18423-66-0,D-Xylonic acid-1,4-lactone,
D-木糖酸-1,4-内酯,
CAS:18423-66-0
C5H8O5 / 148.11
MFCD00076092
D-木糖酸-1,4-内酯
D-Xylono-1,4-lactone, also known as D-xylonolactone, is a six-membered cyclic sugar molecule with a lactone ring. It is classified as a chemical compound that belongs to the class of monosaccharides and is a derivative of Xylose, a simple sugar. The molecule is produced by the oxidation of D-Xylose sugar or its derived compounds. The stereochemistry of the molecule determines its biological activity and properties.
Physical and Chemical Properties:
D-Xylono-1,4-lactone is an odorless, white crystalline solid that is soluble in water and polar solvents but insoluble in organic solvents. The molecule has a melting point of 182-187°C, and its boiling point is 462°C. It is a stable compound, with a low reactivity towards acids, bases, and oxidizing agents.
Synthesis and Characterization:
D-Xylono-1,4-lactone can be synthesized through the oxidation of xylitol, which can be obtained from renewable biomass sources such as corn cobs, sugarcane bagasse, and coconut shells. The process involves the use of air as an oxidizing agent and a catalyst such as copper(II) sulfate or cerium(IV) ammonium nitrate. The purity of the produced D-xylonolactone can be determined using various techniques such as high-performance liquid chromatography (HPLC), gas chromatography (GC), and nuclear magnetic resonance (NMR) spectroscopy.
Analytical Methods:
Methods used for the analysis of D-xylonolactone include gas chromatography-mass spectrometry (GC-MS), high-performance liquid chromatography (HPLC), Fourier transform infrared spectroscopy (FTIR), NMR spectroscopy, and UV spectrophotometry.
Biological Properties:
D-Xylono-1,4-lactone has been found to exhibit several biological activities, including antibacterial, anticancer, and anti-inflammatory properties. Research studies have shown that D-xylonolactone is effective at inhibiting bacterial growth, particularly against Escherichia coli. The compound also possesses potential anticancer activity against certain cancer cell lines such as HepG2 and MCF-7 through induction of apoptosis and cell cycle arrest. In addition, D-xylonolactone has anti-inflammatory properties, reducing inflammation in vitro and in vivo.
Toxicity and Safety in Scientific Experiments:
The toxicity of D-xylonolactone has been studied, and it is considered to be safe for use in scientific experiments. The compound has low toxicity and no adverse effects on normal cell growth in vitro. The effective dose of D-xylonolactone varies depending on the application, and thus, appropriate dosages should be determined for its safe use.
Applications in Scientific Experiments:
D-Xylono-1,4-lactone has various applications in scientific experiments, including its use as an intermediate for the synthesis of several biologically active compounds such as flavonoids, lignans, and phenolics. It is also used as a potential food additive, as well as a precursor for the synthesis of xylitol, which is used as a low-calorie sweetener.
Current State of Research:
The current research on D-xylonolactone focuses on exploring its various biological activities and uncovering its potential applications in various fields. Research studies have been conducted to investigate its role in treating diseases such as cancer and inflammation. Moreover, the synthesis of D-xylonolactone from renewable biomass sources has gained much attention due to its potential use as a sustainable chemical and fuel source.
Potential Implications in Various Fields of Research and Industry:
D-Xylono-1,4-lactone has the potential to play a significant role in various fields of research and industry. In the pharmaceutical industry, it can be used as a precursor for the synthesis of novel drugs with diverse biological activities. In the food industry, it can be used as an alternative sweetener due to its low-caloric content. Moreover, it can be utilized as a building block for the synthesis of various bio-based materials and chemicals.
Limitations and Future Directions:
Despite its several potential applications, D-xylonolactone has some limitations, such as its low solubility in organic solvents, which makes it challenging to use in industrial processes. Future directions for research could include exploring novel methods for synthesizing D-xylonolactone using non-toxic and sustainable catalysts. Further studies could also be conducted to investigate its potential applications in fields such as biotechnology, material science, and renewable energy. Finally, more in-depth research into the mechanisms underlying its biological activities will assist in revealing its potential to serve as a therapeutic agent for various diseases.
CAS Number | 18423-66-0 |
Product Name | D-Xylono-1,4-lactone |
IUPAC Name | (3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-one |
Molecular Formula | C5H8O5 |
Molecular Weight | 148.11 g/mol |
InChI | InChI=1S/C5H8O5/c6-1-2-3(7)4(8)5(9)10-2/h2-4,6-8H,1H2/t2-,3+,4-/m1/s1 |
InChI Key | CUOKHACJLGPRHD-FLRLBIABSA-N |
SMILES | C(C1C(C(C(=O)O1)O)O)O |
Canonical SMILES | C(C1C(C(C(=O)O1)O)O)O |
Isomeric SMILES | C([C@@H]1[C@@H]([C@H](C(=O)O1)O)O)O |
CAS No: 15384-37-9,18423-66-0 Synonyms: D-Xylono-1,4-lactoneD-Xylonic acid gamma-lactone MDL No: MFCD00076092 Chemical Formula: C5H8O5 Molecular Weight: 148.11 |
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