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Surface activities, biodegradability and antimicrobial properties of glucosamine derivatives containing alkyl chains
Author(s) -
Matsumura Shuichi,
Kawamura Yasushi,
Yoshikawa Sadao,
Kawada Kazuo,
Uchibori Tsuyoshi
Publication year - 1993
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02545361
Subject(s) - alkyl , chemistry , critical micelle concentration , amide , glucosamine , organic chemistry , anomer , antimicrobial , phenol , micelle , aqueous solution
Three series of D‐glucosamine derivatives containing an alkyl chain with 8 to 14 atoms, methyl 2‐acylamino‐2‐deoxy‐D‐glucopyranosides, n ‐alkyl 2‐acetylamino‐2‐deoxy‐D‐glucopyranosides and n ‐alkyl 2‐amino‐2‐deoxy‐D‐glucopyranoside hydrochlorides, were synthesized, and their surface properties (such as surface tension, critical micelle concentration (CMC), dynamic surface tension and foaming properties), biodegradability and antimicrobial activities were evaluated. n ‐Alkyl 2‐amino‐2‐deoxy‐D‐glucopyranoside hydrochlorides containing C8 to C12 carbon chains showed surface activities, a CMC and excellent foaming properties. The α‐anomers showed a slightly lower CMC than the β‐anomers, indicating less hydrophilicity of the α‐anomers. On the other hand, glucosamine derivatives containing amide groups showed poor surface activities in water due to their lower solubilities in water. All glucosamine derivatives containing alkyl chains were biodegraded as well as conventional ethoxylated nonionics by activated sludge from the municipal sewage treatment plant. Methyl 2‐acylamino‐2‐deoxy‐D‐glucopyranosides and n ‐alkyl 2‐amino‐2‐deoxy‐D‐glucopyranoside hydrochlorides showed a broader spectrum of antimicrobial activity than the corresponding n ‐alkyl glucopyranosides. Among them the C12 derivatives showed the best results.