2-(4-hydroxyphenyl)ethyl β-D-galactopyranoside | 850232-16-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(4-hydroxyphenyl)ethyl β-D-galactopyranoside
• 英文别名: 4-hydroxyphenylethyl-β-D-galactopyranoside；p-hydroxyphenylethyl-O-β-galactoside；tyrosol galactoside；p-Hydroxyphenethyl beta-d-galactopyranoside；(2R,3R,4S,5R,6R)-2-(hydroxymethyl)-6-[2-(4-hydroxyphenyl)ethoxy]oxane-3,4,5-triol
• CAS: 850232-16-5
• 化学式: C₁₄H₂₀O₇
• 分子量: 300.309
• InChiKey: ILRCGYURZSFMEG-MBJXGIAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  21
• 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：
  120
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-(4-甲基羰基氧基苯基)-1-乙醇 在 甲醇 、 sodium methylate 、 silver carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 40.67h， 生成 2-(4-hydroxyphenyl)ethyl β-D-galactopyranoside
  参考文献：
  名称：

  Development of a Kilogram-Scale Synthesis of Salidroside and Its Analogs

  摘要：

  An efficient, safe, and viable process has been developed for large-scale preparation of salidroside, a natural product. The process consists of two chemical steps, which produce the salidroside on a multikilogram scale with 72% overall yield and >98% purity. A series of novel salidroside analogs were prepared according to the same method.

  DOI：

  10.1080/00397911.2010.515332

文献信息

• Synthesis, Biological Activity of Salidroside and Its Analogues
  作者：Yibing Guo、Yahong Zhao、Cheng Zheng、Ying Meng、Yumin Yang

  DOI：10.1248/cpb.58.1627

  日期：——

  Salidroside is a phenylpropanoid glycoside isolated from Rhodiola rosea L., a traditional Chinese medicinal plant, and has displayed a broad spectrum of pharmacological properties. In this paper, about 18 novel salidroside analogues were prepared through Koenigs–Knorr method, the effects of these compounds over PC12 was assessed with the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) method. The novel compounds differ in the substituents attached to the benzene ring or in the glycosyl donor. According to the data, compounds (3,5-dimethoxyphenyl)methyl β-D-glucopyranoside and (3,5-dimethoxyphenyl)methyl β-D-galactopyranoside with methoxy group at 3 and 5-positions of the benzene ring were the most viability at concentration of 300 μmol/l and 60 μmol/l, respectively.

  红景天苷是从传统中草药红景天中分离得到的一种苯丙素苷类化合物，具有广泛的药理活性。本文通过Koenigs-Knorr方法合成了约18种新颖的红景天苷类似物，并利用3-(4,5-二甲基噻唑-2-基)-2,5-二苯基四唑溴盐（MTT）法评估了这些化合物对PC12细胞的影响。这些新颖化合物在苯环上的取代基或糖基供体方面有所不同。根据数据，苯环3和5位带有甲氧基的(3,5-二甲氧基苯基)甲基β-D-葡萄吡喃糖苷和(3,5-二甲氧基苯基)甲基β-D-半乳吡喃糖苷在浓度分别为300 μmol/L和60 μmol/L时显示出最高的细胞生存力。
• 半乳糖型红景天苷及其衍生物的制备方法
  申请人：山东大学

  公开号：CN106543244B

  公开（公告）日：2019-07-26

  本发明涉及半乳糖型红景天苷及其衍生物的制备方法，包括如下步骤：(1)采用磷酸缓冲液配制乳糖浓度为0.1M～1M、对羟基苯乙醇浓度为0.05M～0.5M、β‑半乳糖苷酶浓度为0.004mg～4mg/mL的反应体系；(2)将反应体系于30～50℃条件下反应5～30分钟，终止反应，固液分离，取上清液；(3)将上清液，经分离、干燥后，制得半乳糖型红景天苷及其衍生物。该方法底物便宜，反应快速，操作简便，省时省力，生产成本低，应用前景广阔。
• Comparative study of relationship between structure of phenylethanoid glycopyranosides and their activities using cell-free assays and human cells cultured in vitro
  作者：Eva Horvathova、Maria Mastihubova、Elena Karnisova Potocka、Peter Kis、Eliska Galova、Andrea Sevcovicova、Martina Klapakova、Luba Hunakova、Vladimir Mastihuba

  DOI：10.1016/j.tiv.2019.104646

  日期：2019.12

  The study focused on protective potential of phytochemicals applicable in prevention and health protection is of great importance. Various structures of these compounds and a wide range of their biological activities have inspired organic chemists to sythesize their effective analogues in order to further increase their efficacy.The aims of our study were (i) to synthesize phenylethanoid glycopyranosides: salidroside (SALI - tyrosol beta-Dglucopyranoside), tyrosol beta-D-galactopyranoside (TYBGAL), tyrosol alpha-D-galactopyranoside (TYAGAL), tyrosol alpha-D-mannopyranoside (TYAMAN), hydroxytyrosol alpha-D-mannopyranoside (HOTAMA), homosyringyl beta-D-glucopyranoside (HSYGLU), hydroxytyrosol beta-D-xylopyranoside (HOTXYL) and hydroxysalidroside (HOSALI); (ii) to determine their antioxidant capacities (cell-free approaches); (iii) to evaluate their cytotoxicity (MTT test), protectivity against hydrogen peroxide (H2O2; comet assay) and effect on the intracellular glutathione level (iGSH; flow cytometry) in experimental system utilizing human hepatoma HepG2 cells.HOSALI, HOTAMA, HOTXYL and HSYGLU manifested the highest antioxidant capacity in cell-free assays and they were most active in protection of HepG2 cells against H2O2. On the other hand, pre-treatment of HepG2 cells with SALI had protective effects even though SALT displayed almost no activity in cell-free assays.Differences in the efficacy of the analogues revealed that structures of their molecules in terms of aglycone combined with sugar moiety affect their activities.
• Enzymatic synthesis of tyrosol glycosides
  作者：Elena Potocká、Mária Mastihubová、Vladimír Mastihuba

  DOI：10.1016/j.molcatb.2014.12.017

  日期：2015.3

  For the purpose of synthesis of tyrosol beta-D-glucopyranoside (salidroside) and its beta-D- and alpha-D-galactopyranoside analogues, transglycosylation of tyrosol with fungal glycosidases (from Aspergillus niger and Aspergillus oryzae) was executed. Cellobiose, lactose and melibiose served as glycosyl donor giving 6.7% yield of salidroside, 10.9% of tyrosol beta-D-galactopyranoside, and 32.2% of alpha-D-galactopyranoside. The glycosylations proceeded on the primary hydroxyl of the tyrosol. (C) 2015 Elsevier B.V. All rights reserved.
• Development of a Kilogram-Scale Synthesis of Salidroside and Its Analogs
  作者：Tianyao Shi、Hui Chen、Linlin Jing、Xueying Liu、Xiaoli Sun、Ru Jiang

  DOI：10.1080/00397911.2010.515332

  日期：2011.9.1

  An efficient, safe, and viable process has been developed for large-scale preparation of salidroside, a natural product. The process consists of two chemical steps, which produce the salidroside on a multikilogram scale with 72% overall yield and >98% purity. A series of novel salidroside analogs were prepared according to the same method.