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Home / Applications / Chiral Analysis of Ibuprofen using a Circular Dichroism Detector

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Chiral Analysis of Ibuprofen using a Circular Dichroism Detector

By Miyuki Kanno

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October 9, 2024

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

Keywords

101016H

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).

 

This document has been prepared based on information available at the time of publication and is subject to revision without notice. Although the contents are checked with the utmost care, we do not guarantee their accuracy or completeness. JASCO Corporation assumes no responsibility or liability for any loss or damage incurred as a result of the use of any information contained in this document. Copyright and other intellectual property rights in this document remain the property of JASCO Corporation. Please do not attempt to copy, modify, redistribute, or sell etc. in whole or in part without prior written permission.

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About the Author

Miyuki Kanno

JASCO Application Note

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).

 

Keywords

101016H

This document has been prepared based on information available at the time of publication and is subject to revision without notice. Although the contents are checked with the utmost care, we do not guarantee their accuracy or completeness. JASCO Corporation assumes no responsibility or liability for any loss or damage incurred as a result of the use of any information contained in this document. Copyright and other intellectual property rights in this document remain the property of JASCO Corporation. Please do not attempt to copy, modify, redistribute, or sell etc. in whole or in part without prior written permission.
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