Potassium indol-3-yl sulfate
[CAS# 2642-37-7]

Identification

• Classification: Inorganic chemical industry >> Inorganic salt >> Metal sulfides and sulfates
• Name: Potassium indol-3-yl sulfate
• Synonyms: Indol-3-ol, potassium sulfate; Indol-3-yl sulfate, potassium salt; Indoxyl sulfate potassium salt
• Molecular Formula: C₈H₆NO₄S^.K
• Molecular Weight: 251.30
• CAS Registry Number: 2642-37-7
• EC Number: 220-145-5
• SMILES: C1=CC=C2C(=C1)C(=CN2)OS(=O)(=O)[O-].[K+]

Properties

• Melting point: 165 ºC (Decomposes) (Expl.)

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P280-P301+P312-P302+P352-P305+P351+P338

Discovory and Applicatios

Potassium indol-3-yl sulfate is an organic salt derived from the sulfation of indole at the 3-position, forming the indol-3-yl sulfate anion paired with potassium as the counterion. This compound belongs to the class of indole derivatives, which are widespread in biological systems and have significant roles in various biochemical processes.

The discovery of potassium indol-3-yl sulfate is linked to studies on the metabolism of tryptophan, an essential amino acid that undergoes complex biochemical transformations in organisms. One of the metabolic pathways involves the formation of indole compounds, which can be further modified by sulfation to increase their water solubility and facilitate excretion. Potassium indol-3-yl sulfate is one such metabolite observed in biological fluids, particularly in urine, where it serves as a biomarker for certain physiological and pathological conditions.

In biological systems, the sulfation of indole compounds, including indol-3-yl sulfate, is catalyzed by sulfotransferase enzymes, which transfer a sulfate group from the donor molecule 3'-phosphoadenosine-5'-phosphosulfate (PAPS) to the hydroxyl or amino group of the substrate. This modification significantly alters the physicochemical properties of indole derivatives, enhancing their hydrophilicity and reducing their toxicity.

The application of potassium indol-3-yl sulfate extends to analytical and clinical chemistry, where it is used as a reference compound for detecting and quantifying indole sulfates in biological samples. Its presence and concentration can provide valuable information about liver and kidney function, gut microbiota activity, and the metabolism of tryptophan and related compounds. Elevated levels of indol-3-yl sulfate have been associated with certain diseases, including chronic kidney disease, making it an important molecule in medical diagnostics.

In addition to its biological significance, potassium indol-3-yl sulfate is also utilized in research focused on understanding the role of indole metabolites in cellular signaling and inter-organ communication. Studies have shown that indole sulfates can influence immune responses, oxidative stress, and inflammatory pathways, highlighting their potential as targets for therapeutic intervention.

From a chemical perspective, potassium indol-3-yl sulfate is characterized by its ionic nature and solubility in aqueous solutions, making it suitable for various experimental applications. It can be synthesized by the chemical sulfation of indole derivatives followed by neutralization with potassium hydroxide to form the potassium salt.

Overall, potassium indol-3-yl sulfate represents a biologically and chemically important molecule with applications in metabolism research, clinical diagnostics, and the study of indole-related biochemical pathways. Its role as a metabolite of tryptophan highlights the intricate connections between diet, microbiota, and human health, emphasizing the compound's relevance in both basic and applied sciences.

References

2012. Protein-bound uremic toxins in hemodialysis patients measured by liquid chromatography/tandem mass spectrometry and their effects on endothelial ROS production. Analytical and Bioanalytical Chemistry, 403(7).
DOI: 10.1007/s00216-012-5929-3

2013. Triggering of suicidal erythrocyte death by uremic toxin indoxyl sulfate. BMC Nephrology, 14(1).
DOI: 10.1186/1471-2369-14-244

2023. Incorporating Uremic Solute-mediated Inhibition of OAT1/3 Improves PBPK Prediction of Tenofovir Renal and Systemic Disposition in Patients with Severe Kidney Disease. Pharmaceutical Research, 40(10).
DOI: 10.1007/s11095-023-03594-x