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467214-46-6 , Chloro-3-indolyl a-D-glucopyranoside, Salmon a-glucoside; 6-Chloro-3-(a-D-glucopyranosyloxy)indole

Cas:467214-46-6 ,
Chloro-3-indolyl a-D-glucopyranoside,
Salmon a-glucoside; 6-Chloro-3-(a-D-glucopyranosyloxy)indole
C14H16ClNO6 / 329.73

Chloro-3-indolyl a-D-glucopyranoside

Salmon a-glucoside; 6-Chloro-3-(a-D-glucopyranosyloxy)indole

6-Chloro-3-indoxyl-alpha-D-glucopyranoside: Definition and Background

6-Chloro-3-indoxyl-alpha-D-glucopyranoside is a synthetic compound used in a variety of scientific experiments. It is also known as X-Gluc or 5-bromo-4-chloro-3-indolyl-beta-D-glucopyranoside, and it is commonly used as a substrate for the detection of beta-glucuronidase activity. Beta-glucuronidase is an enzyme that is commonly found in bacteria and some eukaryotic cells. Bacteria often use beta-glucuronidase to break down complex carbohydrates for energy. Furthermore, this enzyme is also present in certain insects, plants, and animals.

Physical and Chemical Properties

6-Chloro-3-indoxyl-alpha-D-glucopyranoside is typically available in the form of a white powder. It has a molecular weight of 408.83 g/mol and a melting point of 190°C. It is soluble in dimethyl sulfoxide (DMSO) and has a solubility of 50 mg/mL in water at room temperature. This compound can be purchased from various chemical suppliers and is often used in combination with other chemicals for scientific experiments.

Synthesis and Characterization

The synthesis of 6-Chloro-3-indoxyl-alpha-D-glucopyranoside involves the use of several chemical reagents and steps. Firstly, 5-chloro-3-indolyl-beta-D-glucopyranoside and p-toluenesulfonic acid monohydrate are combined in a mixture of chloroform and water. Next, the mixture is heated and stirred under nitrogen gas. After several hours, the mixture is cooled and filtered to remove any impurities. The resulting compound is then treated with sodium azide and heated under reflux temperature. Finally, the compound is purified using column chromatography, and the final product is obtained.

Analytical Methods

Several analytical methods can be used to detect the presence of 6-Chloro-3-indoxyl-alpha-D-glucopyranoside in scientific experiments. These methods include Ultraviolet-visible (UV-vis) spectrophotometry, chromatography, and mass spectrometry. UV-vis spectrophotometry is the most common method used to detect the presence of this compound. This method involves measuring the absorbance of light in the ultraviolet-visible range, which corresponds to the dye created when 6-Chloro-3-indoxyl-alpha-D-glucopyranoside hydrolyzes with beta-glucuronidase. Chromatography is another commonly used method which involves separating 6-Chloro-3-indoxyl-alpha-D-glucopyranoside from other compounds, such as impurities or reaction byproducts. Mass spectrometry is also used to detect the formation of the X-Gluc dye.

Biological Properties

Beta-glucuronidase, the enzyme targeted by 6-Chloro-3-indoxyl-alpha-D-glucopyranoside, is ubiquitous, and the compound can be used in a variety of biological assays. One example of the compound's biological activity is its use in the detection of E. coli in wastewater. In this case, X-Gluc serves as a substrate for beta-glucuronidase activity in E. coli, generating a blue stain indicative of the presence of E. coli. Additionally, X-Gluc is used in the detection of transgene expression in genetically modified plants.

Toxicity and Safety in Scientific Experiments

6-Chloro-3-indoxyl-alpha-D-glucopyranoside has been reported to have low toxicity in scientific experiments. It is not classified as a hazardous substance by any major regulatory agency, including the United States Environmental Protection Agency (EPA) and the European Chemicals Agency (ECHA). Nonetheless, appropriate laboratory safety measures, including the use of personal protective equipment and adequate ventilation, should be taken when handling the compound.

Applications in Scientific Experiments

6-Chloro-3-indoxyl-alpha-D-glucopyranoside has several applications in scientific experiments. Some of these applications include:

- Beta-glucuronidase assays in microbiology and genetic engineering

- Detection of E. coli in contaminated water samples

- Visualization of transgene expression in genetically modified plants

Current State of Research

The scientific community has extensively studied 6-Chloro-3-indoxyl-alpha-D-glucopyranoside, revealing its potential as a robust substrate in a variety of assays. The compound is widely used in microbiology and its applications span many fields of research, including biotechnology, environmental science, and food safety. There is still ongoing research on developing new compounds with a structure similar to X-Gluc to optimize its properties for certain applications, as well as to understand the mechanisms involved in the formation of the blue dye created when 6-Chloro-3-indoxyl-alpha-D-glucopyranoside hydrolyzes with beta-glucuronidase.

Potential Implications in Various Fields of Research and Industry

6-Chloro-3-indoxyl-alpha-D-glucopyranoside has significant implications in various fields of research and industry. For instance, it can be used to detect E. coli in water samples, making it highly relevant in the field of environmental science. Additionally, it has been shown to be useful in detecting recombinant gene expression in plants, making it a valuable tool in genetics and biotechnology. 6-Chloro-3-indoxyl-alpha-D-glucopyranoside can also be used in food safety applications to detect bacteria and ensure the safety of food products.

Limitations and Future Directions

While 6-Chloro-3-indoxyl-alpha-D-glucopyranoside has proven to be useful in many assays, it has some limitations. For instance, it may not be compatible with certain assay conditions or detection methods. Additionally, its blue color can sometimes be obscured by other compounds, limiting its utility in certain experiments. Future research in this area could focus on developing new substrates that are more sensitive and more reliable than 6-Chloro-3-indoxyl-alpha-D-glucopyranoside for beta-glucuronidase detection. Alternatively, researchers could optimize the current methods used for X-Gluc assay analysis to overcome these limitations.

Future Directions

- Development of improved methods for detecting beta-glucuronidase activity

- Synthesis of new substrates with higher sensitivity and specificity

- Advancements in the understanding of the biochemical mechanisms of X-Gluc hydrolysis

- Use of X-Gluc and related compounds in cell imaging, including for in situ detection of beta-glucuronidase activity

- Exploration of potential applications of X-Gluc and beta-glucuronidase activity in cancer research

- Development of new methods for making X-Gluc more detectable in complicated environments like soil and sediment

- Study of new applications of X-Gluc and beta-glucuronidase activity in various test organisms like plants, insects, and fish

CAS Number467214-46-6
Product Name6-Chloro-3-indoxyl-alpha-D-glucopyranoside
IUPAC Name(2R,3R,4S,5S,6R)-2-[(6-chloro-1H-indol-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Molecular FormulaC14H16ClNO6
Molecular Weight329.73 g/mol
Canonical SMILESC1=CC2=C(C=C1Cl)NC=C2OC3C(C(C(C(O3)CO)O)O)O
Isomeric SMILESC1=CC2=C(C=C1Cl)NC=C2O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O


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