quercetin 5‐O‐β‐D‐glucopyranoside | 34199-21-8

• 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: quercetin 5‐O‐β‐D‐glucopyranoside
• 英文别名: quercetin 5-O-β-D-glucopyranoside；quercetin-5-O-β-D-glucopyranoside；quercetin 5-O-β-D-glucoside；quercetin 5-O-β-D-glc；quercetin-3-O-glucoside；Quercetin-5-O-β-D-glucopyranosid；Quercetin 5-O-|A-D-glucopyranoside；2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• CAS: 34199-21-8
• 化学式: C₂₁H₂₀O₁₂
• 分子量: 464.383
• InChiKey: QJTYCCFDQWFJHU-HMGRVEAOSA-N

物化性质

• 熔点：
  264 °C
• 沸点：
  885.3±65.0 °C(Predicted)
• 密度：
  1.809±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  207
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  槲皮素 在 20 % Pd(OH)2/C 、 氢气 、 sodium methylate 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.5h， 生成 quercetin 5‐O‐β‐D‐glucopyranoside
  参考文献：
  名称：

  Regiospecific synthesis of quercetin O-β-d-glucosylated and O-β-d-glucuronidated isomers

  摘要：

  Quercetin, the polyphenolic compound, which has the highest daily intake, is well known for its protective effects against aging diseases and has received a lot of attention for this reason. Both quercetin 3-O-beta-D-glucuronide and quercetin 3'-O-beta-D-glucuronide are human metabolites, which, together with their regioisomers, are required for biological as well as physical chemistry studies. We present here a novel synthetic route based on the sequential and selective protections of the hydroxyl functions of quercetin allowing selective glycosylation, followed by TEMPO-mediated oxidation to the glucuronide. This methodology enabled us to synthesize the five O-beta-D-glucosides and four O-beta-D-glucuronides of quercetin, including the major human metabolite, quercetin 3-O-beta-D-glucuronide. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2011.03.110

文献信息

• Therapeutic agent of osteoporosis comprising an active ingredient of quercetin derivatives
  申请人：——

  公开号：US20020165169A1

  公开（公告）日：2002-11-07

  The present invention relates to a therapeutic agent for osteoporosis which comprises an active ingredient of quercetin derivatives. The quercetin derivatives of the invention can be practically applied for the treatment and prevention of osteoporosis, since they effectively inhibit osteoclast proliferation and stimulate osteoblast proliferation more than conventional therapeutic agents for osteoporosis, and increase trabecular bone area highly without changing hormone level in body and untoward effects on hematopoietic function and immune system.

  本发明涉及一种骨质疏松症治疗剂，其有效成分为槲皮素衍生物。本发明的槲皮素衍生物比传统的骨质疏松症治疗剂更能有效地抑制破骨细胞增殖和刺激成骨细胞增殖，在不改变体内激素水平、不对造血功能和免疫系统产生不良影响的情况下，能显著增加骨小梁面积，因此可实际应用于骨质疏松症的治疗和预防。
• A THERAPEUTIC AGENT OF OSTEOPOROSIS COMPRISING AN ACTIVE INGREDIENT OF QUERCETIN DERIVATIVES
  申请人：Korea Institute of Oriental Medicine

  公开号：EP1309326A1

  公开（公告）日：2003-05-14
• Therapeutic agent or osteoporosis comprising an active ingredient of quercetin derivatives
  申请人：——

  公开号：US20040162247A1

  公开（公告）日：2004-08-19

  The present invention relates to a therapeutic agent for osteoporosis which comprises an active ingredient of quercetin derivatives. The quercetin derivatives of the invention can be practically applied for the treatment and prevention of osteoporosis, since they effectively inhibit osteoclast proliferation and stimulate osteoblast proliferation more than conventional therapeutic agents for osteoporosis, and increase trabecular bone area highly without changing hormone level in body and untoward effects on hematopoietic function and immune system.
• COMPOSITIONS AND METHODS FOR PREVENTING AND TREATING RADIATION-INDUCED BYSTANDER EFFECTS CAUSED BY RADIATION OR RADIOTHERAPY
  申请人：THE REGENTS OF THE UNIVERSITY OF COLORADO

  公开号：US20200155502A1

  公开（公告）日：2020-05-21

  The invention provides novel compositions and methods for the treatment of Radiation-Induced Bystander Effects (RIBE), resulting from radiation exposure. In one preferred embodiment the inventions includes novel therapeutic agents, including but not limited to quercetin and quercetin analogs, as well as E64, CA074, CA074Me, that interfere with the activity of Cathepsin B.
• [EN] A THERAPEUTIC AGENT OF OSTEOPOROSIS COMPRISING AN ACTIVE INGREDIENT OF QUERCETIN DERIVATIVES<br/>[FR] AGENT THERAPEUTIQUE CONTRE L'OSTEOPOROSE COMPRENANT COMME PRINCIPE ACTIF DES DERIVES DE QUERCETINE
  申请人：KOREA INST ORIENTAL MEDICINE

  公开号：WO2002017909A1

  公开（公告）日：2002-03-07

  The present invention relates to a therapeutic agent of osteoporosis which comprises an active ingredient of quercetin derivatives. The quercetin derivatives of the invention can be practically applied for the treatment and prevention of osteoporosis, since they effectively inhibit osteoclast proliferation and stimulate osteoblast proliferation more than prior art therapeutic agents of osteoporosis, and increase trabecular bone area highly without changing hormone level in body and untoward effects on hematopoietic function and immune system.