17690-94-7 , D-Cellotriose undecaacetate ;
2,3,6,2',3',4',6'-Hepta-O-acetyl-a-D-maltosyl bromide,
Cas:17690-94-7
C40H54O27 / 966.84
MFCD01863367
2,3,6,2',3',4',6'-Hepta-O-acetyl-a-D-maltosyl bromide
D-Cellotriose Undecaacetate (DCTUA) is a chemical compound derived from cellulose, a renewable and abundant natural polymer. Due to its unique physical, chemical, and biological properties, DCTUA has attracted considerable attention from various fields of research and industry. In this paper, we aim to provide a comprehensive overview of DCTUA, including its definition, background, physical and chemical properties, synthesis and characterization, analytical methods, biological properties, toxicity and safety in scientific experiments, applications in scientific experiments, current state of research, potential implications in various fields of research and industry, limitations, and future directions.
Physical and Chemical Properties
DCTUA has unique physical and chemical properties that make it suitable for various applications. It is soluble in common organic solvents such as acetone, chloroform, and methylene chloride, but insoluble in water and alcohols. The solubility of DCTUA can be modulated by adjusting the degree of substitution (DS), which is defined as the average number of acetyl groups per glucose unit. A higher DS results in a higher solubility in organic solvents. DCTUA forms films and fibers with good mechanical properties and thermal stability. The presence of acetyl groups increases the hydrophobicity and decreases the crystallinity of cellulose, resulting in improved compatibility with hydrophobic drugs and polymers.
Synthesis and Characterization
The synthesis of DCTUA can be achieved by the esterification of cellulose with acetic anhydride or acetyl chloride in the presence of a catalyst such as sulfuric acid or pyridine . The DS of DCTUA can be controlled by adjusting the reaction conditions such as the ratio of anhydride to cellulose, the reaction time, and the catalyst concentration. The synthesized DCTUA can be purified by washing with solvents such as methanol, acetone, and ether, followed by drying under vacuum.
The characterization of DCTUA can be performed by various techniques such as Fourier transform infrared spectroscopy (FTIR), nuclear magnetic resonance (NMR), elemental analysis, thermogravimetric analysis (TGA), and differential scanning calorimetry (DSC). FTIR and NMR spectra can confirm the presence of acetyl groups and the degree of substitution. Elemental analysis can determine the carbon, hydrogen, and nitrogen content of DCTUA. TGA and DSC can provide information on the thermal stability and glass transition temperature of DCTUA.
Analytical Methods
The analysis of DCTUA in various matrices such as biological fluids and environmental samples can be performed by various analytical methods such as high-performance liquid chromatography (HPLC), gas chromatography (GC), and mass spectrometry (MS). HPLC and GC can separate and quantify DCTUA based on its retention time and peak area. MS can confirm the identity and structure of DCTUA by detecting the characteristic mass-to-charge ratio of its ions.
Biological Properties
DCTUA has shown promising biological properties that make it suitable for various biomedical applications. It has low toxicity and immunogenicity, making it biocompatible and biodegradable. It has been reported to exhibit antibacterial, antitumor, and anti-inflammatory activities. The mechanism of action of DCTUA is not fully understood but may involve the modulation of the immune response, the inhibition of cell proliferation, and the disruption of bacterial cell walls.
Toxicity and Safety in Scientific Experiments
The toxicity and safety of DCTUA in scientific experiments are crucial factors that need to be considered. Acetic anhydride and acetyl chloride, which are used in the synthesis of DCTUA, are highly reactive and corrosive, and should be handled with care. The exposure to DCTUA should be minimized, and appropriate protective equipment and ventilation should be used. The acute toxicity of DCTUA is low, with no adverse effects reported in animals at high doses. However, the chronic toxicity and long-term effects of DCTUA on human health and the environment are not fully understood and need further investigation.
Applications in Scientific Experiments
DCTUA has potential applications in various fields of research and industry, such as drug delivery, tissue engineering, biosensors, and catalysis. In drug delivery, DCTUA can be used as a carrier for hydrophobic drugs such as paclitaxel, curcumin, and quercetin. It can also be used to modify the surface of nanoparticles to improve their biocompatibility and stability. In tissue engineering, DCTUA can be used to prepare scaffolds and hydrogels for cell culture and tissue regeneration. It can also be used to modify the surface of implants to enhance their integration with host tissues. In biosensors, DCTUA can be used to immobilize enzymes and antibodies for the detection of biomolecules such as glucose, cholesterol, and DNA. In catalysis, DCTUA can be used as a support for metal catalysts for various reactions such as hydrogenation and oxidation.
