10343-06-3 , 2,3,4,6-O-Tetraacetyl-D-glucose; Tetraacetyl-D-glucose,
2,3,4,6-O-四乙酰-D-葡萄糖,
CAS:10343-06-3
C14H20O10 / 348.303
MFCD00061634
2,3,4,6-O-四乙酰-D-葡萄糖,
2,3,4,6-Tetra-O-acetyl-D-glucopyranose, also known as Ac-D-glucose, is a derivative of glucose that is commonly used in scientific research and industry. It is a white crystalline powder that is soluble in some organic solvents. This paper aims to provide a comprehensive overview of Ac-D-glucose, including its definition, physical and chemical properties, synthesis and characterization, analytical methods, biological properties, toxicity and safety in scientific experiments, current state of research, potential implications in various fields of research and industry, limitations, and future directions.
Definition and Background:
2,3,4,6-Tetra-O-acetyl-D-glucopyranose is a derivative of glucose that is commonly used in organic chemistry and biochemistry. It is composed of a six-membered ring made up of carbon, hydrogen, and oxygen atoms, with an acetyl group attached to each of the four hydroxyl groups on the ring.
Synthesis and Characterization:
2,3,4,6-Tetra-O-acetyl-D-glucopyranose can be synthesized from glucose through a process called acetylation. This involves the addition of acetic anhydride and a catalyst, such as pyridine, to glucose in a solvent, such as acetone. The resulting 2,3,4,6-Tetra-O-acetyl-D-glucopyranose can then be purified through recrystallization.
Characterization of 2,3,4,6-Tetra-O-acetyl-D-glucopyranose is typically done through various analytical techniques, including nuclear magnetic resonance (NMR) spectroscopy, Fourier transform infrared spectroscopy (FTIR), and high-performance liquid chromatography (HPLC).
Analytical Methods:
2,3,4,6-Tetra-O-acetyl-D-glucopyranose can be analyzed through various methods, including HPLC, NMR spectroscopy, mass spectrometry, and FTIR spectroscopy. These methods can be used to determine the purity and identity of 2,3,4,6-Tetra-O-acetyl-D-glucopyranose, as well as its structure and composition.
Biological Properties:
2,3,4,6-Tetra-O-acetyl-D-glucopyranose has been shown to have a variety of biological properties, including its ability to inhibit the activity of certain enzymes, such as beta-glucosidase and alpha-amylase, which are involved in the breakdown of carbohydrates. It has also been shown to have anti-inflammatory and antioxidant properties.
Toxicity and Safety in Scientific Experiments:
2,3,4,6-Tetra-O-acetyl-D-glucopyranose is generally considered to be safe for use in scientific experiments, with no known significant toxicity or safety concerns. However, like any chemical, it should be handled with care, and appropriate safety precautions should be taken when handling and disposing of it.
Applications in Scientific Experiments:
2,3,4,6-Tetra-O-acetyl-D-glucopyranose is commonly used in scientific research and industry, particularly in the fields of organic chemistry and biochemistry. It is used as a reagent in the synthesis of other compounds, and as a substrate for enzymes involved in carbohydrate metabolism.
Current State of Research:
Research on 2,3,4,6-Tetra-O-acetyl-D-glucopyranose is ongoing, with new applications and potential uses being investigated. Recent studies have focused on its role in the inhibition of certain enzymes, as well as its potential use in the treatment of various medical conditions.
Potential Implications in Various Fields of Research and Industry:
2,3,4,6-Tetra-O-acetyl-D-glucopyranose has the potential to be used in a variety of applications in various fields of research and industry. It can be used as a substrate for enzymes involved in carbohydrate metabolism, as a reagent in organic synthesis, and as a potential therapeutic agent.
Limitations and Future Directions:
While 2,3,4,6-Tetra-O-acetyl-D-glucopyranose has many potential uses and applications, there are also limitations to its use. One limitation is its relatively low solubility, which may limit its usefulness in certain applications. Future research may focus on developing new derivatives of 2,3,4,6-Tetra-O-acetyl-D-glucopyranose with improved properties and solubility, as well as investigating its potential use in the development of new therapies for various medical conditions.
Future Directions:
1. Investigation of the potential use of 2,3,4,6-Tetra-O-acetyl-D-glucopyranose in the development of new therapies for diseases involving carbohydrate metabolism.
2. Development of new derivatives of 2,3,4,6-Tetra-O-acetyl-D-glucopyranose with improved properties, including solubility and biological activity.
3. Investigation of the effects of 2,3,4,6-Tetra-O-acetyl-D-glucopyranose on the human microbiome.
4. Investigation of the potential use of 2,3,4,6-Tetra-O-acetyl-D-glucopyranose in agriculture and food production.
5. Investigation of the potential use of 2,3,4,6-Tetra-O-acetyl-D-glucopyranose in the development of new synthetic materials.
6. Investigation of the potential use of 2,3,4,6-Tetra-O-acetyl-D-glucopyranose in the development of new renewable energy sources.
7. Investigation of the interactions between 2,3,4,6-Tetra-O-acetyl-D-glucopyranose and other compounds, including enzymes and proteins.
8. Investigation of the potential use of 2,3,4,6-Tetra-O-acetyl-D-glucopyranose in the treatment of cancer.
9. Investigation of the potential use of 2,3,4,6-Tetra-O-acetyl-D-glucopyranose in the development of new drugs for neurological disorders.
10. Investigation of the effects of 2,3,4,6-Tetra-O-acetyl-D-glucopyranose on the environment, including its biodegradability and potential impact on ecosystems.
CAS Number | 10343-06-3 |
Product Name | 2,3,4,6-Tetra-O-acetyl-D-glucopyranose |
IUPAC Name | [(2R,3R,4S,5R)-3,4,5-triacetyloxy-6-hydroxyoxan-2-yl]methyl acetate |
Molecular Formula | C₁₄H₂₀O₁₀ |
Molecular Weight | 348.303 |
InChI | InChI=1S/C14H20O10/c1-6(15)20-5-10-11(21-7(2)16)12(22-8(3)17)13(14(19)24-10)23-9(4)18/h10-14,19H,5H2,1-4H3/t10-,11-,12+,13-,14?/m1/s1 |
SMILES | CC(=O)OCC1C(C(C(C(O1)O)OC(=O)C)OC(=O)C)OC(=O)C |
Synonyms | 2,3,4,6-Tetraacetate D-Glucopyranose; |
CAS No: 3947-62-4,10343-06-3 Synonyms: 2,3,4,6-Tetraacetate D-glucopyranose MDL No: MFCD00061634 Chemical Formula: C14H20O10 Molecular Weight: 348.303 |
References: 1. Sambaiaha T, Fanwick PE, Cushman M, Synthesis 2001, p1450-14522. Sofian A, Lee C, J. Carbohydr. Chem. 2001, Vol20, Pt6, p431-440 |
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