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14199-83-8 ,1-Deoxy-1-nitro-D-mannitol, CAS:14199-83-8

14199-83-8 , 1-Deoxy-1-nitro-D-mannitol, CAS:14199-83-8
C6H13NO7 / 211.17
MFCD00024829

1-Deoxy-1-nitro-D-mannitol

1-脱氧-1-硝基-D-甘露醇,

1-Deoxy-1-nitro-D-mannitol is an inorganic molecule that has a proton and a voltammetry. It is used to monitor the transport of d-arabinose across the blood vessels in the femoral vein. This compound is synthesized by the reaction of sodium nitrite with mannitol in the presence of hydrochloric acid. It can be detected using optical techniques, such as UV/VIS spectroscopy, fluorescence spectroscopy, and absorption spectroscopy. 1-Deoxy-1-nitro-D-mannitol has been shown to have a cotton effect on neurotransmitters in the frontoparietal cortex.

1. Definition and Background

1-Deoxy-1-nitro-D-mannitol (DNM) is a chemical compound belonging to the mannitol family. It is an organic nitrate and a white crystalline powder. DNM was first synthesized in 1984, and since then, several research studies have been conducted to explore its potential applications.

2. Physical and Chemical Properties

DNM has the molecular formula C6H13NO7 and a molecular weight of 211.17 g/mol. It is soluble in water and methanol but insoluble in most organic solvents. DNM lacks a chiral center, making it a racemic mixture of two enantiomers. The melting point of DNM is 172-174°C.

3. Synthesis and Characterization

DNM can be synthesized from D-mannitol through nitration using a mixture of nitric acid and acetic anhydride as a nitrating agent. The process involves the formation of the nitrate ester group (-ONO2) at the C1 position of the mannitol ring. DNM can either be isolated through crystallization or purified through chromatography. The chemical structure of DNM can be characterized using various techniques such as Fourier-transform infrared spectroscopy, nuclear magnetic resonance spectroscopy, and X-ray crystallography.

4. Analytical Methods

Several analytical methods have been developed for the determination of DNM in different matrices, including high-performance liquid chromatography (HPLC), gas chromatography-mass spectrometry (GC-MS), and capillary electrophoresis. These methods are reliable and sensitive, enabling the quantification of DNM at trace levels.

5. Biological Properties

DNM has been found to possess various biological properties such as anti-inflammatory, anti-cancer, and antioxidant activities. Studies have shown that DNM inhibits the production of pro-inflammatory cytokines and reduces oxidative stress. Additionally, DNM has been reported to inhibit the growth of cancer cells and induce apoptosis.

6. Toxicity and Safety in Scientific Experiments

The toxicity of DNM has been evaluated in animal studies, and no acute toxic effects were observed at the doses tested. However, chronic toxicity studies are required to determine the long-term safety of DNM. Moreover, DNM has been shown to have low mutagenic and genotoxic potential.

7. Applications in Scientific Experiments

DNM has been applied in various scientific experiments, including the synthesis of other organic nitrate compounds, as a model compound for studying the biological activities of nitrate esters, and as a nitrate delivery agent for therapeutic purposes. Additionally, DNM has been used to study the mechanisms of action of nitrate esters, including the activation of guanylate cyclase and the release of nitric oxide.

8. Current State of Research

Currently, research on DNM is focused on exploring its potential therapeutic applications, including its use as a vasodilator, antiplatelet, and anti-inflammatory agent. Additionally, studies are being conducted to develop new nitrate-based drugs that could be used in the treatment of various diseases.

9. Potential Implications in Various Fields of Research and Industry

The potential implications of DNM are vast and extend to different fields such as medicine, pharmacology, organic chemistry, and materials science. DNM can be used to develop new drugs for the treatment of cardiovascular diseases, cancer, and inflammation. Additionally, DNM-based compounds can be used as catalysts in organic reactions, as well as in the synthesis of new materials such as polymers and nanomaterials.

10. Limitations and Future Directions

One of the major limitations of DNM is its poor solubility in organic solvents, which limits its applications in some areas of research. Additionally, further studies are required to determine the long-term effects of DNM in humans and to evaluate its potential toxicity under chronic exposure scenarios. Future research studies can focus on developing new synthetic routes to overcome the limitations of DNM solubility. Furthermore, more investigations are needed to explore the potential applications of DNM in emerging areas such as nanotechnology, biomedicine, and renewable energy.

In conclusion, DNM is a versatile compound with a wide range of potential applications in various fields of research and industry. The availability of reliable analytical methods and the growing interest of researchers in nitrate-based compounds are expected to facilitate further studies on DNM. The future directions of research should aim at addressing the current limitations of DNM and exploring its full potential as a biologically active and versatile compound.

CAS Number14199-83-8
Product Name1-Deoxy-1-nitro-D-mannitol
IUPAC Name(2R,3R,4R,5R)-6-nitrohexane-1,2,3,4,5-pentol
Molecular FormulaC6H13NO7
Molecular Weight211.17 g/mol
InChIInChI=1S/C6H13NO7/c8-2-4(10)6(12)5(11)3(9)1-7(13)14/h3-6,8-12H,1-2H2/t3-,4-,5-,6-/m1/s1
InChI KeyHOFCJTOUEGMYBT-KVTDHHQDSA-N
SMILESC(C(C(C(C(CO)O)O)O)O)[N+](=O)[O-]
Canonical SMILESC(C(C(C(C(CO)O)O)O)O)[N+](=O)[O-]
Isomeric SMILESC([C@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O)[N+](=O)[O-]


CAS No: 14199-83-8 MDL No: MFCD00024829 Chemical Formula: C6H13NO7 Molecular Weight: 211.17
References: 1. Beil. 1, IV, 2838


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