反式-白藜芦醇 3-O-beta-D-葡糖苷酸 | 387372-17-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 反式-白藜芦醇 3-O-beta-D-葡糖苷酸
• 中文别名: (3S,4S,5S,6S)-3,4,5-三羟基-6-[3-羟基-5-[(E)-2-(4-羟基苯基)乙烯基]苯氧基]四氢吡喃-2-羧酸；反式-白藜芦醇3-O-beta-D-葡糖苷酸
• 英文名称: Resveratrol-3-O-glucuronide
• 英文别名: (E)-1-(5-hydroxy-3-O-β-D-glucopyranosidophenyl)-2-(4'-hydroxyphenyl)ethene；trans-resveratrol 3-O-β-D-glucuronide；trans-resveratrol-3-O-β-D-glucuronide；trans-resveratrol-7-O-β-D-glucuronide；resveratrol 3-O-β-D-glucuronide；resveratrol-3′-O-glucuronide；trans-Resveratrol 3-O-glucuronide；(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[3-hydroxy-5-[(E)-2-(4-hydroxyphenyl)ethenyl]phenoxy]oxane-2-carboxylic acid
• CAS: 387372-17-0
• 化学式: C₂₀H₂₀O₉
• 分子量: 404.373
• InChiKey: QWSAYEBSTMCFKY-OTPOQTMVSA-N

物化性质

• 熔点：
  >150?C (dec.)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  157
• 氢给体数：
  6
• 氢受体数：
  9

ADMET

代谢

白藜芦醇-3-O-葡萄糖苷酸是白藜芦醇已知的人体代谢物。

Resveratrol 3-O-glucuronide is a known human metabolite of Resveratrol.

来源:NORMAN Suspect List Exchange

反应信息

• 作为产物：
  描述：

  白藜芦醇 在 三氟化硼乙醚 、 ammonium acetate 、 水 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 29.58h， 生成 反式-白藜芦醇 3-O-beta-D-葡糖苷酸
  参考文献：
  名称：

  Practical Preparation of Resveratrol 3-O-β-D-Glucuronide

  摘要：

  A practical synthesis of resveratrol 3-O-beta-D-glucuronide, suitable for preparation of large quantities, was developed using selective deacetylation of resveratrol triacetate with ammonium acetate. A simplified procedure for large-scale preparation of resveratrol is also reported.

  DOI：

  10.1080/00397911.2011.585733

文献信息

• A concise synthesis of glucuronide metabolites of urolithin-B, resveratrol, and hydroxytyrosol
  作者：Ricardo Lucas、David Alcantara、Juan Carlos Morales

  DOI：10.1016/j.carres.2009.05.016

  日期：2009.7

  A simple and direct strategy to chemically synthesize O-beta-D-glucuronides of urolithin-B 4, resveratrol 5, and the corresponding hydroxytyrosol derivatives 6, 7 (as a regioisomeric mixture), and 8 is described. The critical glycosylation step has been optimized using a structurally simple phenol, urolithin-B, by modification of several reaction parameters (solvent, promoter, and glucuronide donor). Very high yields have been obtained in the first synthesis of the O-beta-D-glucuronide of urolithin-B 4. Extension of these reaction conditions was used for the synthesis of resveratrol-3-O-glucuronide 5 where a higher yield than previously reported was obtained by using the much more common trichloroacetimidate glucuronide donor. Finally, three O-beta-D-glucuronides of hydroxytyrosol 6, 7, and 8 have been synthesized for the first time using chemical synthesis. (C) 2009 Elsevier Ltd. All rights reserved.
• STEVIOL GLYCOSIDE SOLUBILITY ENHANCERS
  申请人：CARGILL, INCORPORATED

  公开号：US20190223481A1

  公开（公告）日：2019-07-25

  A solubilized steviol glycoside composition including one or more steviol glycosides and one or more steviol glycoside solubility enhancers can be used as a sweetener composition to sweeten other compositions (sweetenable compositions) such as foods, beverages, medicines, oral hygiene compositions, pharmaceuticals, nutraceuticals, and the like.