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2‐formylmethyl‐2‐methyl‐5‐(1‐hydroxy‐1‐methylethyl)‐tetrahydrofuran: Major volatile product of the water‐mediated oxidative decomposition of citral
Author(s) -
Grein B.,
Schmidt G.,
Full G.,
Winterhalter P.,
Schreier P.
Publication year - 1994
Publication title -
flavour and fragrance journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.393
H-Index - 70
eISSN - 1099-1026
pISSN - 0882-5734
DOI - 10.1002/ffj.2730090302
Subject(s) - chemistry , tetrahydrofuran , diastereomer , citral , chromatography , decomposition , fraction (chemistry) , gas chromatography , solvent , organic chemistry , aroma , food science , essential oil
Water‐mediated (pH 3) model experiments were performed with citral (neral/geranial 1a/1b ) under oxygen atmosphere. After complete decomposition of 1a/1b 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‐(1‐hydroxy‐1‐methylethyl)‐tetrahydrofuran diastereomers 3a/3b 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 3a/3b and their analytical stereo‐differentiation was achieved by synthesis and chromatography of the (2 R ) configured diastereomers, starting from ( R ) (—)‐linalol.