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

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• 作者：Rodrigo da Costa Duarte^a ; Renata Ongaratto^a ; Luciana Almeida Piovesan^a ; Vâ ; nia Rodrigues de Lima^a ; Valdir Soldi^b ; Aloir Antô ; nio Merlo^c ; Marcelo G. Montes D&rsquo ; Oca^a ; ^{dqmdoca@furg.br}
• 关键词：Low-molecular-weight gelators ; Fatty amino acids ; l-Serine ; Ricinoleic acid
• 刊名：Tetrahedron Letters
• 出版年：2012
• 期刊代码：109_00404039
• 类别：ch
• 出版时间：9 May, 2012
• 卷：53
• 期：19
• 页码：2454-2460
• 文件大小：3519 K

摘要

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.