2-(3,4,5-trihydroxyphenyl)ethyl β-D-glucopyranoside | 1350703-18-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(3,4,5-trihydroxyphenyl)ethyl β-D-glucopyranoside
• 英文别名: 2-(3,4,5-Trihydroxyphenyl)ethyl beta-d-glucopyranoside；(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[2-(3,4,5-trihydroxyphenyl)ethoxy]oxane-3,4,5-triol
• CAS: 1350703-18-2
• 化学式: C₁₄H₂₀O₉
• 分子量: 332.307
• InChiKey: DFYCVRNHYXPTFD-RGCYKPLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  160
• 氢给体数：
  7
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  3,4,5-三(苄氧基)苯甲醇 在 lithium aluminium tetrahydride 、 氯化亚砜 、 18-冠醚-6 、 palladium 10% on activated carbon 、 氢气 、 sodium methylate 、 N,N-二甲基甲酰胺 、 silver carbonate 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 反应 72.5h， 生成 2-(3,4,5-trihydroxyphenyl)ethyl β-D-glucopyranoside
  参考文献：
  名称：

  β-葡糖胆素的酰胺 N-糖苷衍生物的设计：一种稳定、有效且特异性的醛糖还原酶抑制剂

  摘要：

  β-Glucogallin（BGG），所述的主要成分余甘厚朴药用植物，是醛糖还原酶（AKR1B1）的强效的和选择性的抑制剂。通过高产、高效的合成引入了新的键（醚/三唑/酰胺）以替代不稳定的酯，并开发了 BGG 的原始两步 (90%) 制备。在体外和使用转基因晶状体器官培养物评估了对 AKR1B1 的抑制作用，发现酰胺连接的葡萄糖苷 (BGA) 是一种稳定、有效和选择性的治疗糖尿病眼病的先导药物。

  DOI：

  10.1021/jm401311d

文献信息

• [EN] APPLICATION OF SALIDROSIDE DERIVATIVE IN SKIN-WHITENING AGENT FOR EXTERNAL USE<br/>[FR] APPLICATION D'UN DÉRIVÉ DE SALIDROSIDE DANS UN AGENT DE BLANCHIMENT DE LA PEAU À USAGE EXTERNE<br/>[ZH] 红景天苷衍生物在皮肤美白外用剂中的应用
  申请人：SHANGHAI CHENGMU BIOLOGICAL TECH CO LTD

  公开号：WO2021129241A1

  公开（公告）日：2021-07-01

  本发明提出了红景天苷衍生物在皮肤美白外用剂中的应用，属于护肤品技术领域。本发明可在增强红景天苷的美白活性同时充分利用红景天苷糖环的保护作用，通过改构红景天苷的酚残基得到红景天苷-plus(SP-037)，即1-(3,5-二羟基苯基)乙基-β-D-葡萄糖苷和/或其盐，并通过系列实验拟检测其美白效果。
• Zheng, Cheng; Guo, Yibing; Meng, Ying, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2013, vol. 52, # 5, p. 654 - 664
  作者：Zheng, Cheng、Guo, Yibing、Meng, Ying、Dou, Sufeng、Shao, Jian、Yang, Yumin

  DOI：——

  日期：——
• Free radical scavenging and hepatoprotective effects of salidroside analogs on CCl4-induced cytotoxicity in LO2 cells
  作者：Yibing Guo、Cheng Zheng、Wen Xu、Yongxing Si、Sufeng Dou、Yumin Yang

  DOI：10.1007/s00044-012-0247-z

  日期：2013.5

  Salidroside, a phenylpropanoid glycoside isolated from a traditional Chinese medicinal plant Rhodiola rosea L. displays a broad spectrum of pharmacological properties. It has been found to play a hepatoprotective role in liver diseases through inhibiting apoptosis of hepatocytes and proliferation of hepatic stellate cells, decreasing serum aminotransferase, reversing hepatic fibrosis, and improving liver function. In this study as an ongoing study on the discovery and development of new hepatoprotective agents, about 12 novel glycosides were synthesized, and 2,2-diphenyl-1-picrylhydrazyl radical scavenge activity of each glycoside was evaluated. 2-(3,4,5-trihydroxyphenyl)ethyl beta-d-glucopyranoside (4g) and 2-(3,4,5-trihydroxyphenyl)ethyl beta-d-galactopyranoside (4h) exhibited significant activity prior to salidroside with an IC50 value of 38.05 and 35.85 mu M, respectively. The hepatoprotective effect of compounds 4g and 4h on CCl4-induced cytotoxicity in LO2 cells was assessed for further research.2-(3,4,5-Trihydroxyphenyl)ethyl beta-d-glucopyranoside (4g) and 2-(3,4,5-trihydroxyphenyl)ethyl beta-d-galactopyranoside (4h) exhibited significant hepatoprotective activity prior to salidroside.
• USE OF SALIDROSIDE DERIVATIVE IN EXTERNAL PREPARATION FOR SKIN WHITENING
  申请人：SHANGHAI CHEERMORE BIOLOGICAL TECHNOLOGY CO., LTD

  公开号：US20220142895A1

  公开（公告）日：2022-05-12

  The use of the compound or a pharmaceutically acceptable salt thereof in the preparation of an external preparation for skin whitening is provided, and the compound is shown in formula (I-1): The present disclosure can enhance the whitening activity of salidroside while taking full advantage of the protective effect of salidroside sugar ring, where the phenol residues of salidroside are restructured to obtain salidroside-plus (SP-037), which is 1-(3,5-dihydroxyphenyl)ethyl-β-D-glucoside and/or a salt thereof. The whitening effect of the compound is tested through a series of experiments.
• Design of an Amide <i>N</i>-Glycoside Derivative of β-Glucogallin: A Stable, Potent, and Specific Inhibitor of Aldose Reductase
  作者：Linfeng Li、Kun-Che Chang、Yaming Zhou、Biehuoy Shieh、Jessica Ponder、Adedoyin D. Abraham、Hadi Ali、Anson Snow、J. Mark Petrash、Daniel V. LaBarbera

  DOI：10.1021/jm401311d

  日期：2014.1.9

  inhibitor of aldose reductase (AKR1B1). New linkages (ether/triazole/amide) were introduced via high yielding, efficient syntheses to replace the labile ester, and an original two-step (90%) preparation of BGG was developed. Inhibition of AKR1B1was assessed in vitro and using transgenic lens organ cultures, which identified the amide linked glucoside (BGA) as a stable, potent, and selective therapeutic

  β-Glucogallin（BGG），所述的主要成分余甘厚朴药用植物，是醛糖还原酶（AKR1B1）的强效的和选择性的抑制剂。通过高产、高效的合成引入了新的键（醚/三唑/酰胺）以替代不稳定的酯，并开发了 BGG 的原始两步 (90%) 制备。在体外和使用转基因晶状体器官培养物评估了对 AKR1B1 的抑制作用，发现酰胺连接的葡萄糖苷 (BGA) 是一种稳定、有效和选择性的治疗糖尿病眼病的先导药物。