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Synthesis of the isofatty acid 13-methyl-tetradecanoic acid and its triglyceride

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Author(s): Zlatanos, S. | Laskaridis, K. | Koliokota, E. | Sagredos, A.

Journal: Grasas y Aceites
ISSN 0017-3495

Volume: 62;
Issue: 4;
Start page: 462;
Date: 2011;
Original page

Keywords: Isofatty acid | 13-methyl-tetradecanoic acid (iso 15:0) | Isofatty acid 13- methyl-11cis-tetradecenoic acid (iso 15:1 | ω3 c) | Triglyceride of 13-methyl-tetradecanoic acid | Ácido 13-metil-tetradecanoico (15:0 iso) | Ácido graso | Iso-13-metil-11cis-tetradecenoico (15:1 iso | ω3 c) | Iso ácido graso | Triglicéridos del ácido 13-metiltetradecanoico

ABSTRACT
A new and more convenient synthesis of the isofatty acid 13-methyl-tetradecanoic acid and its triglyceride is described here. This isofatty acid is prepared through elongation of the undecanoic acid chain with isobutyraldehyde according to Wittig by the reaction between bromo-undecanoic acid ethyl ester-triphenylphosphonium salt and sodium methoxide followed by the addition of isobutyraldehyde. Its triglyceride is formed by the esterification of the free isofatty acid with glycerin without catalyst. Its purity was over 99% after high refining over activated silica gel. Total yield was estimated to be 22,8%.Una nueva y práctica síntesis del ácido graso iso-13-metil- tetradecanoico y sus triglicéridos se describe aquí. Este iso- ácido graso se prepara a través de la elongación de la cadena del ácido undecanoico con isobutiraldehido según Wittig por reacción entre la sal de bromuro de undecanoico etil-éster trifenilfosfonio y metilato sódio seguido de la adición de isobutiraldehido. Su triglicérido está formado por la esterificación del iso ácido graso libre con glicerina sin catalizador. Su pureza es superior al 99%, después de una alta refinación sobre gel de sílice activado. El rendimiento total se estimó en el 22,8%.
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