2-(4-羟基-3-甲氧基苯基)乙基β-D-吡喃葡萄糖苷 | 120464-30-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-(4-羟基-3-甲氧基苯基)乙基β-D-吡喃葡萄糖苷
• 英文名称: 2-(4-hydroxy-3-methoxyphenyl)ethyl β-D-glucopyranoside
• 英文别名: 2-(3-hydroxy-4-methoxyphenyl)-ethyl-O-β-D-glucopyranoside；2-(4-Hydroxy-3-methoxyphenyl)ethyl I(2)-D-glucopyranoside；(2R,3R,4S,5S,6R)-2-[2-(4-hydroxy-3-methoxyphenyl)ethoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 120464-30-4
• 化学式: C₁₅H₂₂O₈
• 分子量: 330.335
• InChiKey: CGDVBCBYNROVPI-UXXRCYHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  129
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  对羟基苯乙醇 在 甲醇 、 oxone||potassium monopersulfate triple salt 、 sodium methylate 、 sodium bromide 、 copper(I) bromide 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 21.5h， 生成 2-(4-羟基-3-甲氧基苯基)乙基β-D-吡喃葡萄糖苷
  参考文献：
  名称：

  三种天然苯乙基糖苷的全合成

  摘要：

  摘要 在苯环上具有酚或甲氧基官能团的苯乙基糖苷是自然界中广泛存在的物质。这类化合物已被证明具有抗氧化，抗炎和抗癌活性。然而，它们中的一些不是天然丰富的，因此期望合成此类分子。在本文中，首先从易于获得的材料中完全合成了天然苯乙基糖苷3和4，总收率分别为50.5％和40.1％。并描述了一种新的合成途径，以46.2％的收率获得天然的苯乙基糖苷2。

  DOI：

  10.1080/10286020.2020.1724970

文献信息

• 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.
• Total synthesis of three natural phenethyl glycosides
  作者：Hong-Bo Dong、Jian Meng、Zhong-Quan Yao、Hong-Bing Luo、Jing-Xia Zhang、Wei-Hong Du、Ke-Hui Tang、Sheng-Hua Cao

  DOI：10.1080/10286020.2020.1724970

  日期：2021.3.4

  Abstract Phenethyl glycosides having phenolic or methoxy functions at benzene rings are substances widely occurring in nature. This kind of compounds has been shown to have anti-oxidant, anti-inflammatory, and anticancer activities. However, some of them are not naturally abundant, thus the synthesis of such molecules is desirable. In this paper, natural phenethyl glycosides 3 and 4 were first totally

  摘要 在苯环上具有酚或甲氧基官能团的苯乙基糖苷是自然界中广泛存在的物质。这类化合物已被证明具有抗氧化，抗炎和抗癌活性。然而，它们中的一些不是天然丰富的，因此期望合成此类分子。在本文中，首先从易于获得的材料中完全合成了天然苯乙基糖苷3和4，总收率分别为50.5％和40.1％。并描述了一种新的合成途径，以46.2％的收率获得天然的苯乙基糖苷2。