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604-68-2 , Alpha-D-Glucose pentaacetate, CAS:604-68-2

604-68-2 , Alpha-D-Glucose pentaacetate, CAS:604-68-2
C16H22O11 / 390.34



1,2,3,4,6-Penta-O-acetyl-a-D-glucopyranose is a chemical compound that is an ester of the sugar penta-O-acetyl-a-D-glucopyranose and acetic acid. It has been shown to inhibit the activity of a number of enzymes, including proteins such as phospholipases C and D and fatty acid synthetases. The 1,2,3,4,6-penta-O-acetyl analogues have been shown to be effective in inhibiting model systems for the pathogenesis of inflammatory bowel disease and cancer. The hydroxyl group on the sugar ring may be important for binding to these enzymes.

Alpha-D-Glucose pentaacetate is a derivative of glucose, which is commonly found in nature. It is a white crystalline substance that is soluble in most solvents, except for water. Alpha-D-Glucose pentaacetate is used extensively in scientific experiments due to its unique physical and chemical properties. In this paper, we will look at various aspects of alpha-D-Glucose pentaacetate, including its definition and background, physical and chemical properties, synthesis, characterization, analytical methods, biological properties, toxicity, safety in scientific experiments, applications, current state of research, potential implications in various fields of research and industry, limitations, and future directions.

Definition and Background

Alpha-D-Glucose pentaacetate is a carbohydrate that is derived by acetylating the five hydroxyl groups of glucose with acetic anhydride. It was first synthesized in 1902 by Emil Fischer and Rudolph Boehm. Alpha-D-Glucose pentaacetate is commonly used as an intermediate in the synthesis of other organic compounds, such as steroids, antibiotics, and alkaloids.

Physical and Chemical Properties

Alpha-D-Glucose pentaacetate is a white crystalline solid that has a melting point of 107°C. It is soluble in most organic solvents, such as methanol, ethanol, acetone, and chloroform. However, it is insoluble in water. Alpha-D-Glucose pentaacetate is a stable compound that can be stored for long periods of time without any significant degradation.

Synthesis and Characterization

Alpha-D-Glucose pentaacetate can be synthesized by acetylating glucose with acetic anhydride in the presence of a catalyst. The product can be purified by recrystallization from an organic solvent. The chemical structure of alpha-D-Glucose pentaacetate can be confirmed using various spectroscopic techniques, such as infrared spectroscopy, nuclear magnetic resonance spectroscopy, and mass spectrometry.

Analytical Methods

Several analytical methods have been developed to determine the purity, identity, and concentration of alpha-D-Glucose pentaacetate. These methods include high-performance liquid chromatography, gas chromatography, and melting point determination.

Biological Properties

Alpha-D-Glucose pentaacetate has been shown to exhibit antiviral, antimicrobial, and anti-inflammatory properties. It has also been shown to inhibit the growth of cancer cells in vitro. However, its biological activity in vivo is still under investigation.

Toxicity and Safety in Scientific Experiments

Alpha-D-Glucose pentaacetate is considered to be relatively safe for use in scientific experiments. However, it can be toxic if ingested or inhaled in large amounts. Therefore, appropriate safety precautions should be taken when handling the compound.

Applications in Scientific Experiments

Alpha-D-Glucose pentaacetate is widely used as an intermediate in the synthesis of other organic compounds. It is also used as a protective agent for the synthesis of several important molecules. In addition, it is used as a solvent for various reactions. Its unique physical and chemical properties make it an important compound in synthetic organic chemistry.

Current State of Research

Research on alpha-D-Glucose pentaacetate is ongoing in several fields, including organic chemistry, biochemistry, pharmaceuticals, and materials science. Recent studies have focused on synthesizing derivatives of alpha-D-Glucose pentaacetate that exhibit enhanced biological activity and biocompatibility.

Potential Implications in Various Fields of Research and Industry

Alpha-D-Glucose pentaacetate has the potential to be used in several fields, including drug discovery, materials science, and nanotechnology. Its ability to inhibit the growth of cancer cells makes it a promising candidate for the development of new anticancer drugs. In addition, its unique physical and chemical properties make it an attractive material for the development of new materials with novel properties.

Limitations and Future Directions

One of the main limitations of alpha-D-Glucose pentaacetate is its solubility in water. Future research could focus on developing new techniques to increase its solubility in aqueous solvents. Other future directions could include improving the biological activity and biocompatibility of alpha-D-Glucose pentaacetate derivatives. In addition, research could focus on using alpha-D-Glucose pentaacetate in the development of new materials with advanced properties, such as enhanced mechanical strength or electrical conductivity.


In conclusion, alpha-D-Glucose pentaacetate is an important compound in organic chemistry that exhibits unique physical and chemical properties. It is widely used in scientific experiments as an intermediate in the synthesis of other organic compounds. Its biological activity, toxicity, safety, applications, and potential implications in various fields of research and industry have been discussed in this paper. Further research will be required to fully explore the potential of alpha-D-Glucose pentaacetate in various fields.

CAS Number604-68-2
Product Namealpha-D-Glucose pentaacetate
IUPAC Name[(2R,3R,4S,5R,6R)-3,4,5,6-tetraacetyloxyoxan-2-yl]methyl acetate
Molecular FormulaC16H22O11
Molecular Weight390.34 g/mol
Synonyms1,2,3,4,6-penta-O-acetyl-alpha-D-glucopyranoside, beta-D-glucose pentaacetate, glucose pentaacetate, glucose pentaacetate, (alpha-D)-isomer, glucose pentaacetate, (beta-(D))-isomer, glucose pentaacetate, (D)-isomer, penta-O-acetyl-alpha-D-glucopyranose, penta-O-acetylglucopyranose
Canonical SMILESCC(=O)OCC1C(C(C(C(O1)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
Isomeric SMILESCC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C

CAS No: 604-68-2 Synonyms: a-D-Glucose pentaacetate MDL No: MFCD00064071 Chemical Formula: C16H22O11 Molecular Weight: 390.34

Product name: Alpha-1,2,3,4,6-Pentacetyl-D-glucose; Alpha-D-Glucose pentaacetate                                    

CAS: 604-68-2     M.F.C16H22O11       M.W.: 390.34      Batch No: 20080704





White crystal powder



soluble in CHCl3, insoluble water



IR and TLC


Melting point

107  ~  110°C

108 ~ 111 

Specific rotation

[a]D/20 (c=1, CHCl3)

+100 ~  +104o


Water content (K.F.)



Residue on ignition

Max. 1%



Should be one spot

One spot




Assay (HPLC)*

Min. 98%


*The stationary phase is C18 colum , the mobile phase is water-methol (V : V = 6 : 4) and the detecting wave length is 210nm.


1. Haikal AZ, El Ashry ESH, Banoub J, Carbohydr. Res. 2003, Vol338, No22, p2291-2299


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