アルキルレゾルシンの低重合ポリオキシエチレンモノエーテルの合成と抗菌性

概要

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Tetra-ethyleneglycol monoethers of butyl, pentyl, hexyl, heptyl and octyl resorcinols were prepared by the reaction of tetra-ethyleneglycol monochloride with alkyl resorcinols which had been obtained by acylation of resorcinol with fatty acid, followed by Clemmensen's reduction. The monochloride used had been produced from ethylene chlorohydrin and ethylene oxide. Surface tension of the aqueous solutions of these ethers was determined and it was found that as the number of carbon atoms in the alkyl group increased from four to eight, the surface tension lowered to about 30 dyne/cm. Antimicrobial activity of the monoethers was evaluated in terms of minimum inhibitory concentration (MIC) by agar streak method. Monoethers of butyl and pentyl resorcinols were as active as hexylresorcinol but other monoethers were more active than those although the number of OH group in the monoethers was less than that in alkylresorcinol. Of those ethers, that of heptylresorcinol gave the lowest MIC. Moreover, di-, tri- and tetra-ethylene-glycol monoethers of hexylresorcinol were prepared. The antimicrobial activity of tetra-ethyleneglycol monoether was found highest of the three.