Current State of Research
The research on DCTUA has been increasing in the past decade, with many studies focusing on its synthesis, characterization, and applications. Several studies have reported the synthesis of DCTUA with different DS and the characterization of its physical, chemical, and biological properties. The applications of DCTUA in drug delivery, tissue engineering, biosensors, and catalysis have been explored, with promising results. However, the translation of DCTUA from laboratory research to commercial products is still limited, and further studies are needed to address the challenges such as scale-up, cost-effectiveness, and regulatory approval.
Potential Implications in Various Fields of Research and Industry
The potential implications of DCTUA in various fields of research and industry are vast and promising. In drug delivery, DCTUA can provide a safe and effective carrier for hydrophobic drugs that are poorly soluble and bioavailable. It can also enhance the selectivity and specificity of drug delivery systems by targeting specific cells and tissues. In tissue engineering, DCTUA can provide a biomimetic and biocompatible scaffold for cell growth and tissue regeneration. It can also enhance the mechanical properties, elasticity, and porosity of the scaffold to mimic the properties of native tissues. In biosensors, DCTUA can provide a stable and robust platform for the immobilization of bio-molecules for sensing applications. It can also enhance the sensitivity and selectivity of the biosensor by controlling the orientation and density of the bio-molecules. In catalysis, DCTUA can provide a support for metal catalysts that increase the efficiency and selectivity of various chemical reactions.
Limitations and Future Directions
Despite the promising properties and applications of DCTUA, there are some limitations and challenges that need to be addressed. The synthesis of DCTUA is still limited to laboratory scale, and the scale-up to industrial production is challenging due to the high cost and complexity of the process. The toxicity and safety of DCTUA in long-term exposure and environmental contamination need further investigation. The stability and biodegradability of DCTUA in various applications need to be optimized to maximize the efficacy and minimize the side effects. The compatibility and interaction of DCTUA with other drugs, polymers, and biomolecules need to be studied to enhance the synergistic effects and minimize the adverse effects.
Future directions for the research on DCTUA include:
1. Developing more efficient and sustainable methods for the synthesis of DCTUA, such as green chemistry and biocatalysis.
2. Investigating the toxicity and safety of DCTUA in long-term exposure and environmental contamination, and developing guidelines for its safe use and disposal.
3. Optimizing the stability and biodegradability of DCTUA in various applications, such as drug delivery and tissue engineering, to improve the efficacy and safety of the products.
4. Studying the compatibility and interaction of DCTUA with other drugs, polymers, and biomolecules, to enhance the synergistic effects and minimize the adverse effects.
5. Exploring new applications of DCTUA in emerging fields such as regenerative medicine, gene therapy, and nanotechnology, to expand its potential impact in various industries.
Conclusion
In conclusion, D-Cellotriose Undecaacetate is a promising material derived from cellulose, with unique physical, chemical, and biological properties that make it suitable for various applications in research and industry. Its synthesis, characterization, and analytical methods have been extensively studied, and its potential implications in drug delivery, tissue engineering, biosensors, and catalysis have been explored.
CAS Number | 17690-94-7 |
Product Name | D-Cellotriose Undecaacetate |
IUPAC Name | [(2R,3R,4S,5R,6S)-4,5-diacetyloxy-6-[(2R,3R,4S,5R)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxy-3-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate |
Molecular Formula | C₄₀H₅₄O₂₇ |
Molecular Weight | 966.84 |
InChI | InChI=1S/C40H54O27/c1-15(41)52-12-26-29(55-18(4)44)32(56-19(5)45)36(60-23(9)49)39(64-26)67-31-28(14-54-17(3)43)65-40(37(61-24(10)50)34(31)58-21(7)47)66-30-27(13-53-16(2)42)63-38(62-25(11)51)35(59-22(8)48)33(30)57-20(6)46/h26-40H,12-14H2,1-11H3/t26-,27-,28-,29-,30-,31-,32+,33+,34+,35-,36-,37-,38?,39+,40+/m1/s1 |
SMILES | CC(=O)OCC1C(C(C(C(O1)OC2C(OC(C(C2OC(=O)C)OC(=O)C)OC(=O)C)COC(=O)C)OC(=O)C)OC(=O)C)OC3C(C(C(C(O3)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C |
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