Diacetone-D-mannitol CAS 1707-77-3 Structural formula: C12H22O6 is a white crystalline powder, melting point is 120-122°C (lit.), specific optical rotation is 6º (c=5,Chloroform), boiling point is 382.0±32.0°C (Predicted), density is 1.175±0.06g/cm3(Predicted), solubility (methanol 100mg/mL), acidity coefficient (pKa) is 12.98±0.20 (Predicted). It is a representative compound of polyhydroxy compounds, which is a new class of chiral selective agent with simple preparation and low price, and it can be used to separate a variety of chiral drugs in NACE with good separation effect. It is used as an intermediate in the pharmaceutical field due to its unique chemical structure.
As a novel chiral selective agent, bisacetone-D-mannitol plays an important role in chiral separation and recognition. Its chiral center can form stable complexes with the substances to be separated, thus realizing efficient chiral separation. With the continuous development of science and technology, its application fields will be more extensive.
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C.F |
C12H22O6 |
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E.M |
262 |
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M.W |
262 |
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m/z |
262 (100.0%), 263 (13.0%), 264 (1.2%) |
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E.A |
C, 54.95; H, 8.45; O, 36.60 |
Diacetone-D-mannitol (also known as D-mannitol diketone) is synthesized in a variety of ways, and the following are some of the major synthesis methods and their characteristics:
Synthesis catalyzed by molten zinc chloride:
The unsaturated ester 20 d-mannitol is added to a stirred solution of dry acetone with molten zinc chloride.
Stirring was continued until d-mannitol was completely dissolved (about 22 hours).
The reaction mixture was poured into a stirred and cooled aqueous solution of potassium carbonate.
The precipitate was removed by filtration and washed thoroughly with dichloromethane (DCM).
The aqueous filtrate was evaporated to remove acetone and extracted by DCM.
The organic washings and extracts were washed with cold water, dried with magnesium sulfate, evaporated to a solid residue, and recrystallized to give bisacetone-D-mannitol.
Synthesized using pyridine salt catalyst:
The reaction of D-mannitol and 2,2-dimethoxypropane in dioxane solvent was carried out in the presence of pyridine salt catalyst.
This synthetic route has the advantage of high selectivity for the product, can effectively avoid and reduce the generation of by-products, improves the conversion rate of raw materials, and has the effect of high product yield and purity.
Other synthetic methods:
Methods using a mixed solvent of acetone or acetone lower alcohols, a magnesium sulfate absorbent, and potassium bisulfate as a catalyst are also included.
There are also methods using p-toluenesulfonic acid or stannous chloride as a catalyst in DMSO or DMF solvents, but these methods suffer from the problem of strong acidity, which tends to transform the product to monoacetonide by-products and reduce the quality of the product.
Diacetone-D-mannitol is a white crystalline powder substance with specific physical and chemical properties. Its melting point is 120-122 ° C, specific optical rotation is 6 º (c=5, Chloroform), boiling point is 382.0 ± 32.0 ° C, density is 1.175 ± 0.06g/cm3, and refractive index is 6.5 ° (C=8, CHCl3). In addition, diacetone-D-mannitol has a high solubility in methanol, with an acidity coefficient (pKa) of 12.98 ± 0.20. These properties provide the foundation for its application in the field of medicine.
Application in the field of medicine
1. Separation and analysis of chiral drugs
As a representative compound of polyhydroxy compounds, an important application in the pharmaceutical field is as a chiral selector. The efficacy and metabolism of chiral drugs in living organisms are often closely related to their three-dimensional structure, so the separation and analysis of chiral drugs are important links in drug development and production processes. Due to the fact that its two enantiomers often exhibit different pharmacological, pharmacokinetic, and toxicological properties, it can be used in non-aqueous capillary electrophoresis (NACE) to separate multiple chiral drugs with good separation efficiency. This characteristic makes it have broad application prospects in the field of chiral drug separation and analysis.
2. Pharmaceutical excipients and additives
Although its main applications in the pharmaceutical field are as chiral selectors and drug synthesis intermediates, its potential as pharmaceutical excipients and additives cannot be ignored. Due to its unique physical and chemical properties, it can be used as a stabilizer, thickener, dispersant, etc. for drugs, improving their stability and bioavailability. In addition, because of its sweet taste, it can also be used as a sweetener for sugar free or low sugar drugs to meet the drug needs of special populations (such as diabetes patients).
3. Development of new drugs
With the deepening of research on it, people have found that it also has great potential in the development of new drugs. For example, Petrosiols A-E can participate in the synthesis of compounds with the potential to treat Alzheimer's disease and Parkinson's syndrome. In addition, it can also be used to synthesize (-) Orthodiffenes A-C compounds with good anti-tumor activity, which exhibit significant inhibitory activity against cancer cells such as HL-60 and Jurkat. These studies indicate broad application prospects in the field of new drug development.
