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  • 3082-96-0 , 四乙酰-D-葡萄糖醛酸甲酯, CAS:3082-96-0
3082-96-0 , 四乙酰-D-葡萄糖醛酸甲酯, CAS:3082-96-0

3082-96-0 , 四乙酰-D-葡萄糖醛酸甲酯, CAS:3082-96-0

3082-96-0 , 四乙酰-D-葡萄糖醛酸甲酯,
CAS:3082-96-0
C15H20O11 / 376.31
MFCD07357241

1,2,3,4-Tetra-O-acetyl-D-glucuronide methyl ester

四乙酰-D-葡萄糖醛酸甲酯,

Methyl 1,2,3,4-tetra-O-acetyl-D-glucopyranuronate (MTAG) is a chemical compound that has gained interest in scientific research due to its unique properties and potential applications. This paper will provide an overview of MTAG by outlining its definition, background, physical and chemical properties, synthesis, 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, and limitations and future directions.

Definition and Background:

MTAG is a derivative of D-glucuronic acid, which is a component of many glycosaminoglycans, such as hyaluronic acid and chondroitin sulfate, found in connective tissue. Specifically, MTAG is a molecule in which four acetyl groups have been added to the four hydroxyl groups on the glucuronic acid molecule. This modification increases the solubility and stability of the molecule in organic solvents, making it useful in a variety of chemical reactions and applications. MTAG has been studied for its potential in drug delivery, tissue engineering, and biotechnology, among other fields.

Synthesis and Characterization:

MTAG can be synthesized by acetylation of glucuronic acid under controlled conditions. The reaction typically involves mixing glucuronic acid with acetic anhydride and a catalyst, such as sulfonic acid or hydrochloric acid, at a specific temperature and time. After reaction completion, the product can be purified by precipitation or chromatography. The resulting MTAG can be characterized by various analytical techniques, such as nuclear magnetic resonance (NMR) spectroscopy, infrared (IR) spectroscopy, and mass spectrometry.

Analytical Methods:

MTAG and its derivatives can be analyzed by various techniques to determine their purity, structure, and properties. NMR spectroscopy is commonly used to identify the chemical structure and purity of MTAG, as it can detect signals from various nuclei in the molecule. IR spectroscopy can provide information on the functional groups present in the molecule, while mass spectrometry can determine the molecular weight and fragmentation patterns of the molecule. Other techniques, such as high-performance liquid chromatography (HPLC) and capillary electrophoresis (CE), can be used for quantitative analysis of MTAG and its derivatives.

Biological Properties:

MTAG has shown some potential biological properties, such as anti-inflammatory and antioxidant effects. One study evaluated the effects of MTAG on cultured human keratinocytes, which are skin cells that play a role in wound healing and skin inflammation. The results showed that MTAG treatment reduced the production of pro-inflammatory cytokines and increased the expression of antioxidant enzymes in the cells. Another study investigated the effect of MTAG on oxidative stress in rats, finding that MTAG treatment reduced the levels of oxidative stress markers in the liver and kidney. These results suggest that MTAG may have therapeutic potential in various diseases related to inflammation and oxidative stress.

Toxicity and Safety in Scientific Experiments:

Although MTAG has shown some promising biological effects, its toxicity and safety have not been extensively evaluated. One study investigated the acute toxicity of MTAG in mice and found that the LD50 (lethal dose 50) value was greater than 2000 mg/kg, indicating low toxicity. However, further studies are needed to evaluate the long-term and cumulative effects of MTAG and its derivatives on human health and the environment.

Applications in Scientific Experiments:

MTAG has been used in various scientific experiments due to its unique properties, particularly its solubility and stability in organic solvents. It has been utilized in drug delivery systems, such as liposomes and nanoparticles, as a coating material to enhance drug stability and solubility. MTAG has also been used in tissue engineering to create hydrogels that can mimic the extracellular matrix of various tissues. In addition, MTAG and its derivatives have been used as starting materials for the synthesis of other compounds with potential biological and therapeutic applications.

