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and beer. The constituents of essential oil of hop have been investigated by Naya et al}~3) in 1970. They elucidated the structure of 1 10 components (humuladienone, humulol, humulene epoxide-II, humulenol-II etc. as* the sesquiterpenoids), but the constituents of neutral oil of clove have not yet been investigated in detail. Both clove and hop neutral oil contain /?-caryophyllene and humuleneas major componentsin their high-boiling fractions. Thus, it can be expected that oxidation products derived from jS-caryophyllene and humulene by the biosynthesis route mayexist in their neutral essential oil. This present paper describes an investigation of such sesquiterpenoid constituents in clove and hop neutral oils. The removal of acids and phenols from the respective essential oils gave the neutral oils. More than 86 and 106 peaks were observed in the gas chromatograms of these neutral oils (Figs. 1 and 2). As shown in Table I, the 5 compoundswere identified as sesquiterpene alcohol and related epoxy-compounds by comparisons of their GCMSwith those of authentic samples. The authentic samples were synthesized by well-established methods,4~6)

High-boiling constituents of clove oil (Eugenia caryophyllata THUNB.) and hop oil (Humulus lupulus LINN.).