Seven kinds of
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-methylene-
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-lactones with an alkyl group at the C-4 position were synthesizedaccording to a previously described method, with yields of 28-34%. These
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-methylene-
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-lactoneshad characteristic and unique odors. All
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-methylene-
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-lactones added a roast-like odor to materials.The antimicrobial effects of
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-methylene-
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-lactones were investigated by using a paper disk diffusionmethod. The results showed the
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-methylene-
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-lactones inhibited the growth of three bacteria(
Staphylococcus aureus,
Escherichia coli, and
Pseudomonas fluorescens) and two fungi (
Saccharomyces cerevisiae and
Aspergillus niger)
. In particular,
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-methylene-
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-undecalactone and
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-methylene-
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-dodecalactone exhibited potent inhibition of the growth of these microorganisms compared to butyl
p-hydroxybenzoate as standard antibiotic. The
umu test revealed that the
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-methylene-
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-lactonessuppressed the SOS-inducing activity of three mutagens, furylfuramide, UV irradiation, and Trp-P-1, respectively. The antimicrobial effects and the suppressive effects of SOS induction by
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-methylene-
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-lactones had a tendency to intensify as the number of carbons in the side chainincreased.Keywords:
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-Methylene-
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-lactones; odor; antimicrobial activity; SOD-like activity; umu test