116296-79-8Relevant academic research and scientific papers
2-(2-Butenylidene)-3,3-dimethyl-5-(2-oxopropyl)tetrahydrofuran: A New Degradation Product of 3-Hydroxy-5,6-epoxy-β-ionol
Neugebauer, Wolfgang,Winterhalter, Peter,Schreier, Peter
, p. 2885 - 2888 (2007/10/02)
Identification of 2-(2-butenylidene)-3,3-dimethyl-5-(2-oxopropyl)tetrahydrofuran diastereomers (4,5) in various leaves was achieved by comparison of HRGC retention and spectral (MS; vapor phase FTIR) data with those of synthetic references. Model experiments revealed their acid-catalyzed formation from 3-hydroxy-5,6-epoxy-β-ionol that was present in glycosidically bound form in the above mentioned leaves. Assignment of the isomers 4a/4b and 5a/5b was established by NOE experiments. Enantiodifferentiation carried out by on-line coupled multidimensional gas chromatography-mass spectrometry revealed the occurrence of enantiomerically pure 5S enantiomers 4b/5b in the natural sources. A pathway for the selective formation of 4b/5b in nature is proposed. Keywords: 2-(2-Butenylidene)-3,3-dimethyl-5-(2-oxopropyl)tetrahydrofuran; 3-hydroxy-5,6-epoxy-β-ionol; norisoprenoid degradation; multidimensional gas chromatography-mass spectrometry
A C13-norisoprenoid gentiobioside from quince fruit.
Winterhalter,Harmsen,Trani
, p. 3021 - 3025 (2007/10/02)
The beta-D-gentiobioside [beta-D-glucopyranosyl(1----6)-beta-D-glucopyranoside] of 3-hydroxy-beta-ionol has been isolated and characterized in quince (Cydonia oblonga) fruit through spectral and chemical studies. Model experiments carried out with this new natural compound revealed its important role as precursor of a number of C13-norisoprenoid flavour compounds of quince essential oil.
