p-Heptoxycarbonyl Phenyl Phosphate(PP-7)の清酒用保存料への利用について

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p-Alkoxycarbonyl phenyl phosphates(ACPP)were synthesized as water-soluble derivatives of p-hydroxybenzoic acid esters, and then the antimicrobial activities of ACPP were investigated. It was found that all the ACPP were specifically effective at low concentrations agains hiochi bacteria. p-Heptoxycarbonyl phenyl phosphate(PP-7), which is one of ACPP, was studied in detail, as ACPP, was studied in detail, as ACPP seemed to be suitable for preservation of sake.1) The minimum inhibitory concentration(M. I. C.) of PP-7 against hiochi bacteria ranged from 12.5 to 50 ppm. It was about 10 times as effective as salicylic acid.2) The antimicrobial activity of PP-7 was slightly affected by the subculture age, the inoculum size of hiochi bacteria and the pH or the alcohol concentration of the medium, but it was not affected the additions of peptone and sedimentation agents.3) The antimicrobial action of PP-7 against hiochi bacteria in sake was bacteriostatic, similar to that of salicylic acid.4) PP-7 was easily soluble in the sake, 15% ethanol and water.5) PP-7 was stable in the crystalline form, but it was slowly hydrolyzed to phosphoric acid and heptyl p-hydroxybenzoate(P-7)in both acid media and sake. Furthermore, the antimicrobial activity of P-7 against hiochi bacteria was equivalent that of to PP-7. 6) The acute toxicity of PP-7(LD_<50> p. o. in mice : 7.6 g/kg, in rats : 7.0 g/kg)was as low as that of P-7. It was lower than that of salicylic acid.7) PP-7 was easily hydrolyzed by phosphatase and esterase in raw sake. These enzymes were completely inactivated by pasteurization above 60℃ for 10 minutes. Then PP-7 must be added to pasteurized sake to prevent its decomposition with the enzymes.8) In sensory tests, PP-7 was found to have no influence on the qualities of sake at concentrations ranging from 25 to 35 ppm.From the facts described above, it is concluded that PP-7 seems to be a new and good preservative for sake. It is most desirable that PP-7 is added to sake within the range from 25 to 35 ppm.
公益社団法人日本生物工学会の論文
1970-04-25

p-Heptoxycarbonyl Phenyl Phosphate(PP-7)の清酒用保存料への利用について

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