Specific application cases in the field of medicine
1. diabetes drugs
Diabetes is a chronic metabolic disease, and its treatment requires long-term medication. As an intermediate in drug synthesis, it can participate in the synthesis of compounds with hypoglycemic effects. For example, by inhibiting the decomposition of liver glycogen in the liver and promoting the utilization of glucose in peripheral tissues, the substance itself or its derivatives can reduce the level of glucose in the body, thus improving the blood sugar status of diabetes patients. In addition, because of its low calorie, not easy to cause blood sugar fluctuations and other characteristics, it can also be used as an auxiliary food ingredient for diabetes patients to meet their sweet needs while avoiding blood sugar fluctuations.
3. Antiviral drugs
Viral diseases such as AIDS and influenza pose a great threat to human health. Can participate in the synthesis of compounds with antiviral activity. For example, sulfur-containing fused tetracyclic nitrogen-containing sugar derivatives are synthesized from them or their derivatives, which have strong inhibitory effects on HIV virus. Through further research and optimization, these compounds are expected to become a new generation of antiviral drugs, providing more options for the treatment of viral diseases.
4. Medications for the treatment of neurological disorders
Neurological diseases such as Alzheimer's disease and Parkinson's syndrome seriously affect the quality of life of patients. Can participate in the synthesis of compounds with the potential to treat neurological diseases. For example, Petrosiols A-E is synthesized from it or its derivatives, and these compounds have certain therapeutic effects on neurological diseases such as Alzheimer's disease and Parkinson's syndrome. Through further research and optimization, these compounds are expected to become a new generation of therapeutic drugs for neurological diseases, bringing better therapeutic effects to patients.
Chiral polyhydroxy compounds are polyhydroxy compounds that contain two or more hydroxyl groups in their molecular structure (such as D/L-tartaric acid, series D/L-tartrate esters, D-gluconic acid, D/L-sorbose, D-mannitol, lactose acid, etc.). Diacetone-D-mannitol is a representative compound of this type of polyhydroxy compound, which is a novel chiral selector with simple preparation and low cost. It can be used in NACE to separate various chiral drugs with good separation effects, but its application research in actual sample separation and analysis is still limited.
Mainly due to the fact that the two enantiomers of diacetone-D-mannitol often exhibit different pharmacological, pharmacokinetic, and toxicological properties, generally speaking, the (R) - enantiomer plays a major role in clinical practice, while the (S) - enantiomer is ineffective, has low activity, or even toxic.
Therefore, in order to improve the efficacy of chiral drugs such as diacetone-D-mannitol, reduce toxic side effects, establish a simple and efficient method for separating and detecting chiral drugs, and conduct single enantiomer research to understand their physiological activity and pharmacological effects, it is of great significance to achieve safe, rational, and effective drugs. In order to achieve safe and rational use of chiral drugs, ensure stable and uniform drug quality, and meet medication requirements, it is necessary to carry out drug quality control, and the determination of enantiomer content is one of the important control indicators.
Diacetone-D-mannitol is an important organic compound with wide application value in the pharmaceutical, food, and chemical industries. As a derivative of D-mannitol, its unique chemical structure endows it with special properties and functions. The discovery of D-mannitol can be traced back to plant chemistry research in the early 19th century.
In 1806, French chemist Louis Nicolas Vauquelin first isolated this sweet substance from honeydew (manna, a exudate from the Fraxinus ornus). This natural product was named "mannite" due to its origin, and later renamed "mannitol" (mannitol). German chemist Joseph Louis Gay Lussac further studied this substance in 1811 and determined its fundamental properties.
Subsequently, in 1826, another French chemist Henri Braconnot successfully isolated mannitol from mushrooms, algae, and other plants, confirming its widespread presence in nature. With the development of organic chemical structure theory, scientists began to explore the molecular structure of mannitol in the second half of the 19th century.
German chemist Justus von Liebig first synthesized acetone in 1832 and studied its properties. With the development of organic chemistry, acetone is not only used as a solvent, but also gradually becomes an important reactant and synthetic intermediate.
In 1870, German chemist Emil Fischer began systematically studying the structure of carbohydrate substances, which ultimately earned him the Nobel Prize in Chemistry in 1902. Fischer determined through a series of clever chemical reactions that mannitol is a six carbon sugar alcohol with the molecular formula C ₆ H ₁₄ O ₆, and elucidated its stereochemical structure.
At the beginning of the 20th century, with the advancement of organic synthetic chemistry, chemists developed various methods for synthesizing mannitol. The most important one is the process of preparing mannitol from D-glucose or D-fructose through hydrogenation reduction. These synthetic methods laid the foundation for the subsequent research on mannitol derivatives.
Acetone, as a simple and important organic solvent and reagent, was widely studied and applied in the mid-19th century.
Diacetone-D-mannitol is a versatile compound with significant potential in pharmaceuticals, chromatography, and organic synthesis. Its unique physicochemical properties, coupled with ongoing research in green chemistry and nanotechnology, position it as a critical material for future industrial applications. As demand for chiral compounds and sustainable processes rises, DADM is poised to play a pivotal role in advancing chemical manufacturing and drug development.
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