New N-acylamino acids and derivatives from renewable fatty acids: gelation of hydrocarbons and thermal properties

• Autor(a) principal: Duarte, Rodrigo da Costa
• Data de Publicação: 2012
• Outros Autores: Ongaratto, Renata, Piovesan, Luciana Almeida, Lima, Vania Rodrigues de, Soldi, Valdir, Merlo, Aloir Antonio, D'Oca, Marcelo Gonçalves Montes
• Tipo de documento: Artigo
• Idioma: eng
• Título da fonte: Repositório Institucional da FURG (RI FURG)
• Texto Completo: http://repositorio.furg.br/handle/1/4667; http://dx.doi.org/10.1016/j.tetlet.2012.03.015
• topic: Low-molecular-weight gelators; Fatty amino acids; L-Serine; Ricinoleic acid

This work reports the synthesis of new fatty N-acylamino acids and N-acylamino esters from the C16:0, C18:0, C18:1, and C18:1(OH) fatty acid families and demonstrates the activity of these compounds as organogel agents. Compounds were heated and dissolved in various solvents (n-hexane, toluene, and gasoline). Only saturated C16:0 and C18:0 derived from alanine were able to form gels in toluene, and saturated C16:0 derived from phenylalanine showed gelation in n-hexane. This is the first evidence that fatty N-acylamino esters and N-acylamino acid derivatives of L-serine and fatty acids C16:0, C18:0, and C18:1 are able to form gels with hexane. This observation confirms the importance of the hydroxyl group in the segment derivative of L-serine in forming good gels.