Natural Abundance (2)H Nuclear Magnetic Resonance Study of the Origin of Raspberry Ketone

The site-specific natural abundance deuterium distribution of raspberry ketone 3 obtained through a variety of methods has been determined through (2)H NMR spectroscopy. This technique provided a means of distinguishing between "natural" raspberry ketones biogenerated from 4-hydroxybenzalacetone (2), obtained from 4-hydroxybenzaldehyde of extractive botanical origin and acetone produced by sugar fermentation by reduction using baker's yeast and other microorganisms, and other raspberry ketone samples obtained in different "non-natural" ways. Of natural origin is also a commercial sample obtained in an unspecified manner. A mechanistic interpretation has been proposed to explain the difference of site-specific deuterium content between the examined samples.