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Updated: Aug 16, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Synthesis and biological activity of alpha-methylene-gamma-lactones as new aroma chemicals
M Miyazawa1, H Shimabayashi, S Hayashi
1Department of Applied Chemistry, Faculty of Science and Engineering, Kinki University, Kowakae, Higashiosaka-shi, Osaka 577-8502, Japan. miyazawa@apch.kindai.ac.jp
Abstract:
Seven kinds of alpha-methylene-gamma-lactones with an alkyl group at the C-4 position were synthesized according to a previously described method, with yields of 28-34%. These alpha-methylene-gamma-lactones had characteristic and unique odors. All alpha-methylene-gamma-lactones added a roast-like odor to materials. The antimicrobial effects of alpha-methylene-gamma-lactones were investigated by using a paper disk diffusion method. The results showed the alpha-methylene-gamma-lactones inhibited the growth of three bacteria (Staphylococcus aureus, Escherichia coli, and Pseudomonas fluorescens) and two fungi (Saccharomyces cerevisiae and Aspergillus niger). In particular, alpha-methylene-gamma-undecalactone and alpha-methylene-gamma-dodecalactone exhibited potent inhibition of the growth of these microorganisms compared to butyl p-hydroxybenzoate as standard antibiotic. The umu test revealed that the alpha-methylene-gamma-lactones suppressed 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 alpha-methylene-gamma-lactones had a tendency to intensify as the number of carbons in the side chain increased.
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