxane-3,4,5-triol
• CAS: 88885-05-6
• 化学式: C₁₂H₁₆O₈
• 分子量: 288.254
• InChiKey: WHDIYCULVGAWGN-URYVQPGZSA-N

物化性质

• 沸点：
  549.2±50.0 °C(Predicted)
• 密度：
  1.731±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  151
• 氢给体数：
  7
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 phloroglucinol-C-β-D-glucoside 在 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 反应 24.0h， 以260 mg的产率得到1,3,5-triacetoxy-2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)benzene
  参考文献：
  名称：

  Synthesis of 1-[3,5-bis-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl)-2,4,6-trihydroxyphenyl]ethanone: An intermediate of potential usefulness for synthesis of bis-C-glucosyl flavonoids

  摘要：

  Bis-glycosylation of 3,5-dibenzyloxyphenol with 2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranosyl fluoride in a two-step sequence produced the bis-glucosylated product, 3,5-dibenzyloxy-2,6-bis-(2,3,4,6-tetra-O-benzyl-beta-D-glucopyranosyl)phenol. Subsequent hydrogenolytic debenzylation and acetylation gave the undeca-O-acetyl derivative, which, when subjected to a Friedel-Crafts acylation with borontrifluoride-acetic acid, gave the 4-C-acetyl target compound, 1-[3,5-bis-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-2,4,6-trihydroxyphenyl]-ethanone. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)00280-7
• 作为产物：
  描述：

  在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 24.0h， 生成 phloroglucinol-C-β-D-glucoside
  参考文献：
  名称：

  Synthesis of 1-[3,5-bis-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl)-2,4,6-trihydroxyphenyl]ethanone: An intermediate of potential usefulness for synthesis of bis-C-glucosyl flavonoids

  摘要：

  Bis-glycosylation of 3,5-dibenzyloxyphenol with 2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranosyl fluoride in a two-step sequence produced the bis-glucosylated product, 3,5-dibenzyloxy-2,6-bis-(2,3,4,6-tetra-O-benzyl-beta-D-glucopyranosyl)phenol. Subsequent hydrogenolytic debenzylation and acetylation gave the undeca-O-acetyl derivative, which, when subjected to a Friedel-Crafts acylation with borontrifluoride-acetic acid, gave the 4-C-acetyl target compound, 1-[3,5-bis-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-2,4,6-trihydroxyphenyl]-ethanone. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)00280-7

文献信息

• DIRECT CONDENSATION OF POLYHYDRIC PHENOLS WITH GLUCOSE
  作者：Jun-ichi Onodera、Mltsuru Takano、Yuji Kishi、Noriko Yokoyama、Ryosuke Ishida

  DOI：10.1246/cl.1983.1487

  日期：1983.10.5

  Acid-catalyzed direct condensation reaction of polyhydric phenols with free glucose in DMSO gave O-α-D-glucopyranoside in preference to its β-anomer; however, phloroglucinol and phloroacetophenone gave C-β-D-glucopyranoside instead.

  多羟基酚与游离葡萄糖在 DMSO 中的酸催化直接缩合反应得到 O-α-D-吡喃葡萄糖苷优先于其 β-端基异构体；然而，间苯三酚和间苯二酚产生了 C-β-D-吡喃葡萄糖苷。
• Oligomerization mechanism of tea catechins during tea roasting
  作者：Hitomi Morikawa、Keita Okuda、Yuji Kunihira、Aoi Inada、Chika Miyagi、Yosuke Matsuo、Yoshinori Saito、Takashi Tanaka

  DOI：10.1016/j.foodchem.2019.01.163

  日期：2019.7

  causes oligomerization of tea catechins, which decreases the astringency. The aim of this study was to elucidate the oligomerization mechanism. The 13C NMR spectrum of the oligomer fraction showed signals arising from catechin and sugar residues. Heating of epigallocatechin-3-O-gallate with 13C-labeled glucose (150 °C for 2 h) suggested that condensation of sugars with catechin A-rings caused the oligomerization

  焙烧绿茶会导致茶儿茶素低聚，从而降低涩味。这项研究的目的是阐明低聚机理。低聚物级分的13 C NMR光谱显示信号由儿茶素和糖残基引起。用13加热表没食子儿茶素-3 - O-没食子酸酯C标记的葡萄糖（150°C持续2 h）表明糖与儿茶素A环的缩合引起寡聚。通过加热较短时间（30分钟）获得的二聚体产物表明在糖和儿茶素A环之间发生了交联。此外，邻苯二酚A环模拟物间苯三酚与葡萄糖，甲基乙二醛和二羟基丙酮一起加热，证实了基本机理包括儿茶素A环次甲基碳与葡萄糖的羰基碳及其热解产物的反应。