Water-mediated (pH 3) model experiments were performed with citral (nerallgeranial la/lb) under oxygen atmosphere. After complete decomposition of l d l b and solvent extraction of the products formed, separation into neutral and acid fraction was carried out by bicarbonate treatment. Subsequent HRGC, HRGC-MS, and HRGC-FTIR analyses revealed the Occurrence of more than twenty compounds, among them geranic acid in the acid fraction and the 2-formylmethyl-2-methyl-5-( I-hydroxy-1-methylethyl)-tetrahydrofuran diastereomers 3d3b in the neutral fraction were the major products comprising approximately 15% and 80%, respectively, of the total volatiles formed. The determination of the absolute configuration of 3d3b and their analytical stereodifferentiation was achieved by synthesis and chromatography of the (2R) configured diastereomers, starting from ( R ) (-)-linalol.KEY WORDS Citral Citral decomposition 2-Formylmethyl-2-methyl-5-( 1-hydroxy-1-methylethyl)-tetrahydrofuran 2,8DMP-P-cyclodextrin
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