1, 2, 3, 4, 6-Penta-O-acetyl-D-glucopyranose, CAS:83-87-4

D-Glucopyranose, pentaacetate is a derivative of glucose that belongs to the saccharide family, which is one of the most important class of biomolecules. This compound is also known as PAP and exhibits a unique structure that includes five acetate groups attached to the hydroxyl groups present in different positions of the glucose molecule. It was first synthesized in 1941 by Lemieux and Banting, marking the beginning of the exploration of its diverse applications in chemistry, biology, and material science.

Physical and Chemical Properties

The empirical formula of D-Glucopyranose, pentaacetate is C16H22O11, and its molecular weight is 390.34 g/mol. This compound is a white crystalline powder with a melting point of 112-117?C. It is soluble in organic solvents like ethanol, acetonitrile, and chloroform but insoluble in water due to the presence of the hydrophobic acetyl groups. The compound is stable at room temperature and exhibits a strong odor of acetic acid.

Synthesis and Characterization

The synthesis of D-Glucopyranose, pentaacetate involves the acetylation of glucose using acetic anhydride as a reagent in the presence of a catalyst like sulfuric acid. The reaction mixture is then purified by several techniques such as recrystallization, column chromatography, or distillation. The purity and structure of the compound are confirmed by various analytical methods like infrared (IR) spectroscopy, nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry (MS), and X-ray crystallography.

Analytical Methods

IR spectroscopy is used to confirm the presence of the acetyl groups in the compound as it exhibits characteristic absorption bands at 1750-1700 cm-1. NMR spectroscopy is employed to determine the chemical shifts and multiplicity of protons and carbon atoms in the molecule. MS is used to determine the molecular weight and fragmentation pattern of the compound. X-ray crystallography is used to visualize the crystal structure of the compound in three dimensions.

Biological Properties

D-Glucopyranose, pentaacetate has been reported to exhibit several biological properties such as antibacterial, antifungal, antiparasitic, and antiviral activity. It has been shown to inhibit the growth of various microorganisms like Staphylococcus aureus, Candida albicans, and Plasmodium falciparum. The compound also has the potential to act as an immunomodulator by stimulating the production of cytokines and inducing the differentiation of T cells.

Toxicity and Safety in Scientific Experiments

Several studies have reported that D-Glucopyranose, pentaacetate is non-toxic and safe for use in scientific experiments. However, it is important to handle the compound with caution as it is highly flammable and may cause irritation to the eyes, skin, and respiratory tract. Proper protective measures such as gloves, goggles, and respiratory masks should be used to avoid any possible hazards.

Applications in Scientific Experiments

D-Glucopyranose, pentaacetate has a wide range of applications in scientific experiments. It can be used as a building block for the synthesis of various derivatives that have potential therapeutic applications. The compound can also be used as a protecting agent for hydroxyl groups in other molecules. It has been used as a model compound for studying the conformational behavior of saccharides using NMR spectroscopy. Additionally, the compound has been employed for the preparation of high-performance ceramic materials.

Current State of Research

Recent research has focused on developing new synthetic strategies for the preparation of D-Glucopyranose, pentaacetate derivatives with enhanced biological activity. Studies have also focused on understanding the mechanism of action of the compound and its potential therapeutic applications. The development of new analytical methods for the characterization of the compound has also received significant attention.

Potential Implications in Various Fields of Research and Industry

D-Glucopyranose, pentaacetate has already found numerous applications in various fields of research and industry. In the pharmaceutical industry, it can be used as a starting material for the preparation of glycosylated drugs with improved bioavailability and stability. In the food industry, it can be used as a flavoring agent and a preservative. In material science, it can be used as a building block for the preparation of high-performance materials with unique properties such as hydrophobicity.

Limitations and Future Directions

Despite its numerous applications, D-Glucopyranose, pentaacetate has certain limitations that need to be addressed in future research. One major challenge is to develop more efficient and sustainable synthetic strategies for the preparation of the compound and its derivatives. Future research should also focus on elucidating the precise mechanism of action of the compound and identifying its potential targets in different biological systems. Moreover, the development of new analytical methods for the characterization of the compound and its derivatives will be crucial for advancing research in this field. Finally, studies exploring the biodegradability and environmental impact of the compound will be essential for its safe use in industry.

In conclusion, D-Glucopyranose, pentaacetate is a versatile compound with diverse applications in various fields of research and industry. Its unique structure, physical and chemical properties, and biological activities make it a promising compound for future research and development. However, more research is needed to address its limitations and explore its potential in different fields.