Document Detail


Surface active molecules: preparation and properties of long chain n-acyl-l-alpha-amino-omega-guanidine alkyl acid derivatives.
MedLine Citation:
PMID:  19467126     Owner:  NLM     Status:  In-Data-Review    
Abstract/OtherAbstract:
Synopsis A new route for the synthesis of long chain N(alpha)-acyl-l-alpha-amino-omega-guamdine alkyl acid derivatives, with cationic or amphoteric character has been established. The general formula of these compounds is shown below. A physico-chemical and antimicrobial study of these products as a function of the alkyl ester or sodium salt (R), the straight chain length of the fatty acid residue (x) and the number of carbons between the omega-guanidine and omega-carboxyl group (n) has been investigated. The water solubility, surface tension, critical micelle concentration (c.m.c.) and minimum inhibitory concentration (MIC) against Gram-positive and Gram-negative bacteria (including Pseudomonas) has been determined. Dicyclohexylcarbodiimide has been used to condense fatty acids and alpha-amino-omega-guanidine alkyl acids. In these conditions protection of the omega-guanidine group is not necessary. The main characteristic of this synthetic procedure is the use of very mild experimental conditions (temperature, pH) to form the amide linkage which leads to pure optical compounds in high yield in the absence of electrolytes. The results show that some structural modifications, particularly the protection of the carboxyl group, promote variations of the surfactant and antimicrobial properties. Only those molecules with the blocked carboxyl group (cationic molecules, where R = Me, Et or Pr) showed a good surfactant and antimicrobial activity. When the carboxyl group was unprotected (amphoteric molecules, where R = Na(+)) the resulting compounds were inactive.
Authors:
R Infante; J G Dominguez; P Erra; R Julia; M Prats
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  International journal of cosmetic science     Volume:  6     ISSN:  0142-5463     ISO Abbreviation:  Int J Cosmet Sci     Publication Date:  1984 Dec 
Date Detail:
Created Date:  2009-05-26     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  8007161     Medline TA:  Int J Cosmet Sci     Country:  England    
Other Details:
Languages:  eng     Pagination:  275-82     Citation Subset:  -    
Affiliation:
Instituto de Tecnología Química y Textil (C.S.I.C.), C/ Jorge Girona Salgado, 18-26, Barcelona-34, Spain.
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