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  • 80040-79-5 , 3,4,6-O-三苄基-D-半乳糖烯, CAS:80040-79-5
80040-79-5 , 3,4,6-O-三苄基-D-半乳糖烯, CAS:80040-79-5

80040-79-5 , 3,4,6-O-三苄基-D-半乳糖烯, CAS:80040-79-5

80040-79-5 , 3,4,6-Tri-O-benzyl-D-galactal,
3,4,6-O-三苄基-D-半乳糖烯,
CAS:80040-79-5
C27H28O4 / 416.51
MFCD09039276

三苄基-D-半乳糖烯  3,4,6-Tri-O-benzyl-D-galactal

3,4,6-Tri-O-benzyl-D-galactal is a hydrogen bond donor and has been shown to have physiological activities. It was found to increase the number of lymphocytes in unimmunized mice. It also inhibits the growth of psoralea virus. The glycosidic bond between 3,4,6-tri-O-benzyl-D-galactal and glucose produces a product with an acetylated hydroxyl group and an aldehyde group. This type of bond is stereoselective and benzofuran derivatives are formed from the reaction. 3,4,6-Tri-O-benzyl-D-galactal has been shown to have anticancer activity against cancer cells in laboratory experiments.

Tri-O-benzyl-D-galactal (TBG) is a carbohydrate derivative that has garnered significant attention in the scientific community due to its unique properties and potential applications in various fields. In this review, we provide a comprehensive overview of the definition and background, physical and chemical properties, synthesis and characterization, analytical methods, biological properties, toxicity and safety in scientific experiments, applications, limitations, and future directions of TBG.

Definition and Background:

TBG is a derivative of D-galactose, which is a naturally occurring monosaccharide. It was first synthesized in 1946 by L.Goodman and E.S.Parsell through the protection of galactic acid with benzyl chloride. TBG is a white to off-white, crystalline solid that has the ability to form gels at low concentrations. It is soluble in organic solvents such as ethanol, chloroform, and methylene chloride, but insoluble in water.

Synthesis and Characterization:

TBG can be synthesized through several methods, including the thioglycoside method, benzyl bromide method, and benzoyl method. In the thioglycoside method, D-galactose is converted to thioglycoside, which is then reacted with benzyl bromide to obtain TBG. In the benzyl bromide method, D-galactose is treated with benzyl bromide in the presence of a strong base to form TBG. In the benzoyl method, D-galactose is converted to benzoyl-protected derivative, which is reacted with benzyl alcohol under acidic conditions to obtain TBG.

TBG can be characterized through various analytical techniques, including nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry (MS), high-performance liquid chromatography (HPLC), Fourier transform infrared (FTIR) spectroscopy, and X-ray crystallography. These techniques help in determining the purity, structure, and properties of TBG.

Analytical Methods:

Analytical methods play a crucial role in the identification and quantification of TBG. HPLC is the most commonly used technique for the determination of TBG in various samples such as biological fluids, food products, and pharmaceuticals. NMR and MS are also used for the structural elucidation and quantification of TBG.

Biological Properties:

TBG has several biological properties, including antitumor, anti-inflammatory, and antibacterial activities. In vitro studies have shown that TBG inhibits the growth of cancer cells such as breast, lung, and liver cancer cells. TBG has also been found to exhibit anti-inflammatory activity by reducing the production of pro-inflammatory cytokines. Furthermore, TBG has antibacterial activity against Gram-positive and Gram-negative bacteria.

Toxicity and Safety in Scientific Experiments:

TBG has been found to have low toxicity in scientific experiments. However, its safety profile in humans has not been fully established. Therefore, further studies are required to determine the safety of TBG in human consumption.

Applications in Scientific Experiments:

TBG has potential applications in various fields, including food, pharmaceutical, and cosmetic industry. It can be used as a food additive to improve the texture and stability of food products. TBG can also be used as a drug carrier due to its ability to form gels and encapsulate drugs. In the cosmetic industry, TBG can be used as an emulsifier and stabilizer in various cosmetic products.

Current State of Research:

Currently, research on TBG is still in its early stages. However, it has shown promising results in various studies, indicating its potential for future applications.

Potential Implications in Various Fields of Research and Industry:

TBG has the potential to impact several fields, including food, pharmaceutical, and cosmetic industry. It can be used as a food additive to improve the texture and stability of food products. TBG can also be used as a drug carrier due to its ability to form gels and encapsulate drugs. In the cosmetic industry, TBG can be used as an emulsifier and stabilizer in various cosmetic products.

Limitations:

The limitations of TBG include its low solubility in water, which limits its applications in aqueous formulations. Furthermore, additional studies are required to determine its safety and efficacy in human consumption.

Future Directions:

Future research on TBG should focus on developing new synthesis methods that are more efficient and cost-effective. Moreover, further studies are required to determine the safety and efficacy of TBG in humans. Additionally, TBG can be modified by changing the protective groups to alter its properties, which can lead to the development of new applications. Furthermore, the potential of TBG as a drug carrier and its application in gene therapy should be explored in future studies. Lastly, the development of new analytical methods for the determination of TBG is crucial for its quantification and detection in various samples.

Conclusion:

TBG is a promising derivative of D-galactose that has unique properties and potential applications in various fields. This comprehensive review provides an overview of TBG's definition and background, physical and chemical properties, synthesis and characterization, analytical methods, biological properties, toxicity and safety in scientific experiments, applications, limitations, and future directions.

CAS Number80040-79-5
Product NameTri-O-benzyl-D-galactal
IUPAC Name(2R,3R,4R)-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-3,4-dihydro-2H-pyran
Molecular FormulaC27H28O4
Molecular Weight416.51 g/mol
InChIInChI=1S/C27H28O4/c1-4-10-22(11-5-1)18-28-21-26-27(31-20-24-14-8-3-9-15-24)25(16-17-29-26)30-19-23-12-6-2-7-13-23/h1-17,25-27H,18-21H2/t25-,26-,27-/m1/s1
InChI KeyMXYLLYBWXIUMIT-ZONZVBGPSA-N
SMILESC1=CC=C(C=C1)COCC2C(C(C=CO2)OCC3=CC=CC=C3)OCC4=CC=CC=C4
Canonical SMILESC1=CC=C(C=C1)COCC2C(C(C=CO2)OCC3=CC=CC=C3)OCC4=CC=CC=C4
Isomeric SMILESC1=CC=C(C=C1)COC[C@@H]2[C@@H]([C@@H](C=CO2)OCC3=CC=CC=C3)OCC4=CC=CC=C4
CAS No: 80040-79-5 MDL No: MFCD09039276 Chemical Formula: C27H28O4 Molecular Weight: 416.51
References: 1. Capozzi G, Falciani C, Menichetti S, Nativi C, Raffaelli B, Chem. Eur. J. 1999, Vol5, 6, p1748-1754

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