Chiral Analysis of Ibuprofen using a Circular Dichroism Detector

Introduction

Ibuprofen is a well known non-steroidal anti-inflammatory drug and widely used for pain relief and fever reduction. Only the S enantiomer of ibuprofen has active antipyretic properties, but within the human body an enzymatic reaction can readily convert the R enantiomer into the S enantiomer.

The Circular Dichroism detector is well known for its high accuracy and selectivity for chiral analysis of compounds that have chromophores close to the chiral center. Both CD and UV signal are measured simultaneously and spectral scanning can be used to optimize the wavelength of interest, which is important in the measurement of chiral compounds. Not only can the CD detector help differentiate between two enantiomers, but it can also distinguish between achiral impurities and enantiomers of interest.

Experimental

Results

Fig. 1 Chromatograms of caffeine and racemic ibuprofen standards. The UV chromatogram shows that both compounds are detected, but in the CD chromatogram only ibuprofen can be detected, as the caffeine is achiral. Fig. 2 CD and UV spectra (measured using stopped-flow).