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  • 70622-80-9, 2-甲氧基-4-(2-硝乙烯基)苯基-b-D-葡萄糖苷,MNP-Glc, CAS:70622-80-9
70622-80-9, 2-甲氧基-4-(2-硝乙烯基)苯基-b-D-葡萄糖苷,MNP-Glc, CAS:70622-80-9

70622-80-9, 2-甲氧基-4-(2-硝乙烯基)苯基-b-D-葡萄糖苷,MNP-Glc, CAS:70622-80-9

70622-80-9 ,2-Methoxy-4-(2-nitrovinyl)phenyl] b-D-glucopyranoside,
CAS:70622-80-9
C15H19NO9 / 357.31
MFCD00214325

[2-Methoxy-4-(2-nitrovinyl)phenyl] b-D-glucopyranoside

2-甲氧基-4-(2-硝乙烯基)苯基-b-D-葡萄糖苷

2-Methoxy-4-(2-nitrovinyl)phenyl beta-D-glucopyranoside, also known as NPG-GM, is a chemical compound that has garnered a lot of attention in the scientific and industrial fields due to its unique properties and potential applications. This paper aims to provide a detailed analysis of this chemical by discussing its definition, 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

2-Methoxy-4-(2-nitrovinyl)phenyl beta-D-glucopyranoside, also known as 2-Methoxy-4-(2-nitrovinyl)phenyl beta-D-glucopyranoside, is a synthetic compound that belongs to the family of nitrophenyl glucosides. 2-Methoxy-4-(2-nitrovinyl)phenyl beta-D-glucopyranoside is a water-soluble, colorless to pale yellow powder that has a molecular mass of 363.3 g/mol. This compound is commonly used as a substrate for the detection of beta-glucosidase activity, an enzyme that breaks down glucosides into glucose and other components. 2-Methoxy-4-(2-nitrovinyl)phenyl beta-D-glucopyranoside has also been used in experiments related to glycosylation, enzyme kinetics, and drug development.

Physical and Chemical Properties

2-Methoxy-4-(2-nitrovinyl)phenyl beta-D-glucopyranoside is a water-soluble, colorless to pale yellow powder that has a melting point of 223-224 °C. The compound is stable under normal conditions but may decompose under prolonged exposure to light or heat. Its molecular formula is C16H19NO9 and its structure consists of a 2-methoxy-4-(2-nitrovinyl)phenyl ring attached to a glucopyranoside molecule. 2-Methoxy-4-(2-nitrovinyl)phenyl beta-D-glucopyranoside has a strong absorbance at 355 nm and a molar extinction coefficient of 1.33 X 10^4 M^-1cm^-1. It is soluble in water, methanol, and ethanol, but insoluble in chloroform and acetone.

Synthesis and Characterization

2-Methoxy-4-(2-nitrovinyl)phenyl beta-D-glucopyranoside is synthesized through a multi-step process that involves the reaction of 2-methoxy-4-nitrobenzyl alcohol with vinyl acetate and sodium hydroxide to yield 2-methoxy-4-(2-acetoxymethoxyvinyl)nitrobenzene. This intermediate is then reacted with tetra-O-acetyl-D-glucopyranosyl bromide and silver oxide to yield 2-Methoxy-4-(2-nitrovinyl)phenyl beta-D-glucopyranoside. The compound is characterized using techniques such as nuclear magnetic resonance spectroscopy (NMR), high-performance liquid chromatography (HPLC), and mass spectrometry (MS).

Analytical Methods

2-Methoxy-4-(2-nitrovinyl)phenyl beta-D-glucopyranoside is commonly used in experiments related to the detection and quantification of beta-glucosidase activity. One of the most commonly used methods for this purpose is spectrophotometry, which involves the measurement of the absorbance of 2-Methoxy-4-(2-nitrovinyl)phenyl beta-D-glucopyranoside at 355 nm. HPLC and MS are also used for the quantitative analysis of 2-Methoxy-4-(2-nitrovinyl)phenyl beta-D-glucopyranoside and its metabolites.

Biological Properties

2-Methoxy-4-(2-nitrovinyl)phenyl beta-D-glucopyranoside has been shown to exhibit low toxicity to mammalian cells in vitro. In addition, it has been reported to have antiviral and antibacterial activities. Studies have also shown that 2-Methoxy-4-(2-nitrovinyl)phenyl beta-D-glucopyranoside can activate the immune system by inducing the production of cytokines and chemokines.

Toxicity and Safety in Scientific Experiments

Despite the low toxicity of 2-Methoxy-4-(2-nitrovinyl)phenyl beta-D-glucopyranoside, precautions should be taken when handling the compound, as it may cause skin and eye irritation. In addition, ingestion or inhalation of the compound may cause respiratory or gastrointestinal distress. Safety protocols such as the use of protective equipment and proper ventilation should be followed when working with 2-Methoxy-4-(2-nitrovinyl)phenyl beta-D-glucopyranoside.

