170501-45-8Relevant academic research and scientific papers
Synthesis and biological activity of α-methylene-γ-lactones as new aroma chemicals
Miyazawa, Mitsuo,Shimabayashi, Hiroshi,Hayashi, Shuichi,Hashimoto, Seiji,Nakamura, Sei-Ichi,Kosaka, Hiroshi,Kameoka, Hiromu
, p. 5406 - 5410 (2007/10/03)
Seven kinds of α-methylene-γ-lactones with an alkyl group at the C-4 position were synthesized according to a previously described method, with yields of 28-34%. These α-methylene-γ-lactones had characteristic and unique odors. All α-methylene-γ-lactones added a roast-like odor to materials. The antimicrobial effects of α-methylene-γ-lactones were investigated by using a paper disk diffusion method. The results showed the α-methylene-γ-lactones inhibited the growth of three bacteria (Staphylococcus aureus, Escherichia coli, and Pseudomonas fluorescens) and two fungi (Saccharomyces cerevisiae and Aspergillus niger). In particular, α-methylene-γ-undecalactone and α-methyleneγ-dodecalactone exhibited potent inhibition of the growth of these microorganisms compared to butyl p-hydroxybenzoate as standard antibiotic. The umu test revealed that the α-methylene-γ-lactones suppressed the SOS-inducing activity of three mutagens, furylfuramide, UV irradiation, and TrpP-1, respectively. The antimicrobial effects and the suppressive effects of SOS induction by α-methylene-γ-lactones had a tendency to intensify as the number of carbons in the side chain increased.
