34948-79-3 , 三-O-苯甲酰基-D-半乳糖烯,
tri-O-benzoyl-D-galactal ,
CAS:34948-79-3
C27H22O7 / 458.47
三-O-苯甲酰基-D-半乳糖烯,
Tri-O-benzoyl-D-galactal, also known as TBG, is a synthetic chemical compound that belongs to the class of carbohydrates. It is a derivative of D-galactal, a six-carbon monosaccharide, and has three benzoyl groups attached to its hydroxyl groups at positions 2,3,4. TBG, along with other derivatives of D-galactose, has shown promising applications in the field of medicinal chemistry, material science, and nanotechnology.
Synthesis and Characterization
TBG can be synthesized by several methods, but the most common one involves the benzoylation of D-galactose using benzoyl chloride or benzoyl anhydride in the presence of a base such as pyridine or triethylamine. The yield of TBG synthesis varies from 50-80%. The purity of TBG can be confirmed by nuclear magnetic resonance spectroscopy (NMR), high-performance liquid chromatography (HPLC), and mass spectrometry (MS).
Analytical Methods
TBG can be analyzed by several analytical techniques, including NMR, HPLC, MS, Fourier-transform infrared spectroscopy (FTIR), and X-ray crystallography. These methods provide information about the purity, structure, and molecular weight of TBG.
Biological Properties
TBG has been shown to exhibit antitumor, anti-inflammatory, and anti-microbial activities. It inhibits the proliferation of tumor cells by inducing apoptosis and autophagy. TBG also inhibits the production of pro-inflammatory cytokines and chemokines in lipopolysaccharide (LPS)-stimulated macrophages. Furthermore, TBG shows promising activity against bacteria, fungi, and viruses.
Toxicity and Safety in Scientific Experiments
TBG is relatively safe for scientific experiments, with no severe side effects reported so far. However, in vitro studies have shown that TBG can induce cell cycle arrest and apoptosis in human liver carcinoma cells at high concentrations. Therefore, the toxicity of TBG needs to be evaluated further before its application in humans.
Applications in Scientific Experiments
TBG has several potential applications in scientific experiments, including drug delivery, biomaterials, nanotechnology, and molecular recognition. It can be used as a building block for the synthesis of carbohydrate-based nanoparticles, which can be used for targeted drug delivery. TBG can also be used to modify the surface of biomaterials, such as implants and scaffolds, to improve their biocompatibility. Moreover, TBG can be used as a scaffold for the synthesis of molecular recognition materials that can selectively bind to specific biomolecules.
Current State of Research
Currently, several research groups are working on the synthesis, characterization, and application of TBG and its derivatives. They are exploring the potential of TBG in the fields of drug delivery, material science, and biotechnology. Moreover, ongoing research has shown that TBG derivatives can act as potent anti-cancer drugs and can selectively target cancer cells while sparing healthy cells.
Potential Implications in Various Fields of Research and Industry
TBG and its derivatives have several potential implications in various fields of research and industry. For instance, they can be utilized in the development of targeted drug delivery systems, biosensors, and molecular recognition materials. Furthermore, TBG can be used to modify the surface of biomaterials to improve their biocompatibility and to synthesize smart materials, such as stimuli-responsive hydrogels.
Limitations and Future Directions
Despite the potential applications of TBG, some limitations need to be addressed. For example, the synthesis of TBG is a multi-step process and involves the use of toxic reagents, raising concerns about the scalability and toxicity of the synthesis. Furthermore, TBG's poor solubility in water limits its application as a drug delivery agent.
Future directions for TBG research include the development of new methods for the synthesis of TBG and its derivatives using green chemistry approaches. Moreover, the utilization of TBG and its derivatives in the development of multifunctional materials, such as biocompatible electrodes and wearable sensors, holds great promise. Additionally, the investigation of the mechanism of action of TBG in cancer cells and the development of TBG-based therapeutic agents is an exciting area of research.
In conclusion, TBG and its derivatives have great potential in various fields of research and industry. The synthesis, characterization, and application of TBG derivatives are the subjects of current research. Future research directions include the development of new synthetic routes, the exploration of TBG's mechanism of action on cancer cells, and the utilization of TBG and its derivatives in the development of multifunctional materials.
CAS Number | 34948-79-3 |
Product Name | Tri-O-benzoyl-D-galactal |
IUPAC Name | [(2R,3R,4R)-3,4-dibenzoyloxy-3,4-dihydro-2H-pyran-2-yl]methyl benzoate |
Molecular Formula | C27H22O7 |
Molecular Weight | 458.47 g/mol |
InChI | InChI=1S/C27H22O7/c28-25(19-10-4-1-5-11-19)32-18-23-24(34-27(30)21-14-8-3-9-15-21)22(16-17-31-23)33-26(29)20-12-6-2-7-13-20/h1-17,22-24H,18H2/t22-,23-,24-/m1/s1 |
InChI Key | OZFFEFRJEYIEGH-WXFUMESZSA-N |
SMILES | C1=CC=C(C=C1)C(=O)OCC2C(C(C=CO2)OC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4 |
Canonical SMILES | C1=CC=C(C=C1)C(=O)OCC2C(C(C=CO2)OC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4 |
Isomeric SMILES | C1=CC=C(C=C1)C(=O)OC[C@@H]2[C@@H]([C@@H](C=CO2)OC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4 |
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