Flavor extracts of four different varieties of fresh cherry fruit were obtained using a static vacuum extraction apparatus. The extracts were analysed using GC-MS and three chiral compounds were found in all the cherry varieties: limonene, linalool, and α-terpineol. Multidimensional GC (MDGC), incorporating a cyclodextrin based stationary phase, was used to separate the enantiomers of these chiral compounds. Enantiomeric excesses of (R)-(+)-limonene, (R)-(-)-linalool and (R)-(+)-α-terpineol were found. Each variety of cherry was canned and heat processed in a retort. The canned cherries were then extracted and analysed under similar conditions to the fresh samples. The canned cherries contained the same chiral compounds as found in the fresh. However, the concentration of the chiral compounds changed slightly on processing. Limonene showed a decrease in total concentration whereas α-terpineol increased. Moreover, analysis by MDGC showed a marked decrease in the enantiomeric excess of (R)-(+)-limonene, and small decreases for (R)-(-)-linalool and (R)-(+)-α-terpineol. Chiral compounds are frequently found among the flavor volatiles of fruits and, like many naturally occurring chiral compounds, one enantiomer usually exists with a greater preponderance when compared with its antipode. Chiral odor compounds may show qualitative and quantitative differences in their odor properties (7). For example, (/£)-(+)-limonene has an orange-like aroma while («S)-(-)-limonene is turpentine-like; (£)-(+)-carvone is characteristic of caraway while its enantiomer has a spearmint odor (2). However, other chiral compounds, such as y and 6-lactones, show very little enantioselectivity of odor perception (7). The occurrence of chiral flavor compounds in enantiomeric excess provides the analyst with a means of authenticating natural flavorings, essential oils, and other plant extracts. The advent of cyclodextrin-based gas chromatography'stationary phases has resulted in considerable activity in the analysis of chiral compounds in flavor extracts of fruits, spices and other plants (3-7).