Studies on Water-Soluble Derivatives of p-Hydroxybenzoic Acid Esters

NAKATANI Hiromi, KUSUI Sadao, FUJINAWA Shohei, JONO Kumiko, YAMANO Togo

doi:10.3358/shokueishi.11.9

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p-Hydroxybenzoic Acid Esterの水溶性誘導体に関する研究
p-Hydroxybenzoic acid ester ノスイヨウセイユウドウタイニカンスルケンキュウ 3 p-Alkoxycarbonyl phenyl phosphate ノビセイブツニタイスルサヨウトリカガクテキセイシツニツイテ
III. Antimicrobial and Physico-Chemical Properties of p-Alkoxycarbonyl Phenyl Phosphates
第3報 p-Alkoxycarbonyl Phenyl Phosphateの微生物に対する作用と理化学的性質について

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Abstract

p-Alkoxycarbonyl phenyl phosphates (ACPP) were synthesized as a water-soluble derivative of p-hydroxybenzoic acid esters, and then the antimicrobial activities of ACPP were investigated. It was found that all the ACPP were specifically effective in low concentrations against hiochi bacteria. p-Heptoxycarbonyl phenyl phosphate (PP-7), one of ACPP, was studied in detail, as ACPP seemed to be suitable for a preservative of sake. (1) Minimum inhibitory concentration (M. I. C.) of PP-7 on hiochi bacteria ranged from 12.5 to 50ppm. It was about ten times as effective as salicylic acid. (2) PP-7 was easily soluble in sake, 15% ethanol, and water. (3) PP-7 was slowly hydrolyzed to phosphoric acid and heptyl p-hydroxybenzoate (P-7) in acid media. Furthermore, P-7 had the equivalent antimicrobial activity on hiochi bacteria. (4) The acute toxicity of PP-7 was as low as P-7 (LD₅₀p. o. in mice: PP-77.6g/kg). It was lower than that of salicylic acid. From the facts described above, it may be concluded that PP-7 has the possibility of being used as the new preservative for sake and beer.

Journal

Food Hygiene and Safety Science (Shokuhin Eiseigaku Zasshi)

Food Hygiene and Safety Science (Shokuhin Eiseigaku Zasshi) 11 (1), 9-16, 1970

Japanese Society for Food Hygiene and Safety

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Studies on Water-Soluble Derivatives of <I>p</I>-Hydroxybenzoic Acid Esters