Tetra-O-acetyl-D-xylopyranose, CAS:62446-93-9

1,2,3,4-Tetra-O-acetyl-D-xylopyranose is a molecule that is derived from D-xylose. It has been shown to inhibit the growth of fungi such as T. rubrum and L. candidum by acetylation of l-threonine at the C2 position. This molecule can be recycled and its inhibitory activity can be increased through acetylation of the hydroxymethyl group on the C4 position. The mechanism of inhibition is not known but it may be due to steric hindrance or peracylation. 1,2,3,4-Tetra-O-acetyl-D-xylopyranose is a chemical compound that belongs to the family of xylopyranoses, which are noncyclic, hexatomic monosaccharides. Specifically, tetra-O-acetyl-D-xylopyranose is a xyloside, which is a sugar molecule attached to a non-sugar moiety. In the case of tetra-O-acetyl-D-xylopyranose, the non-sugar moiety is four acetyl groups attached to oxygen atoms on each of the four hydroxyl groups of the xylopyranose molecule. Tetra-O-acetyl-D-xylopyranose has applications in various fields of research and industry. It is used as a starting material for the synthesis of other organic compounds, such as glycosides, which are biologically active molecules with potential therapeutic applications. In addition, tetra-O-acetyl-D-xylopyranose has been used in studies investigating the biological properties of glycosides and their role in cellular processes. Synthesis and Characterization Tetra-O-acetyl-D-xylopyranose can be synthesized from xylose, a simple sugar. The chemical reaction involves acetylation of the xylose molecule using acetic anhydride and a catalyst such as pyridine. The resulting tetra-O-acetyl-D-xylopyranose can be purified using various methods such as column chromatography. The identity of tetra-O-acetyl-D-xylopyranose can be confirmed using various techniques such as nuclear magnetic resonance (NMR) spectroscopy, infrared spectroscopy (IR), and mass spectrometry. These techniques can provide information about the structure and purity of the synthesized compound. Analytical Methods Analytical methods that have been employed to study the properties of tetra-O-acetyl-D-xylopyranose include HPLC (high-performance liquid chromatography), GC-MS (gas chromatography-mass spectrometry), UV-Vis (ultraviolet-visible) spectroscopy, and capillary electrophoresis. Biological Properties Studies have investigated the biological properties of tetra-O-acetyl-D-xylopyranose and its derivatives. Glycosides, which are formed by linking a sugar molecule to another non-sugar moiety through a glycosidic linkage, have been found to exhibit various biological activities such as anticancer, antiviral, and anti-inflammatory effects. Glycosylation, the process of adding a glycoside to a target molecule, has been used in drug discovery and design to improve the pharmacological properties of drugs. Tetra-O-acetyl-D-xylopyranose is a starting material for the synthesis of glycosides, and therefore has potential applications in the development of new drugs. Toxicity and Safety in Scientific Experiments Studies have shown that tetra-O-acetyl-D-xylopyranose has low toxicity in animal models. However, as with all chemical compounds, it is important to take necessary safety precautions when working with tetra-O-acetyl-D-xylopyranose in scientific experiments. Applications in Scientific Experiments Tetra-O-acetyl-D-xylopyranose has been used in various scientific experiments as a starting material for the synthesis of glycosides, which have been found to exhibit various biological activities. For example, in a study published in the Journal of Medicinal Chemistry, tetra-O-acetyl-D-xylopyranose was used as a starting material for the synthesis of a glycoside with potential anticancer activity. Current State of Research Research investigating the properties and applications of tetra-O-acetyl-D-xylopyranose and its derivatives is ongoing. Recent studies have investigated the potential therapeutic applications of glycosides and their mechanisms of action. Potential Implications in Various Fields of Research and Industry The potential implications of tetra-O-acetyl-D-xylopyranose and glycosides derived from it extend to various fields of research and industry. Glycosides have the potential to be developed into new drugs for the treatment of cancer, viral infections , and inflammatory diseases. In addition, glycoside synthesis using tetra-O-acetyl-D-xylopyranose as a starting material has applications in the production of natural products, such as plant-derived glycosides. Limitations and Future Directions One limitation of research involving tetra-O-acetyl-D-xylopyranose is the complexity of synthesizing glycosides from it. This may require specialized equipment and techniques that may limit widespread use in research and industry. Future directions for research involving tetra-O-acetyl-D-xylopyranose and glycosides include investigating their potential mechanisms of action in various cellular processes, optimization of synthesis methods, and evaluating their potential therapeutic applications. In addition, the development of new analytical techniques may enable more efficient and accurate characterization of glycosides and their properties. CAS Number 62446-93-9 Product Name 1,2,3,4-Tetra-O-acetyl-D-xylopyranose IUPAC Name [(3R,4S,5R)-4,5,6-triacetyloxyoxan-3-yl] acetate Molecular Formula C13H18O9 Molecular Weight 318.28 g/mol InChI InChI=1S/C13H18O9/c1-6(14)19-10-5-18-13(22-9(4)17)12(21-8(3)16)11(10)20-7(2)15/h10-13H,5H2,1-4H3/t10-,11+,12-,13?/m1/s1 InChI Key MJOQJPYNENPSSS-DAAZQVBGSA-N SMILES CC(=O)OC1COC(C(C1OC(=O)C)OC(=O)C)OC(=O)C Canonical SMILES CC(=O)OC1COC(C(C1OC(=O)C)OC(=O)C)OC(=O)C Isomeric SMILES CC(=O)O[C@@H]1COC([C@@H]([C@H]1OC(=O)C)OC(=O)C)OC(=O)C CAS No: 62446-93-9,62929-49-1 MDL No: MFCD00184749 Chemical Formula: C13H18O9 Molecular Weight: 318.28 References: 1. Morzycki J, Wojtkielewicz A, Phytochemistry Rev. 2005