Abstract
Ibuprofen is a nonsteroidal anti-inflammatory drug (NSAID), also known for its significant antipyretic and analgesic properties. This chiral drug is commercialized in racemic form; however, only S-(+)-ibuprofen has clinical activities. In this paper the effect of temperature change (from 288.15 to 308.15 K) on the ibuprofen resolution was studied. A column (250×4.6 mm) packed with tris(3,5-dimethylphenylcarbamate) was used to obtain the thermodynamic parameters, such as enthalpy change (ΔH), entropy change (ΔS), variation enthalpy change (ΔΔH), variation entropy change (ΔΔS), and isoenantioselective temperature (Tiso). The mobile phase was a combination of hexane (99%), isopropyl alcohol (1%), and TFA (0.1%), as an additive. The conditions led to a selectivity of 1.20 and resolution of 4.55. The first peak, R-(−)-ibuprofen, presented an enthalpy change of 7.21 kJ/mol and entropy change of 42.88 kJ/K·mol; the last peak, S-(+)-ibuprofen, has an enthalpy change of 8.76 kJ/mol and 49.40 kJ/K·mol of entropy change.
Highlights
The importance of stereochemical compound has been studied since Louis Pasteur observed the chiral phenomenon in 1848
This paper aims to study the adsorption of ibuprofen on cellulose tris(3,5-dimethylphenylcarbamate) and to evaluate the effect of temperature in chiral separation
Racemic ibuprofen can be separated using a chiral stationary phase based on cellulose tris(3,5-dimethylphenylcarbamate) and a high nonpolar mobile phase
Summary
The importance of stereochemical compound has been studied since Louis Pasteur observed the chiral phenomenon in 1848. Chiral recognition and enantiomer distinction are fundamental phenomena in nature and chemical systems. They are present in several fields, in particular bioactive compounds, drugs, pollutants, agrochemicals, food additives, and flavors. The most significant developments in chirotechnologies were spurred by demands of drug discovery in pharmaceutical industries. The liquid chromatography has been used to provide support in drug discovery, analytical methods, and advances in preparative technique of purification [1, 2]. (RS)-2-(4-(2-methylpropyl)phenyl)propanoic acid, known as ibuprofen, is one of the most widely used nonsteroidal anti-inflammatory drugs (NSAIDs) for the treatment of arthropathies. This enantiomer is a prostaglandin and thromboxane inhibitor [3].
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