Abstract
The challenge to develop enantioselective analytical methods to quantify chiral compounds in food and environmental matrices is an actual and imperative issue. It is well known that enantiomers may differ in their biological activities, but the stereochemistry and the discrimination of enantiomers are frequently ignored in analytical workflows. However, the knowledge about their proportion is crucial to guarantee food and environmental safety. In this sense, chiral analysis is a valuable tool to evaluate food quality and genuineness, to determine the geographical origin of a certain sample aiming to find out fraud or adulteration, to investigate toxicity and bioaccumulation of environmental contaminants (e.g., pharmaceuticals and pesticides). This chapter highlights the importance of chiral analysis in food matrices and its relationship with the environmental contamination. The last advances in chiral analysis by liquid chromatography (LC), gas chromatography (GC), and supercritical fluid chromatography (SFC) coupled to mass spectrometry (MS) are presented, with a special remark in the type of chiral column used for chromatography and the proposed workflow in the method development. Some of the most recent applications in chiral analysis of food and beverages, environmental monitoring of surface water, wastewater, soils, biodegradation studies, and contamination of foodstuff are presented and critically discussed.
Graphical Abstract

Keywords
- Chiral chromatography
- Chiral stationary phase
- Enantiomers
- Pesticides
- Pharmaceuticals
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Acknowledgments
This work was supported by national funds through the FCT/MCTES (PIDDAC) under the project PTDC/CTA-AMB/6686/2020; by UIDB/04423/2020 and UIDP/04423/2020 (Group of Natural Products and Medicinal Chemistry) and CESPU: CHIRALSINTESE-APSFCT-IINFACTS_2021.
ARR would like to acknowledge: Project POCI-01-0145-FEDER-030521 funded by ERDF funds through COMPETE2020 – POCI and by National Funds (PIDDAC) through FCT/MCTES; the scientific collaboration under Base-UIDB/50020/2020 and Programmatic-UIDP/50020/2020 Funding of LSRE-LCM, funded by national funds through FCT/MCTES (PIDDAC); and FCT funding under DL57/2016 Transitory Norm Programme.
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Ribeiro, A.R.L., Maia, A.S., Ribeiro, C., Tiritan, M.E. (2022). Chiral Analysis with Mass Spectrometry Detection in Food and Environmental Chemistry. In: Picó, Y., Campo, J. (eds) Mass Spectrometry in Food and Environmental Chemistry. The Handbook of Environmental Chemistry, vol 119. Springer, Cham. https://doi.org/10.1007/698_2022_889
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