Occurrence of the Plant Growth Regulator Chlormequat in Food May Be Due to Natural Formation: A Preliminary Mechanistic Study.

The study reports the role of choline and compounds thereof in the formation of chlormequat under thermal conditions, with emphasis on the molecular mechanism involved in the transformation. The data show the decomposition of choline to chlormequat at 200 °C in presence of chloride ions, likely by nucleophilic substitution. Furthermore, the results suggest that phosphatidylcholine, glycerophosphocholine, and phosphocholine are the effective precursors of chlormequat under sufficient thermal conditions due to their capability to degrade to choline and/or the ability of the phosphate moiety to behave as a good leaving group with respect to nucleophilic attacks. Thermal treatments (120 and 200 °C) applied to egg powder, rich in phosphatidylcholine, and wheat flour, with choline at a substantial level, suggest that less energy is required for obtaining chlormequat from phosphatidylcholine than from choline. This observation is consistent with the postulated mechanism of a nucleophilic substitution with phosphate moieties acting as better leaving groups than the hydroxyl group.