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  • 22415-91-4 ,  a-D-五苯甲酰基吡喃葡萄糖 , Alpha-D-glucopyranose pentabenzoate , CAS:22415-91-4
22415-91-4 ,  a-D-五苯甲酰基吡喃葡萄糖 , Alpha-D-glucopyranose pentabenzoate , CAS:22415-91-4

22415-91-4 , a-D-五苯甲酰基吡喃葡萄糖 , Alpha-D-glucopyranose pentabenzoate , CAS:22415-91-4

22415-91-4 , Alpha-D-glucopyranose pentabenzoate ,
a-D-五苯甲酰基吡喃葡萄糖,
CAS:22415-91-4
C41H32O11 / 700.69
MFCD00010695

1,2,3,4,6-Penta-O-benzoyl-a-D-glucopyranose

a-D-五苯甲酰基吡喃葡萄糖,

Alpha-D-Glucopyranose pentabenzoate, also known as PGB, is a derivative of alpha-D-glucose that has significant potential in various fields of research and industry. This paper aims to provide a comprehensive overview of PGB, its physical and chemical properties, synthesis, 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.

Definition and Background:

Alpha-D-glucose is a monosaccharide, which is the simplest form of carbohydrate. One of the derivatives of alpha-D-glucose is alpha-D-Glucopyranose pentabenzoate (PGB). PGB is an organic compound that is used in a variety of chemical and biological applications, such as in the synthesis of other compounds, as an analytical tool, and in drug development.

Synthesis and Characterization:

PGB can be synthesized through a variety of methods, including the acylation of alpha-D-glucose with benzoyl chloride using pyridine as a catalyst. The synthesized compound is then purified using column chromatography or recrystallization. Characterization of PGB is typically done using analytical methods, such as NMR spectroscopy, IR spectroscopy, and mass spectrometry.

Analytical Methods:

Analytical methods that are commonly used for the identification and quantification of PGB include high-performance liquid chromatography (HPLC), gas chromatography (GC), and capillary electrophoresis (CE).

Biological Properties:

Studies have shown that PGB can act as an anti-inflammatory agent, reducing the level of pro-inflammatory cytokines and inhibiting the expression of inducible nitric oxide synthase (iNOS). PGB has also displayed potential as an anticancer agent, inhibiting the growth of cancer cells in vitro.

Toxicity and Safety in Scientific Experiments:

PGB has a low toxicity when used in scientific experiments. According to the Material Safety Data Sheet (MSDS), PGB may cause irritation to the eyes, skin, and respiratory tract. However, the MSDS reports no adverse health effects associated with the compound.

Applications in Scientific Experiments:

PGB has been used in a variety of chemical and biological applications, such as in the synthesis of other compounds, as an analytical tool, and in drug development. PGB has been used as an analytical standard in HPLC and GC methods for the analysis of carbohydrates.

Current State of Research:

The current research on PGB is focused on developing new synthetic methods, identifying and testing its biological activities, and exploring its potential applications in drug development and other fields.

Potential Implications in Various Fields of Research and Industry:

PGB has potential implications in various fields of research and industry, including drug development, biotechnology, and materials science. PGB can be used as an intermediate for the synthesis of other compounds, particularly carbohydrate-based pharmaceuticals. PGB can also be used as a chiral building block in the synthesis of other biologically active molecules.

Limitations:

The use of PGB is limited by its low solubility in nonpolar solvents, which can limit its application in some chemical reactions.

Future Directions:

Future research on PGB could focus on improving its solubility, developing new synthetic methods, testing its biological activities further, using PGB to create new materials, and exploring its potential application in various fields of industry. Another future direction for research could be investigating the use of PGB as a precursor for the synthesis of new drugs. Moreover, the use of PGB in agriculture can be an interesting field to explore, given its potential bioactivity as anti-inflammatory and anti-cancer agent.

CAS Number22415-91-4
Product Namealpha-D-Glucopyranose pentabenzoate
IUPAC Name(3,4,5,6-tetrabenzoyloxyoxan-2-yl)methyl benzoate
Molecular FormulaC41H32O11
Molecular Weight700.69 g/mol
InChIInChI=1S/C41H32O11/c42-36(27-16-6-1-7-17-27)47-26-32-33(49-37(43)28-18-8-2-9-19-28)34(50-38(44)29-20-10-3-11-21-29)35(51-39(45)30-22-12-4-13-23-30)41(48-32)52-40(46)31-24-14-5-15-25-31/h1-25,32-35,41H,26H2
InChI KeyJJNMLNFZFGSWQR-UHFFFAOYSA-N
SMILESC1=CC=C(C=C1)C(=O)OCC2C(C(C(C(O2)OC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4)OC(=O)C5=CC=CC=C5)OC(=O)C6=CC=CC=C6
Synonyms1,2,3,4,6-penta-B-alpha-D-M, 1,2,3,4,6-penta-O-benzoyl-alpha-D-mannopyranose, penta-B-alpha-D-mannopyranose
Canonical SMILESC1=CC=C(C=C1)C(=O)OCC2C(C(C(C(O2)OC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4)OC(=O)C5=CC=CC=C5)OC(=O)C6=CC=CC=C6


CAS No: 22415-91-4 MDL No: MFCD00010695 Chemical Formula: C41H32O11 Molecular Weight: 700.69

Product name: Alpha-D-glucopyranose pentabenzoate     CAS: 22415-91-4 

M.F.: C41H32O11    M.W.: 700.69   Batch No: 20080325  Quantity: 100 g 

Items

Standards

Results

Appearance

White crystal powder

Complies

Solubility

insoluble in water, easily soluble CHCl3

Complies

Identification

IR and HPLC

Complies

Melting point

180 - 185 °C

184-185

Specific rotation

[α]20/D (c 1 in CHCl3)

125° - 129°

127.3°

Beta-D-glucopyranose pentabenzoate

Max 1%

Complies, 0.21%

Water

Max. 0.5%

0.2%

Residue on ignition

Max. 0.5%

0.1%

Assay

Min. 98%

98.6%

References:

1. Gros EG, Ondetti MA, Sproviero JO, Deulofeu V, et al., J. Org. Chem. 1962, Vol27, p924
2. Ness RK, Fletcher Jr HG, Hudson CS, J. Am. Chem. Soc. 1950, Vol72, p2200

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