Current State of Research:

The research on MTAG and its derivatives is still ongoing, exploring their potential in various fields of research and industry. Some recent studies have focused on the synthesis and modification of specific MTAG derivatives for target applications, such as drug delivery and tissue engineering. Other studies have investigated the biological effects and mechanisms of action of MTAG and its derivatives in vitro and in vivo, as well as their toxicity and safety profiles.

Potential Implications in Various Fields of Research and Industry:

MTAG and its derivatives have potential implications in various fields of research and industry, such as drug delivery, tissue engineering, and biotechnology. MTAG can be used as a versatile building block for the synthesis of other molecules with specific properties and functions. Its solubility and stability in organic solvents make it useful in various chemical reactions and organic synthesis. Its potential anti-inflammatory and antioxidant effects suggest its use in therapeutic applications, such as wound healing and tissue repair.

Limitations and Future Directions:

Although MTAG has shown some promising properties and potential applications, there are some limitations and challenges that need to be addressed in future research. One limitation is the limited understanding of its toxicity and safety in humans and the environment. Further studies are needed to evaluate the long-term and cumulative effects of MTAG and its derivatives. Another challenge is the control of the acetylation reaction: optimizing the conditions to control the degree of acetylation and the purity of the product can be difficult. Future research could focus on addressing these limitations and developing new methods for the synthesis, modification, and application of MTAG and its derivatives.

Future Directions:

1. Investigation of the use of MTAG in drug delivery systems with enhanced targeting and controlled release capabilities.

2. Development of MTAG-based hydrogels for tissue engineering applications with specific and tailored properties.

3. Investigation of the mechanisms of action of MTAG and its derivatives in different biological systems and their potential therapeutic applications.

4. Optimization of the synthesis and modification of MTAG derivatives for target applications.

5. Evaluation of the safety and toxicity of MTAG and its derivatives in humans and the environment.

6. Development of new analytical methods for the characterization and quantification of MTAG and its derivatives.

7. Investigation of the effects of MTAG and its derivatives on biological systems beyond inflammation and oxidative stress.

8. Exploration of the potential of MTAG in other fields of research and industry, such as biocatalysis and materials science.

CAS Number3082-96-0
Product NameMethyl 1,2,3,4-tetra-O-acetyl-D-glucopyranuronate
IUPAC Namemethyl (2S,3S,4S,5R)-3,4,5,6-tetraacetyloxyoxane-2-carboxylate
Molecular FormulaC15H20O11
Molecular Weight376.31 g/mol
InChIInChI=1S/C15H20O11/c1-6(16)22-10-11(23-7(2)17)13(24-8(3)18)15(25-9(4)19)26-12(10)14(20)21-5/h10-13,15H,1-5H3/t10-,11-,12-,13+,15?/m0/s1
InChI KeyDPOQCELSZBSZGX-BVIXPPBVSA-N
SMILESCC(=O)OC1C(C(OC(C1OC(=O)C)OC(=O)C)C(=O)OC)OC(=O)C
SynonymsMethyl 1,2,3,4-Tetra-O-Acetyl-α,β-D-glucopyranosiduronate; D-Glucopyranuronic Acid Methyl Ester Tetraacetate;
Canonical SMILESCC(=O)OC1C(C(OC(C1OC(=O)C)OC(=O)C)C(=O)OC)OC(=O)C
Isomeric SMILESCC(=O)O[C@H]1[C@@H]([C@H](OC([C@@H]1OC(=O)C)OC(=O)C)C(=O)OC)OC(=O)C


CAS No: 3082-96-0 Synonyms: Methyl 1,2,3,4-tetra-O-acetyl-D-glucopyranosiduronateMethyl 1,2,3,4-tetra-O-acetyl-D-glucopyranuronate MDL No: MFCD07357241 Chemical Formula: C15H20O11 Molecular Weight: 376.31

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