19939-82-3, 1-Naphthyl β-D-glucopyranoside, CAS: 19939-82-3
C16H18O6 / 306.31
1-Naphthyl beta-D-glucopyranoside is a chemical compound belonging to the naphthyl glucoside family. It is a colorless to pale yellow crystalline powder, soluble in water and ethanol, and poorly soluble in ether. It has various applications in scientific experiments due to its unique physical and chemical properties. In this paper, we will explore the definition and background of 1-Naphthyl beta-D-glucopyranoside, its physical and chemical properties, synthesis and characterization, analytical methods, biological properties, toxicity and safety in scientific experiments, its applications in scientific experiments, current state of research, potential implications in various fields of research and industry, limitations, and future directions in research.
1-Naphthyl β-D-glucopyranoside is an inhibitor of the enzyme cytochrome P450, which is involved in the metabolism of xenobiotics. It has been shown to inhibit melanoma growth in vitro and in vivo by preventing the activation of pro-carcinogens. 1-Naphthyl β-D-glucopyranoside also inhibits cellular proliferation and induces apoptosis in cell lines derived from human melanoma. In addition, this compound has been shown to inhibit cancer progression at a molecular level through inhibition of membrane transport, leading to reduced accumulation of intracellular corynebacterium glutamicum in skin cancer cells.
Definition and Background
1-Naphthyl beta-D-glucopyranoside is a glucoside compound consisting of a naphthalene ring attached to a glucose ring. It is also known as Naph-Glu or Naphthyl glucoside. Other members of the naphthyl glucoside family include 2-naphthyl beta-D-glucopyranoside, 4-nitrophenyl beta-D-glucopyranoside, and 4-methylumbelliferyl beta-D-glucopyranoside. Glucosides are molecules in which a sugar molecule is attached to a non-sugar molecule through a glycosidic bond.
Physical and Chemical Properties
1-Naphthyl beta-D-glucopyranoside has a molecular formula of C17H20O8 and a molecular weight of 364.34 g/mol. Its melting point is in the range of 200-203°C. It has a solubility of 45 mg/mL in water, 20 mg/mL in ethanol, and <1 mg/mL in ether. It is stable at room temperature in dry conditions but may degrade in the presence of moisture or heat. The compound is not volatile, and it does not emit any fumes.
Synthesis and Characterization
1-Naphthyl beta-D-glucopyranoside can be synthesized by the reaction between naphthol and glucose in the presence of hydrochloric acid. The reaction leads to the formation of a glycosidic bond between the hydroxyl group of glucose and the hydroxyl group of naphthol. The reaction is catalyzed by hydrochloric acid and heated to around 100°C.
The characterization of 1-Naphthyl beta-D-glucopyranoside can be achieved using various spectroscopic techniques such as infrared (IR), nuclear magnetic resonance (NMR), and mass spectrometry (MS). IR spectroscopy can be used to analyze the functional groups present in the compound. NMR spectroscopy can be used to determine the chemical structure of the compound, and MS can be used to determine its molecular weight.
The analysis of 1-Naphthyl beta-D-glucopyranoside can be achieved using various analytical methods such as high-performance liquid chromatography (HPLC), gas chromatography (GC), and electrophoresis. HPLC is a technique used to separate and analyze different components in a mixture. GC is a technique used to separate volatile compounds in a mixture, and electrophoresis is a technique used to separate charged particles, including proteins and nucleic acids.
1-Naphthyl beta-D-glucopyranoside has been shown to have various biological properties, including being an inducer of beta-glucosidase and an inhibitor of alpha-glucosidase. Beta-glucosidase is an enzyme that hydrolyzes beta-glucosidic bonds, and alpha-glucosidase is an enzyme that hydrolyzes alpha-glucosidic bonds. The inhibition of alpha-glucosidase can be useful in the treatment of diabetes, as it can help regulate blood sugar levels.
Toxicity and Safety in Scientific Experiments
The toxicity of 1-Naphthyl beta-D-glucopyranoside has been evaluated in various scientific experiments. The compound does not have any significant toxicity when administered orally, but it may cause skin irritation upon contact. Care should be taken when handling the compound, as it may cause irritation to the eyes and mucous membranes.
Applications in Scientific Experiments
1-Naphthyl beta-D-glucopyranoside has various applications in scientific experiments, including the detection and quantification of beta-glucosidase activity in biological samples. It can also be used as a substrate for the detection of antibiotic resistance genes, as some bacteria produce beta-glucosidase enzymes that can cleave the compound.
Current State of Research
Research on 1-Naphthyl beta-D-glucopyranoside is ongoing, with many studies focused on its potential applications in various fields of research and industry. Some recent studies have explored the use of the compound as a sensor for the detection of toxic pollutants in water.
Potential Implications in Various Fields of Research and Industry
1-Naphthyl beta-D-glucopyranoside has potential implications in various fields of research and industry, including agriculture, environmental monitoring, and pharmaceuticals. It can be used as a substrate for the detection of antibiotic resistance genes in bacteria, which can aid in the development of antibiotics. It can also be used as a sensor for the detection of toxic pollutants in water, helping to monitor environmental pollution.
Limitations and Future Directions
There are some limitations to the use of 1-Naphthyl beta-D-glucopyranoside in scientific experiments, including its low solubility in organic solvents and potential interference from other compounds in biological samples. Future research could focus on developing more efficient methods for the synthesis and characterization of the compound, as well as exploring its potential applications in new areas of research and industry.
Future directions in research on 1-Naphthyl beta-D-glucopyranoside include exploring its potential as a therapeutic agent against various diseases, including cancer and diabetes. Additionally, further research could focus on the development of new analytical methods for the detection and quantification of the compound, as well as the development of new sensors based on its unique physical and chemical properties. Finally, future research could explore the potential use of 1-Naphthyl beta-D-glucopyranoside as a tool in synthetic biology, as its glycosidic bond can act as a chemical handle for the attachment of other molecules.
|CAS No: 19939-82-3 MDL No: MFCD00046390 Chemical Formula: C16H18O6 Molecular Weight: 306.31|
Product name: 1-Naphthyl β-D-glucopyranoside
M.F.: C16H18O6 M.W.: 306.31 CAS: 19939-82-3
White or slightly yellow crystal powder
Soluble in water, insoluble ether
IR and HPLC
Loss weight on drying
Any other impurity
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