Synthesis and Physicochemical and Antimicrobial Properties of N, N-Bis(2-hydroxyethyl)alkylamine Oxides and Some Related Compounds

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  • KANETANI Fujio
    Department of Applied Chemistry, Faculty of Engineering, Hiroshima University
  • NEGORO Kenji
    Department of Applied Chemistry, Faculty of Engineering, Hiroshima University
  • TAKAISHI Hideo
    Department of Applied Chemistry, Faculty of Engineering, Hiroshima University

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Other Title
  • N,N-ビス(2-ヒドロキシエチル)アルキルアミンオキシドと二,三の関連化合物の合成と物理化学的性質および抗微生物性
  • Ｎ，Ｎ‐ビス（２‐ヒドロキシエチル）アルキルアミンオキシドと二，三の関連化合物の合成と物理化学的性質および抗微生物性

Description

N, N-Bis(2-hydroxyethyl)alkyiamine oxides [1] (alkyl=n-C8H17, n-C10H21, n-C12H25, n-C14H29 and n-C12H33), N, N-dimethyldodecylamine oxide [2](abbreviated as C12Me2-AO in the text), and dodecylbis(2-hydroxyethyl)methylammonium bromide [3](abbreviated as C12⋅(HOE)2Me-ABr) were prepared (Table 3). Amine oxides [1] were hygroscopic, though not so much as [2], low melting, and weak bases having pKa values of 2.75-4.50 (Table 4).<BR>Studies on the surface active properties in aqueous solution revealed that N, N-bis(2-hydroxyethyl)dodecylamine and -tetradecylamine oxides (abbreviated as C, 2-AO and CL, -AO, respectively)are good nonionic surfactants having CMC values of 4.0×10-4 and 1.0×10-3mol/l, respectively, and lower the surface tension down to ca.30 dynkm at the CMCs (Fig.2 and Table 5).<BR>Compounds [1], [2] and [3] were also tested for the antimicrobial activity against a gram-positive bacterium, Staphylococcus aureus, a gram-negative bacterium, Escherichia coli, and a fungus, Aspergillus oryzae. The results showed that amine oxides (2) have little effect on Escherichia coli and Staphylococcus aureus (Table 7), whereas C14-AO and quaternary ammonium salt [3] possess antifungal activity as high as pentachlorophenol (Table 8).

Journal

  • NIPPON KAGAKU KAISHI

    NIPPON KAGAKU KAISHI 1982 (9), 1538-1545, 1982-09-10

    The Chemical Society of Japan

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