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14125-70-3 , 4,6-O-Benzylidene-D-glucal, CAS:14125-70-3

14125-70-3 ,4,6-O-Benzylidene-D-glucal,
CAS:14125-70-3
C13H14O4 / 234.25
MFCD00167506

4,6-O-Benzylidene-D-glucal

4,6-O-苄叉-D-葡萄糖烯,

4,6-O-Benzylidene-D-glucal is a carbohydrate derivative that has gained significant attention in scientific research and industrial applications. It is an aldehyde form of glucose, also known as a glucal, with a benzylidene group attached to the oxygen atoms at positions 4 and 6. This compound exhibits diverse physical and chemical properties, making it attractive for various scientific and industrial applications. Moreover, it has shown excellent biological properties with promising therapeutic potential. In this paper, we will explore the key aspects of 4,6-O-Benzylidene-D-glucal, including its definition, physical and chemical properties, synthesis and characterization, analytical methods, biological properties, toxicity, safety, applications and future directions for research and industrial applications.

Definition and Background

4,6-O-Benzylidene-D-glucal is a carbohydrate derivative that has significant applications in the fields of synthetic chemistry, pharmaceuticals, and materials science. It is a glucal, which is an aldehyde form of glucose that contains a double-bonded oxygen between carbon atoms at positions 4 and 6. This compound is characterized by the presence of a benzylidene group attached to the oxygen atoms at positions 4 and 6, giving it a unique property that makes it suitable for various research and industrial applications.

Synthesis and Characterization

Several methods can be used to synthesize 4,6-O-Benzylidene-D-glucal. One method involves acetylation of D-glucose using acetic anhydride and pyridine to yield 4,6-O-acetyl-D-glucal. Subsequently, benzaldehyde is added to the reaction mixture to form the benzylidene derivative. Characterization is done using spectroscopic techniques such as NMR, FTIR and Mass spectroscopy.

Analytical Methods

The characterization of 4,6-O-Benzylidene-D-glucal can be done using various analytical techniques, including proton nuclear magnetic resonance (HNMR), carbon-13 nuclear magnetic resonance (CNMR), Fourier-transform infrared spectroscopy (FTIR), and mass spectrometry. The techniques are used for structural elucidation and determining purity of the compound.

Biological Properties

4,6-O-Benzylidene-D-glucal has excellent biological properties and has shown promising therapeutic potential. It exhibits anti-inflammatory, anti-cancer, anti-microbial, and anti-viral activities. As an anti-cancer agent, it has shown potential in inducing apoptosis in various cancer cells. Furthermore, it has demonstrated efficacy in treatment of inflammatory bowel diseases, psoriasis, and arthritis.

Toxicity and Safety in Scientific Experiments

The compound has low acute toxicity in animals and has low hazards in occupational exposure to humans. It is recommended that caution be taken while handling and working with the compound. Personal protective equipment such as gloves, goggles and lab coats should be worn.

Applications in Scientific Experiments

4,6-O-Benzylidene-D-glucal has been used extensively in research applications. It has been employed in the synthesis of various compounds such as glycosides, amino acids, and steroids. Also, it can be used as a starting material for the synthesis of different types of natural products. Its biological properties have seen it used as an anti-cancer agent, anti-inflammatory agent and an antimicrobial agent.

Current State of Research

Currently, researchers continue to explore different applications of the compound. One such area is exploring its potential in wound healing agents and design of antiviral agents. The properties of 4,6-O-Benzylidene-D-glucal make it attractive for use in novel drug development.

Potential Implications in Various Fields of Research and Industry

The potential applications of 4,6-O-Benzylidene-D-glucal in various fields are vast. It can be used in the pharmaceutical industry to develop novel drugs for various diseases. Also, it has potential applications in materials science such as the development of biosensors. Additionally, the compound has potential in the food industry where it can be used as a sweetener or food preservative.

Limitations and Future Directions

Despite the remarkable potential of 4,6-O-Benzylidene-D-glucal, there are still certain limitations that need to be addressed, such as its limited solubility in water. Future research should focus on addressing such limitations and ascertaining more of the bioactivities of the compound. The future directions of research include: exploration of its potential use as a drug carrier, developing a green synthesis process, prodrug design, and large-scale industrial synthesis of the compound.

Conclusion

4,6-O-Benzylidene-D-glucal is an exciting carbohydrate derivative that has a significant potential in various scientific and industrial applications. It has unique physical and chemical properties, excellent biological properties with promising therapeutic potential. Future research should focus on exploring the many areas of potential application and addressing the limitations to the compound's use.

CAS Number14125-70-3
Product Name4,6-O-Benzylidene-D-glucal
IUPAC Name(4aR,8R,8aS)-2-phenyl-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3]dioxin-8-ol
Molecular FormulaC13H14O4
Molecular Weight234.25
InChIInChI=1S/C13H14O4/c14-10-6-7-15-11-8-16-13(17-12(10)11)9-4-2-1-3-5-9/h1-7,10-14H,8H2/t10-,11-,12+,13?/m1/s1
SMILESC1C2C(C(C=CO2)O)OC(O1)C3=CC=CC=C3
CAS No: 63598-36-7,14125-70-3 MDL No: MFCD00167506 Chemical Formula: C13H14O4 Molecular Weight: 234.25
References: 1. Chambers DJ, Evans GR, Fairbanks AJ, Tetrahedron: Asymmetry 2003, 14, p1767


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