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56846-39-0, 4-Nitrophenyl β-D-maltopyranoside, CAS: 56846-39-0

56846-39-0, 4-Nitrophenyl β-D-maltopyranoside, CAS: 56846-39-0
C18H25NO13 / 463.39

4-Nitrophenyl b-D-maltopyranoside

4-Nitrophenyl-beta-D-maltopyranoside (NPG) is a compound used in scientific research as a substrate for enzymes that hydrolyze maltose derivatives. This paper will explore the 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 of NPG.

Definition and Background:

NPG is a synthetic carbohydrate derivative that is widely used in biochemical and enzymatic experiments. It is a substrate for several enzymes, including alpha-glucosidase, beta-glucosidase, and maltase. NPG is an analogue of maltose containing a nitrophenyl group that absorbs light strongly at 405 nm. The hydrolysis of NPG by enzymes produces the yellow 4-nitrophenol, which can be detected spectrophotometrically.

Physical and Chemical Properties:

The molecular formula of NPG is C18H25NO11. It has a molecular weight of 439.4 g/mol. NPG is a crystalline solid that is soluble in water and dimethyl sulfoxide. It has a melting point of 170-175 °C and a specific optical rotation of +9.8°. The compound is stable in neutral and slightly acidic solutions, but it is hydrolyzed by strong alkalis.

Synthesis and Characterization:

The synthesis of NPG involves the reaction of maltose with 4-nitrophenyl alpha-D-glucopyranoside in the presence of an acid catalyst. The reaction results in the formation of NPG and water. The purity and identity of the compound can be confirmed by techniques such as high-performance liquid chromatography (HPLC), mass spectrometry (MS), and nuclear magnetic resonance (NMR) spectroscopy.

Analytical Methods:

NPG can be quantified using spectrophotometric methods, such as UV-visible absorption and fluorescence spectroscopy. These methods are based on the measurement of the absorbance or fluorescence intensity of the 4-nitrophenol product at 405 nm. HPLC and MS can also be used to separate and detect NPG and its hydrolysis products.

Biological Properties:

NPG is a non-toxic compound that is widely used as a substrate for enzyme assays. It is metabolized by several enzymes in the gastrointestinal tract and liver of mammals. NPG has been shown to inhibit the activity of alpha-glucosidase, a key enzyme involved in the digestion of dietary carbohydrates, and this property has been exploited in the development of anti-diabetic drugs.

Toxicity and Safety in Scientific Experiments:

NPG is considered a non-toxic compound that does not pose any significant risk to human health. However, as with any chemical substance, it should be handled with care and proper safety measures should be taken in laboratory experiments.

Applications in Scientific Experiments:

NPG is used as a substrate for enzyme assays in research laboratories. It is particularly useful in the study of carbohydrate metabolism and in the development of enzyme inhibitors. NPG has also been used in the detection and quantification of glycosidases and glucosidases in biological samples.

Current State of Research:

Research on NPG has focused on its potential as a therapeutic agent for the treatment of diabetes and other metabolic disorders. Several studies have shown that NPG can inhibit alpha-glucosidase activity and reduce postprandial blood glucose levels in animal models. NPG has also been investigated for its anti-tumor and anti-inflammatory properties.

Potential Implications in Various Fields of Research and Industry:

NPG has potential applications in the development of novel therapeutics for metabolic disorders, cancer, and inflammation. NPG-based enzyme inhibitors may offer alternative treatments for diseases such as diabetes and cancer. In the food industry, NPG can be used as a sweetener and flavor enhancer.

Limitations and Future Directions:

NPG has some limitations as a substrate for enzyme assays due to its low solubility and tendency to form aggregates. Future research should focus on the development of more soluble and stable derivatives of NPG. Other areas of research include the identification of new enzymes that can hydrolyze NPG and the exploration of NPG's potential in drug delivery and imaging applications.

Future Directions:

1. Development of new derivatives of NPG with improved solubility and stability.

2. Identification of new enzymes that can hydrolyze NPG.

3. Development of new methods for the detection and quantification of glycosidases and glucosidases.

4. Exploration of NPG's potential in drug delivery and imaging applications.

5. Investigation of NPG as a scaffold for the synthesis of new enzyme inhibitors.

6. Development of NPG-based sweeteners and flavor enhancers for the food industry.

7. Evaluation of the safety and efficacy of NPG in human clinical trials.

8. Exploration of the potential of NPG in the treatment of other diseases such as cancer and inflammation.

9. Investigation of the interactions of NPG with enzymes and other biomolecules.

10. Development of NPG-based biosensors for the detection of enzymes and other biomolecules.

CAS Number56846-39-0
Product Name4-Nitrophenyl-beta-D-maltopyranoside
IUPAC Name(2R,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6S)-4,5-dihydroxy-2-(hydroxymethyl)-6-(4-nitrophenoxy)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
Molecular FormulaC18H25NO13
Molecular Weight463.4 g/mol
Canonical SMILESC1=CC(=CC=C1[N+](=O)[O-])OC2C(C(C(C(O2)CO)OC3C(C(C(C(O3)CO)O)O)O)O)O
Isomeric SMILESC1=CC(=CC=C1[N+](=O)[O-])O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O

CAS No: 56846-39-0 MDL No: MFCD00069844 Chemical Formula: C18H25NO13 Molecular Weight: 463.39

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Product name: 4-Nitrophenyl β-D-maltopyranoside

M.F.: C18H25NO13   M.W.: 463.39      CAS:56846-39-0





White powder



Easily soluble in water, insoluble ether


NMR and MS

Should comply





Appearance of solution

Dissolve0.5 gin 10 ml of water,

and the solution should be clear and colorless


Loss weight on drying



Elemental Anal. (%C anhydrous)

46.15 - 47.15 %


Elemental Anal. (%N anhydrous)

2.62 - 3.42 %



Max. 20ppm



One spot

One spot

Assay by HPLC

Min. 98%



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