Abstract
Abstract(R)—(+)‐Limonene was photooxidized in the presence of Rose Bengal as catalyst. After TLC isolation, the hydroperoxides formed were separated directly by HRGC and analyzed by MS (El; Cl). Each hydroperoxide isomer was then isolated by HPLC for structure determination which after reduction of the HOO group with sodium borohydride was performed by 1H‐NMR and 13C‐NMR.Six hydroperoxide isomers formed by oxidation of the endocyclic double bond were identified. The compounds eluted from the HRGC column in the following order (proportions are given in brackets) I (40.1%) (1S, 4R)‐p‐mentha‐2, 8‐diene 1‐hydroperoxide; II (5.8%) (1R, 4R)‐p‐mentha‐2, 8‐diene 1‐hydroperoxide; III (20.6%) (2R, 4R)‐p‐mentha‐[1(7), 8]‐diene 2‐hydroperoxide; IV (8.5%) (2R, 4R)‐p‐mentha‐6, 8‐diene 2‐hydroperoxide; V (4%) (2S, 4R)‐p‐mentha‐6, 8‐diene 2‐hydroperoxide; and VI (21.0%) (2S, 4R)‐p‐mentha‐[1(7), 8]‐diene 2‐hydroperoxide. Direct HRGC separation of the limonene hydroperoxides offers, inter alia, the possibility of determining their flavor qualities by HRGC/effluent sniffing.
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