Synthesis and homologous series gelators of fatty acyl-L-phenylalanine methyl ester

doi:10.3969/j.issn.1002-7386.2015.01.007

Abstract：Objective To synthesize a series of fatty acyl-L-phenylalanine methyl ester gelators including N-myristoyl-L-phenylalanine methyl ester (C14-L-Phe-OMe),N-palmityl-L-phenylalanine methyl ester (C16-L-Phe-OMe), N-octadecanoyl-L-phenylalanine methyl ester ( C18-L-Phe-OMe ) , and to investigate their structural characteristics and property.Methods The gelators including C14-L-Phe-OMe, C16-L-Phe-OMe and C18-L-Phe-OMe were synthesized by reaction of L-phenylalanine methyl ester with chloride including myristoyl chloride , palmityl chloride and octadecanoyl chloride.Their structures were characterized by IR ,1H-NMR and MS.The melting points, gelatinizing ability and phase transition temperature in refined soybean oil were investigated .Results The C14-L-Phe-OMe, C16-L-Phe-OMe and C18-L-Phe-OMe were successfully synthesized ,moreover,their structures were identified;the melting points of three kinds of gelatins were 61.3 ~63.1℃,72.1 ~73.0℃ and 62.3 ~64.1℃, respectively;the sequence of gelatinizing ability was C16-L-Phe-OMe >C18-L-Phe-OMe >C14-L-Phe-OMe;the enthalpy (ΔH) of three kinds of gelators in refined soybean oil was 42.58 kJ/mol,22.61 kJ/mol and 65.01 kJ/mol,respectively.Conclusion The synthesized a series of gelators including C14-L-Phe-OMe,C16-L-Phe-OMe and C18-L-Phe-OMe have better gelatinizing ability in which C 16-L-Phe-OMe has the best gelatinizing ability ,which is hopeful to be used as a controlled release drug carrier in local medication .