10230-17-8, 3-O-Benzyl-D-glucopyranose,
CAS:10230-17-8
C13H18O6 / 270.28
MFCD00051212
3-O-苄基-D-葡萄糖,
3-O-Benzyl-D-glucopyranose is a molecule that has been optimized for its autodock score. It binds to the active site of peptidases, which are enzymes that break down proteins in the body. 3-O-Benzyl-D-glucopyranose is a nauclea that can be used as a pharmacokinetic (PK) or pharmacodynamic (PD) inhibitor. Nauclea have shown effectiveness against diabetes by preventing the breakdown of glucose, which is an important energy source for cells. 3-O-Benzyl-D-glucopyranose has also been found to be an effective inhibitor of DPPIV, which is an enzyme involved in breaking down insulin and other hormones in blood circulation. In vitro studies have shown that it may also have antiaging properties due to its ability to inhibit production of inflammatory cytokines such as IL1β, IL6, and TNFα.
3-O-Benzyl-beta-D-glucose is a chemical compound with various physical, chemical, and biological properties. It is a disaccharide derivative consisting of a glucose moiety attached to a benzyl group through an ether linkage. In this paper, we will discuss various aspects of 3-O-Benzyl-beta-D-glucose. We will examine its definition and background, physical and chemical properties, synthesis and characterization, analytical methods, biological properties, toxicity and safety in scientific experiments, applications in scientific experiments, current state of research, potential implications in various fields of research and industry, limitations, and future directions.
Definition and Background:
3-O-Benzyl-beta-D-glucose is a disaccharide derivative consisting of a glucose moiety attached to a benzyl group through an ether linkage. It has a molecular formula of C13H18O6 and a molecular weight of 270.28 g/mol. This chemical compound is commonly used in pharmaceutical research as a starting material to synthesize various bioactive molecules. It is also used as a ligand in metal catalysis and chiral organic synthesis.
Physical and Chemical Properties:
3-O-Benzyl-beta-D-glucose is a white solid that is soluble in water, methanol, and ethanol. It has a melting point of 110-112 °C and a boiling point of 521.2 °C at 760 mmHg. The compound has a refractive index of 1.551, and its density is 1.47 g/cm^3 at 25 °C. It is stable under normal conditions and does not decompose readily. The chemical structure of 3-O-Benzyl-beta-D-glucose is shown in Figure 1.
Synthesis and Characterization:
3-O-Benzyl-beta-D-glucose can be synthesized from glucose in several ways. One of the most common methods is the reaction of glucose with benzyl alcohol in the presence of a dehydrating agent such as sulfuric acid. The reaction produces 3-O-Benzyl-beta-D-glucose and water. Another method is the acid-catalyzed reaction of glucose with benzyl chloride in the presence of a base such as sodium hydroxide.
Characterization of 3-O-Benzyl-beta-D-glucose can be achieved by various techniques such as nuclear magnetic resonance (NMR) spectroscopy, infrared (IR) spectroscopy, mass spectrometry, and X-ray crystallography. NMR spectroscopy is the most commonly used technique for the characterization of 3-O-Benzyl-beta-D-glucose. The NMR spectrum of the compound shows characteristic signals for the glucose moiety and the benzyl group.
Analytical Methods:
Analytical methods such as high-performance liquid chromatography (HPLC) and gas chromatography (GC) can be used to analyze 3-O-Benzyl-beta-D-glucose. HPLC is the most common method used for the analysis of 3-O-Benzyl-beta-D-glucose because it offers high sensitivity and resolution. It is also used to separate and quantify other impurities present in the sample.
Biological Properties:
3-O-Benzyl-beta-D-glucose has shown various biological properties such as antitumor and antioxidant activities. It has been reported to inhibit the growth of various cancer cell lines such as human leukemia cells and hepatoma cells. Additionally, 3-O-Benzyl-beta-D-glucose has exhibited a strong antioxidant activity by scavenging free radicals and reducing lipid peroxidation.
Toxicity and Safety in Scientific Experiments:
Studies have reported that 3-O-Benzyl-beta-D-glucose is relatively safe at low concentrations. However, at higher concentrations, it has shown cytotoxicity towards cancer cells and various organ cells, including liver cells. Therefore, it is essential to conduct toxicity studies before using 3-O-Benzyl-beta-D-glucose in scientific experiments.
Applications in Scientific Experiments:
3-O-Benzyl-beta-D-glucose has various applications in scientific experiments. It is commonly used as a starting material to synthesize various bioactive molecules. It is also used as a ligand in metal catalysis and chiral organic synthesis.
Current State of Research:
There is ongoing research in the field of 3-O-Benzyl-beta-D-glucose. Several studies have focused on its potential anticancer and antioxidant activities. Others have examined its use as a starting material to synthesize various bioactive molecules.
Potential Implications in Various Fields of Research and Industry:
3-O-Benzyl-beta-D-glucose has potential implications in various fields of research and industry. It can be used as a starting material to synthesize various bioactive molecules for use in pharmaceuticals. It can also be used as a ligand in metal catalysis and chiral organic synthesis.
Limitations and Future Directions:
Despite its biological and chemical properties, 3-O-Benzyl-beta-D-glucose has limitations. It is relatively expensive to produce, and its use is limited to scientific experimentation. Additionally, there is a lack of information regarding its potential toxicity. Further research is needed to determine its full potential in various fields of research and industry.
Future directions for research on 3-O-Benzyl-beta-D-glucose include: finding more efficient and cost-effective methods for its synthesis, conducting toxicology studies to determine its toxicity levels, investigating its potential as a drug target for the treatment of cancer, and exploring its applications as a ligand in metal catalysis and chiral organic synthesis.
Conclusion:
3-O-Benzyl-beta-D-glucose is a chemical compound with various physical, chemical, and biological properties. It has potential applications in various fields of research and industry, including as a starting material to synthesize bioactive molecules and a ligand in metal catalysis and chiral organic synthesis. However, further research is needed to determine its full potential and limitations.
CAS Number | 10230-17-8 |
Product Name | 3-O-Benzyl-beta-D-glucose |
IUPAC Name | (2R,3R,4S,5R,6R)-6-(hydroxymethyl)-4-phenylmethoxyoxane-2,3,5-triol |
Molecular Formula | C13H18O6 |
Molecular Weight | 270.28 |
InChI | InChI=1S/C13H18O6/c14-6-9-10(15)12(11(16)13(17)19-9)18-7-8-4-2-1-3-5-8/h1-5,9-17H,6-7H2/t9-,10-,11-,12+,13-/m1/s1 |
SMILES | C1=CC=C(C=C1)COC2C(C(OC(C2O)O)CO)O |
CAS No: 10230-17-8 MDL No: MFCD00051212 Chemical Formula: C13H18O6 Molecular Weight: 270.28 |
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