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492-30-8 ,2-C-methyl-d-ribono-1,4-lactone;3,4-dihydroxy-5-(hydroxymethyl)-3-methyloxolan-2-one,CAS:492-30-8

492-30-8 ,2-C-methyl-d-ribono-1,4-lactone;3,4-dihydroxy-5-(hydroxymethyl)-3-methyloxolan-2-one,
CAS:492-30-8
C6H10O5 / 162.14
MFCD07369541

2-C-Methyl-D-ribono-1,4-lactone

2-C-甲基-D-核糖酸-1,4-内酯

2-C-Methyl-D-ribono-1,4-lactone is a ketose which is formed from the thermal rearrangement of d-xylose. It has been shown to be an acceptor for episulfide and an 1-deoxy-d-ribulose. 2-C-Methyl-D-ribono-1,4-lactone has been found to yield dimethylamine when heated with magnesium. This compound can be ion exchanged with calcium and magnesium. 2CMR was first synthesized by the reaction of L(+) lactic acid with dimethylamine in the presence of magnesium chloride. The product was purified by crystallization from water, yielding a white powder that melts at 230°C.

(3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one, also known as D-mannitol, is a six-carbon sugar alcohol and a common sugar substitute. It is naturally occurring in some fruits and vegetables but is mainly produced through the hydrogenation of fructose or glucose. D-mannitol has a wide range of applications in the pharmaceutical, food, and chemical industries due to its excellent physical and chemical properties and low toxicity. In this paper, we will review the 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 D-mannitol.

Synthesis and Characterization

(3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one can be synthesized through various methods, such as hydrogenation of fructose or glucose, catalytic hydrogenation of methyl D-gluconate, and isomerization of D-glucose. The most common method is the hydrogenation of fructose or glucose, which involves the use of a catalyst such as nickel, platinum, or palladium in the presence of hydrogen gas at high pressure and temperature. The resulting product is then purified to obtain pure (3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one.

The characterization of (3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one can be done through various techniques such as nuclear magnetic resonance (NMR) spectroscopy, Fourier transform-infrared (FT-IR) spectroscopy, X-ray diffraction (XRD), and differential scanning calorimetry (DSC). NMR spectroscopy can be used to identify the structure and purity of (3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one, while FT-IR spectroscopy can be used to determine the functional groups present in the compound. X-ray diffraction and DSC can be used to analyze the crystal structure and thermal behavior of (3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one.

Analytical Methods

Various analytical methods can be used to quantify (3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one in different matrices such as food, pharmaceuticals, and biological samples. These methods include high-performance liquid chromatography (HPLC), gas chromatography (GC), capillary electrophoresis (CE), and enzyme-based methods. HPLC is the most common method used for the quantification of (3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one in pharmaceuticals, while GC is used for the analysis of (3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one in food samples.

Biological Properties

(3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one has low toxicity and is considered safe for consumption by humans. It is commonly used as a sugar substitute in food products due to its low calorie content and lack of adverse effects on blood glucose levels. (3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one has also been shown to have antioxidant and anti-inflammatory properties, which make it a promising candidate for the prevention and treatment of various diseases such as diabetes, neurodegenerative disorders, and cancer.

Toxicity and Safety in Scientific Experiments

(3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one has been extensively studied for its toxicity and safety in scientific experiments. Studies have shown that (3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one has low acute toxicity and does not cause significant adverse effects on animal models when administered in high doses. However, long-term exposure to (3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one may cause mild gastrointestinal disturbances such as diarrhea and abdominal pain. Therefore, it is important to use appropriate doses and monitor the potential side effects of (3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one in scientific experiments.

Applications in Scientific Experiments

(3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one has a wide range of applications in scientific experiments. It is commonly used as a cryoprotectant in the preservation of biological samples such as cells, tissues, and organs. (3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one can also be used as a stabilizer for proteins and enzymes, as well as a bulking agent in the formulation of pharmaceuticals. In addition, (3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one can be used as a substrate for the production of various enzymes such as mannitol dehydrogenase, which has applications in biocatalysis.

Current State of Research

Research on (3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one has been mainly focused on its applications in the pharmaceutical, food, and chemical industries. Recent studies have shown that (3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one has potential as a therapeutic agent for the prevention and treatment of various diseases such as diabetes, Alzheimer's disease, and cancer. In addition, research on the synthesis and characterization of (3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one has led to the development of new methods for the production of high-purity (3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one and its derivatives.

Potential Implications in Various Fields of Research and Industry

(3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one has various potential implications in different fields of research and industry. In the pharmaceutical industry, (3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one can be used as a bulking agent and stabilizer for the formulation of drugs. It can also be used as a cryoprotectant for the preservation of biological samples in research and clinical settings. In the food industry, (3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one can be used as a sugar substitute and an additive for the formulation of low-calorie and low-sugar foods. In the chemical industry, (3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one can be used as a starting material for the production of various chemicals and materials such as surfactants, resins, and adhesives.

Limitations and Future Directions

Despite its promising potential in various fields of research and industry, the use of (3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one has several limitations. One of the main limitations is its high production cost, which hinders its widespread use in some applications. In addition, the stability of (3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one in some formulations and matrices needs to be further studied to optimize its performance and shelf-life. Further research on the mechanisms of action and therapeutic potential of (3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one is also needed to identify new targets and applications in different diseases.

Future directions for research on (3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one include the development of new methods for the synthesis and purification of (3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one and its derivatives, the exploration of its potential as a therapeutic agent in different diseases, and the optimization of its performance in different applications. In addition, the safety and toxicity of (3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one in humans need to be further studied to ensure its safe use in pharmaceuticals and other applications.

CAS Number492-30-8
Product Name(3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one
IUPAC Name(3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyloxolan-2-one
Molecular FormulaC6H10O5
Molecular Weight162.14 g/mol
InChIInChI=1S/C6H10O5/c1-6(10)4(8)3(2-7)11-5(6)9/h3-4,7-8,10H,2H2,1H3/t3-,4-,6-/m1/s1
InChI KeyWJBVKNHJSHYNHO-ZMIZWQJLSA-N
SMILESCC1(C(C(OC1=O)CO)O)O
Synonyms2-C-Methyl-D-ribonic Acid γ-Lactone; 2-C-Methyl-D-ribo-pentonic Acid γ-Lactone; NSC 19768; NSC 62382; α-D-Glucosaccharinic Acid γ-Lactone;
Canonical SMILESCC1(C(C(OC1=O)CO)O)O
Isomeric SMILESC[C@]1([C@@H]([C@H](OC1=O)CO)O)O
CAS No: 492-30-8 MDL No: MFCD07369541 Chemical Formula: C6H10O5 Molecular Weight: 162.14white to off-white crystalline powder.
References: 1. Lopez-Herrera FJ, Sarabia-Garcia F, et al., J. Carbohydr. Chem. 1994, 13, 5, p767


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