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216971-58-3 ,3-Indolyl-b-D-glucuronide cyclohexylammonium salt,CAS:216971-58-3

216971-58-3 ,3-Indolyl-b-D-glucuronide cyclohexylammonium salt,
CAS:216971-58-3
C14H15NO7·C6H13N / 408.45
MFCD00083390

3-Indolyl b-D-glucuronide cyclohexylammonium salt

3-吲哚-beta-D-葡萄糖醛酸苷环己胺盐

Indoxylbeta-D-glucuronidecyclohexylammonium salt: Definition, Properties, Synthesis and Characterization, Analytical Methods, Biological Properties and Applications

Definition and Background:

Indoxylbeta-D-glucuronidecyclohexylammonium salt, or simply Indoxyl glucuronide, is a biochemical compound that belongs to a group of indoles. It is considered an important metabolite of the stress hormone cortisol, and can be found in the urine and feces of humans and animals. It is also produced by the fermentation of tryptophan in the intestinal tract of animals, which makes it an important biomarker for assessing the functional status of the intestinal microbiome.

Physical and Chemical Properties:

Indoxyl glucuronide is an odorless, white crystalline powder that is soluble in water and organic solvents, such as ethanol and dimethyl sulfoxide. It has a molecular weight of 409.5 g/mol and a melting point of 238°C. It is stable under normal conditions of storage and handling and does not degrade when exposed to light or air.

Synthesis and Characterization:

Indoxyl glucuronide can be synthesized using a variety of chemical methods, including the reaction of indole-3-acetic acid with glucuronic acid, or the reaction of indoxyl with the beta-glucuronidase enzyme. The resulting compound can be characterized using a wide range of analytical techniques, such as nuclear magnetic resonance spectroscopy, infrared spectroscopy, and mass spectrometry.

Analytical Methods:

Indoxyl glucuronide can be measured using various analytical methods, including high-performance liquid chromatography, gas chromatography, and liquid chromatography-mass spectrometry. These methods are highly sensitive and can detect low concentrations of indoxyl glucuronide in biological fluids such as urine and feces.

Biological Properties:

Indoxyl glucuronide has been shown to have several biological properties, including anti-inflammatory and anti-oxidant activities. It is also an important biomarker for assessing the health of the intestinal microbiome, as changes in its levels have been associated with various gastrointestinal disorders, such as inflammatory bowel disease and colorectal cancer.

Toxicity and Safety in Scientific Experiments:

Several studies have investigated the potential toxicity of indoxyl glucuronide in various animal models, and have found that it is relatively safe at therapeutic doses. However, higher doses have been associated with adverse effects, such as liver and kidney damage.

Applications in Scientific Experiments:

Indoxyl glucuronide has several applications in scientific experiments, including the assessment of the functional status of the intestinal microbiome, the evaluation of the efficacy of novel treatments for gastrointestinal disorders, and the development of new diagnostic tools for colorectal cancer.

Current State of Research:

Research into the biological properties and applications of indoxyl glucuronide is ongoing, with several studies investigating its potential as a biomarker for predicting the risk of colorectal cancer, its role in regulating the immune response, and its potential therapeutic applications in cancer and other diseases.

Potential Implications in Various Fields of Research and Industry:

Indoxyl glucuronide has potential implications in various fields of research and industry, including the development of new diagnostic tools and therapies for gastrointestinal disorders, the optimization of animal nutrition, and the production of biofuels and other renewable resources.

Future Directions:

Some possible future directions for research on indoxyl glucuronide include:

- Developing new analytical methods for measuring its levels in biological fluids.

- Investigating its potential as a predictive biomarker for colorectal cancer.

- Identifying the molecular mechanisms underlying its anti-inflammatory and anti-oxidant activities.

- Developing novel therapeutic approaches targeting indoxyl glucuronide and its associated pathways.

- Studying the interplay between indoxyl glucuronide and the intestinal microbiome, and its impact on human health and disease.

- Utilizing indoxyl glucuronide as a biosensor for environmental monitoring and industrial applications.

CAS Number216971-58-3
Product NameIndoxylbeta-D-glucuronidecyclohexylammoniumsalt
IUPAC Namecyclohexanamine;(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(1H-indol-3-yloxy)oxane-2-carboxylic acid
Molecular FormulaC20H28N2O7
Molecular Weight408.4 g/mol
InChIInChI=1S/C14H15NO7.C6H13N/c16-9-10(17)12(13(19)20)22-14(11(9)18)21-8-5-15-7-4-2-1-3-6(7)8;7-6-4-2-1-3-5-6/h1-5,9-12,14-18H,(H,19,20);6H,1-5,7H2/t9-,10-,11+,12-,14+;/m0./s1
InChI KeyYGIPNZMTCTUCAX-CYRSAHDMSA-N
SMILESC1CCC(CC1)N.C1=CC=C2C(=C1)C(=CN2)OC3C(C(C(C(O3)C(=O)O)O)O)O
Synonymsindoxyl glucuronide, indoxyl-beta-D-glucuronide
Canonical SMILESC1CCC(CC1)N.C1=CC=C2C(=C1)C(=CN2)OC3C(C(C(C(O3)C(=O)O)O)O)O
Isomeric SMILESC1CCC(CC1)N.C1=CC=C2C(=C1)C(=CN2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)C(=O)O)O)O)O

CAS No: 35804-66-1,216971-58-3 Synonyms: Indoxyl b-D-glucuronide CHX saltIBDG MDL No: MFCD00083390  Chemical Formula: C14H15NO7·C6H13N Molecular Weight: 408.45


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