Natural abundance H-2 nuclear magnetic resonance study of the origin of (Z)-3-hexenol

The origin of 11 samples of (Z)-3-hexenol was studied by SNIF-NMR measurements. The results show a possible distinction between synthetic and extractive materials and those biogenerated from linolenic acid by enzymic fragmentation at position 13 of the carbon framework of the 13-hydroperoxide obtained by the action of oxygen in the presence of lipoxygenase, followed by baker's yeast-mediated reduction of the intermediate (Z)-3-hexenal. Particularly significant to this end result are the deuterium contents at relevant positions of(Z)-3-hexenol, such as 3+4 and 1. The results suggest that one sample might be a mixture of materials of extractive origin with those obtained by biodegradation from linolenic acid.