TITLE:
Ring Opening of Epoxy Fatty Esters by Nucleophile to Form the Derivatives of Substituted β-Amino Alcohol
AUTHORS:
Himani Varshney, Aiman Ahmad, Abdul Rauf
KEYWORDS:
Triazole; Epoxide of Ester of Fatty Acid; Ring Opening
JOURNAL NAME:
Food and Nutrition Sciences,
Vol.4 No.9A,
August
21,
2013
ABSTRACT: The nucleophilic ring opening of epoxy fatty esters was carried out using the amino-1,2,4-triazole to yield substituted derivatives of β-amino alcohol. The synthesis of the substituted beta amino alcohols has been achieved by refluxing equimolar quantities of long chain epoxy esters (epoxy fatty esters) and 4-amino-1,2,4-triazole in dichloromethane to yield following compounds, methyl 10-(4'-amino-1',2',4'-triazole)-11-hydroxy undecanoate (V), methyl 9-(4'-amino-1', 2',4'-triazole)-10-hydroxy octadecanoate (VI), methyl 9-(4'-amino-1',2',4'-triazole)-10,12-dihydroxy octadecanoate (VII), methyl 12-(4'-amino-1',2',4'-triazole)-9,13-dihydroxy octadecanoate (VIII). Epoxides of esters of fatty acids were obtained by reaction of esters of fatty acids with mchloroperbenzoic acid. All the newly synthesized compounds were characterized by IR, 1H NMR, 13C NMR and mass spectrometry.