Synthesis of (S)-(+)-enantiomers of food-relevant (n-5)-monoenoic and saturated anteiso-fatty acids by a Wittig reaction |
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Authors: | Saskia Thurnhofer |
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Institution: | Institute of Food Chemistry, University of Hohenheim, Garbenstr. 28, D-70599 Stuttgart, Germany |
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Abstract: | We developed an enantioselective synthesis for the food-relevant anteiso-fatty acids a15:0, a16:0, and a17:0. Different (carboxyalkyl)triphenylphosphonium bromide salts were coupled with (S)-3-methylpentanal in a Wittig reaction. Mixtures of the obtained cis-/trans-isomers were separated by Ag+-HPLC to give the novel cis-isomers of (S)-(+)-a15:1n-5, (S)-(+)-a16:1n-5, and (S)-(+)-a17:1n-5. Hydrogenation of the monoenoic products led to (S)-(+)-a15:0, (S)-(+)-a16:0, and (S)-(+)-a17:0, which are essential for the assessment of the bioactivity of tests with standards of anteiso-fatty acids. |
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Keywords: | Methyl branched fatty acids Anteiso-fatty acids Monoenoic anteiso-fatty acids Wittig reaction Enantioselective synthesis Silver-ion chromatography |
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