The structure of the mustard oil glucosides and synthesis of the glucotropaeolate ion
Lundeen, Allan Jay
Doctor of Philosophy
Since the first isolation of allyl isothiocyanate from the seeds of black mustard over a century ago, the occurrence of isothiocyanates in nature has frequently been reported. Organic isothiocyanates are commonly called mustard oils because of their long recognized distribution in plants of the mustard family, Cruciferae, which derived the name originally from the French condiment moustarde. Various of the mustards have been important items of commerce since ancient times. Mustard oils may be conveniently grouped as volatile and non-volatile. Volatile oils, such as allyl mustard oil, have a characteristically sharp taste and odor, whereas the non-volatile, such as p-hydroxybenzyl isothiocyanate (the active principle of table mustard), are odorless but also possess a sharp taste. Volatile mustard oils may be easily separated from the seed mixture by steam distillation, and consequently have been more extensively investigated than non-volatile mustard oils. The purpose of this investigation is to elucidate the chemical nature of the precursors of mustard oils in plants, the mustard oil glucosides.