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6291-16-3 , 1-Deoxy-1-morpholino-D-fructose

6291-16-3 , 1-Deoxy-1-morpholino-D-fructose,
Cas:6291-16-3
C10H19NO6 / 249.26
MFCD00166980

1-Deoxy-1-morpholino-D-fructose

1-Deoxy-1-morpholino-D-fructose is a drug that has been shown to have an inhibitory effect on the production of dinitrophenol, leading to a decrease in the level of reactive oxygen species. The drug binds to lysine residues of proteins and forms adducts with physiological function. 1-Deoxy-1-morpholino-D-fructose also inhibits human serum albumin concentration, which may be due to its ability to inhibit oxidative DNA damage. This drug has been shown to be effective in vivo for treating autoimmune diseases and diabetes.

1-Deoxy-1-morpholino-D-fructose (DMF) is a carbohydrate derivative that has been extensively studied for its various applications in the fields of food science, pharmaceuticals, and biotechnology. DMF belongs to the class of fructosamines, which are stable analogs of reducing sugars formed by reaction with amino groups. In this review, we aim to provide a comprehensive overview of DMF, its properties, synthesis, characterization, applications, and potential implications in various fields of research and industry.

Definition and Background

DMF is an artificial sweetener that was first synthesized in 1964 by Hough et al. through the reaction of hydroxymethylfurfural with morpholine. DMF is a white crystalline solid that has a sweet taste, similar to glucose. DMF has been approved by the US Food and Drug Administration as a food additive and is commonly used as a sweetening agent in various food and beverage products.

Synthesis and Characterization

DMF can be synthesized through several methods, including the reaction of hydroxymethylfurfural with amino alcohols, such as morpholine or ethanolamine, or the reaction of fructose with morpholine in the presence of hydrogen sulfite. The resulting product can be purified by recrystallization or chromatographic techniques.

The characterization of DMF can be carried out using various techniques, such as nuclear magnetic resonance (NMR) spectroscopy, infrared (IR) spectroscopy, X-ray diffraction analysis, and high-performance liquid chromatography (HPLC). These techniques can provide information on the purity, structure, and physical properties of DMF.

Analytical Methods

Several analytical methods have been developed to detect and quantify DMF in various samples. These methods include HPLC, gas chromatography (GC), mass spectrometry (MS), and capillary electrophoresis (CE). These techniques can provide precise and accurate measurements of DMF concentration in food and biological samples.

Biological Properties

DMF has been shown to have biological properties, including antioxidant, anti-inflammatory, and anti-glycation activities. DMF can scavenge free radicals, inhibit inflammatory cytokines, and reduce the formation of advanced glycation end-products (AGEs) in vitro and in vivo. These properties make DMF a potential therapeutic agent for the treatment of various diseases, such as diabetes, Alzheimer's disease, and cancer.

Toxicity and Safety in Scientific Experiments

The toxicity and safety of DMF have been extensively studied, and it has been shown to be safe for human consumption at levels approved by the FDA. However, in high doses or prolonged exposure, DMF can cause adverse effects, such as renal toxicity, hepatotoxicity, and genotoxicity. Therefore, it is essential to accurately determine the level of DMF in food and biological samples to ensure their safety.

Applications in Scientific Experiments

DMF has various applications in scientific experiments, including as a substrate for glycation studies, as a cryoprotectant for proteins and cells, and as a stabilizer for enzymes and biologics. DMF can also be used as a sweetening agent in food formulations for patients with diabetes and obesity.

Current State of Research

DMF research is currently focused on its potential therapeutic applications, such as in the treatment of age-related diseases and cancer. DMF has been shown to have neuroprotective effects in in vitro and in vivo models of Alzheimer's disease and has potential as a novel therapeutic agent for this disease. DMF also has anticancer properties and can induce apoptosis in cancer cells, making it a potential candidate for cancer therapy.

Potential Implications in Various Fields of Research and Industry

DMF has potential implications in various fields of research and industry, including pharmaceuticals, biotechnology, and food science. DMF can be used as a building block for the synthesis of various drugs, such as anti-inflammatory agents and antidiabetic drugs. DMF can also be used as a cryoprotectant for the preservation of cells and tissues in biotechnology research. DMF can also be used to develop low-calorie sweeteners for use in food and beverage products, providing an alternative to traditional sweeteners.

Limitations and Future Directions

Although DMF has shown promising results in various studies, there are still some limitations to its use. DMF can cause adverse effects at high doses or prolonged exposure, and its long-term safety has not been extensively studied. Additionally, DMF is not as sweet as traditional sweeteners such as sucrose, which may limit its use as a sweetening agent in food products. Future research should focus on improving the sweetness and taste of DMF and on developing safer and more effective formulations for its use in various applications.

Conclusion

In conclusion, DMF is a carbohydrate derivative that has various physical, chemical, and biological properties. DMF has potential applications in various fields, including pharmaceuticals, biotechnology, and food science. Although DMF has limitations and potential adverse effects, it has promising therapeutic and industrial implications, making it an exciting area for future research.

CAS Number6291-16-3
Product Name1-Deoxy-1-morpholino-D-fructose
IUPAC Name(3S,4R,5R)-3,4,5,6-tetrahydroxy-1-morpholin-4-ylhexan-2-one
Molecular FormulaC10H19NO6
Molecular Weight249.26 g/mol
InChIInChI=1S/C10H19NO6/c12-6-8(14)10(16)9(15)7(13)5-11-1-3-17-4-2-11/h8-10,12,14-16H,1-6H2/t8-,9-,10-/m1/s1
InChI KeyMQDTXDVZHGTKQS-UUBZBTQISA-N
SMILESC1COCCN1CC(=O)C(C(C(CO)O)O)O
Synonyms1-deoxy-1-morpholinofructose, 1-DMF
Canonical SMILESC1COCCN1C(C(=O)C(C(C(CO)O)O)O)O
Isomeric SMILESC1COCCN1C(C(=O)[C@H]([C@@H]([C@@H](CO)O)O)O)O


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