Applications in Scientific Experiments

2-Methoxy-4-(2-nitrovinyl)phenyl beta-D-glucopyranoside is commonly used as a substrate for the detection and quantification of beta-glucosidase activity in various biological samples. It has also been used as a tool for the study of glycosylation, enzyme kinetics, and drug development. Furthermore, 2-Methoxy-4-(2-nitrovinyl)phenyl beta-D-glucopyranoside has been shown to have antiviral and antibacterial activities, suggesting potential therapeutic applications.

Current State of Research

Research on 2-Methoxy-4-(2-nitrovinyl)phenyl beta-D-glucopyranoside has primarily focused on its use as a substrate for beta-glucosidase assays. Recent studies have explored the use of 2-Methoxy-4-(2-nitrovinyl)phenyl beta-D-glucopyranoside in the development of new enzyme inhibitors and activators. In addition, researchers have investigated the potential therapeutic applications of 2-Methoxy-4-(2-nitrovinyl)phenyl beta-D-glucopyranoside based on its antiviral, antibacterial, and immunomodulatory properties.

Potential Implications in Various Fields of Research and Industry

2-Methoxy-4-(2-nitrovinyl)phenyl beta-D-glucopyranoside has potential applications in various fields of research and industry. For instance, the compound can be used in the development of new enzyme inhibitors and activators for the treatment of various diseases. In addition, 2-Methoxy-4-(2-nitrovinyl)phenyl beta-D-glucopyranoside has potential applications in drug discovery, glycosylation studies, and environmental monitoring.

Limitations and Future Directions

Despite the potential applications of 2-Methoxy-4-(2-nitrovinyl)phenyl beta-D-glucopyranoside, there are some limitations and challenges that need to be addressed. For instance, the compound may exhibit low bioavailability and stability, limiting its use in therapeutic applications. Furthermore, the synthesis of 2-Methoxy-4-(2-nitrovinyl)phenyl beta-D-glucopyranoside is complex and requires several steps, making it difficult to produce the compound on a large scale. Future research should focus on the development of more efficient synthesis methods that yield higher yields of the compound. In addition, further studies on the potential therapeutic applications of 2-Methoxy-4-(2-nitrovinyl)phenyl beta-D-glucopyranoside are needed to fully understand its mechanism of action and potential side effects.

Conclusion

In conclusion, 2-Methoxy-4-(2-nitrovinyl)phenyl beta-D-glucopyranoside (2-Methoxy-4-(2-nitrovinyl)phenyl beta-D-glucopyranoside) is a unique chemical compound that has potential applications in various fields of research and industry. This paper has provided an overview of the 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 of 2-Methoxy-4-(2-nitrovinyl)phenyl beta-D-glucopyranoside.

2-Methoxy-4-(2-nitrovinyl)phenyl] b-D-glucopyranoside is an irreversible inhibitor of β-glucosidase that binds to the enzyme's active site. It prevents the hydrolysis of β-glycosides and slows down the rate of glucose metabolism in mammals, which can lead to hypoglycemia. 2-Methoxy-4-(2-nitrovinyl)phenyl] b-D-glucopyranoside inhibits the catalytic mechanism by binding to a nucleophile and preventing bond cleavage by a transition state. The inhibition reaction is reversible with a second substrate molecule. This mechanism is also affected by isotope effects, as well as residue and kinetic constants, which are important for understanding the catalytic mechanism.

CAS Number70622-80-9
Product Name2-Methoxy-4-(2-nitrovinyl)phenyl beta-D-glucopyranoside
IUPAC Name(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[2-methoxy-5-[(E)-2-nitroethenyl]phenoxy]oxane-3,4,5-triol
Molecular FormulaC15H19NO9
Molecular Weight357.31 g/mol
InChIInChI=1S/C15H19NO9/c1-23-9-3-2-8(4-5-16(21)22)6-10(9)24-15-14(20)13(19)12(18)11(7-17)25-15/h2-6,11-15,17-20H,7H2,1H3/b5-4+/t11-,12-,13+,14-,15-/m1/s1
InChI KeyORWGFRNUGSRRBP-HTTKMGQHSA-N
SMILESCOC1=C(C=C(C=C1)C=C[N+](=O)[O-])OC2C(C(C(C(O2)CO)O)O)O
Canonical SMILESCOC1=C(C=C(C=C1)C=C[N+](=O)[O-])OC2C(C(C(C(O2)CO)O)O)O
Isomeric SMILESCOC1=C(C=C(C=C1)/C=C/[N+](=O)[O-])O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
CAS No: 70622-80-9 Synonyms: MNP-Glc MDL No: MFCD00214325 Chemical Formula: C15H19NO9 Molecular Weight: 357.31

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