3674-23-5Relevant academic research and scientific papers
Heterocyclic acetals from glycerol and acetaldehyde in port wines: Evolution with aging
Da Silva Ferreira, Antonio Cesar,Barbe, Jean-Christophe,Bertrand, Alain
, p. 2560 - 2564 (2007/10/03)
In Port wine, isomers of glycerol and acetaldehyde acetals have been found at total contents ranging from 9.4 to 175.3 mg/L. During oxidative aging, the concentrations of the 5-hydroxy-2-methyl-1,3-ioxane and 4-hydroxymethyl-2-methyl-1,3-dioxolane isomers increased with time showing a linear correlation (r > 0.95). The flavor threshold for the mixture of the four isomers was evaluated in wine at 100 mg/L. Thus, it is expected that they contribute to old Port wine aroma in wines older than 30 years. Experiments with model solutions and wine clearly demonstrated that SO2 combines with acetaldehyde and blocks the acetalization reaction.
NMR Spectra, MO Calculations of Spin-Spin Coupling Constants and Conformational Analysis of Substituted 1,3-Dioxolanes
Benassi, Rois,Schenetti, Luisa,Taddei, Ferdinando,Villa, Luigi,Ferri, Vincenzo
, p. 17 - 25 (2007/10/02)
The NMR spectra of a number of 2,4-disubstituted 1,3-dioxolanes have been recorded and the proton chemical shifts and coupling constants derived from complete spectral analysis.Vicinal coupling constants were found to be dependent on the substituent at C-4 and this effect is more pronounced for J(trans) of the C-4 - C-5 fragment.These coupling constants also indicate a homogeneous behaviour within a series with either a cis or trans configuration, although the cis behaviour differs from that of trans isomers.This has been interpreted in terms of definite ring conformations in substituted derivatives, while the unsubstituted 1,3-dioxolane undergoes free pesudorotation.Calculations of coupling constants were performed by semi-empirical MO methods, both for unsubstituted 1,3-dioxolane and for C-4 substituted derivatives in a large number of conformations, in order to compare calculated and experimental values; the correct order of J(cis) and J(trans) for 1,3-dioxolane is obtained only by employing energies from ab-inito MO calculations averaged over the pseudorotation circuit.For the C-4 substituted compounds calculated coupling constants were employed in a 'trial and error' process for the identification of the preferred conformations of these compounds; a set of two torsional angles for each compound was derived which allows a tentative description of the geometry of each molecule.A criticism of these geometries is given according to the evidence available on the structure of substituted 1,3-dioxolanes.
