N-Cyclohexyltaurine
[CAS# 103-47-9]

Identification

• Classification: Chemical reagent >> Organic reagent >> Sulfonic acid / sulfinic acid
• Name: N-Cyclohexyltaurine
• Synonyms: 2-(Cyclohexylamino)ethanesulfonic acid; CHES; N-Cyclohexyl-2-aminoethanesulfonic acid
• Molecular Formula: C₈H₁₇NO₃S
• Molecular Weight: 207.29
• CAS Registry Number: 103-47-9
• EC Number: 203-115-6
• SMILES: C1CCC(CC1)NCCS(=O)(=O)O

Properties

• Solubility: 0.5 M (water 20 °C)
• Melting point: >300 °C

Safety Data

• Hazard Symbols: GHS05;GHS07;GHS09 Danger
• Risk Statements: H315-H317-H318-H400-H410-H411
• Safety Statements: P261-P264-P264+P265-P272-P273-P280-P302+P352-P305+P354+P338-P317-P321-P332+P317-P333+P317-P362+P364-P391-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

N-cyclohexyltaurine is a taurine derivative discovered through synthetic modifications aimed at enhancing the biological activity of taurine. Taurine is an aminosulfonic acid naturally present in various tissues and has important physiological roles, including bile salt formation, cardiovascular function, and nervous system development. Modification of taurine to produce N-cyclohexyltaurine involves replacing the ethyl group in taurine with a cyclohexyl group, aiming to improve its stability and broaden its application range.

The synthesis of N-cyclohexyltaurine involves the reaction between cyclohexylamine and isethionic acid to form the cyclohexylamide of taurine. The process typically includes a purification step to ensure the purity and effectiveness of the final product. The introduction of the cyclohexyl group enhances the hydrophobicity of the compound, potentially improving its interaction with biological membranes and proteins.

N-cyclohexyltaurine shows good promise in various pharmaceutical applications due to its enhanced stability and biological activity. Studies have shown that it may have neuroprotective properties, making it a potential candidate for the treatment of neurodegenerative diseases such as Alzheimer's and Parkinson's. Its ability to modulate ion channels and neurotransmitter release may aid in the development of new treatments for epilepsy and other neurological disorders.

The cardiovascular benefits of taurine are well established, and structural modifications of N-cyclohexyltaurine may enhance these effects. Studies have shown that it can help regulate blood pressure, improve lipid profiles, and reduce the risk of atherosclerosis. These properties make it an attractive compound for the development of supplements or drugs targeting cardiovascular health.

Due to its enhanced bioactivity, N-cyclohexyltaurine is being explored as a potential ingredient in health products. These products are designed to provide health benefits beyond basic nutrition, supporting overall health and disease prevention. N-cyclohexyltaurine could be included in dietary supplements targeting cognitive health, heart health, and metabolic support.

Taurine is a popular ingredient in sports nutrition due to its role in muscle function and recovery. The improved properties of N-cyclohexyltaurine could make it a better alternative, potentially providing athletes with better performance enhancements and faster recovery times.

References

2005. CE determination of small ions: methods and techniques. Analytical and Bioanalytical Chemistry, 384(2).
DOI: 10.1007/s00216-005-0186-3