MOLECULE

4-Hydroxyphenylacetaldehyde

4-Hydroxyphenylacetaldehyde, also known as POH-PH-CH2CHO, belongs to the class of organic compounds known as phenylacetaldehydes. Phenylacetaldehydes are compounds containing a phenylacetaldehyde moiety, which consists of a phenyl group substituted at the second position by an acetalydehyde. 4-Hydroxyphenylacetaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 4-Hydroxyphenylacetaldehyde has been detected, but not quantified in, several different foods, such as purple mangosteens, cottonseeds, garden cress, borages, and colorado pinyons. This could make 4-hydroxyphenylacetaldehyde a potential biomarker for the consumption of these foods. The condensation of 4-hydroxyphenylacetaldehyde and dopamine is a key step in the biosynthesis of benzylisoquinoline alkaloids. In both species, it is subsequently metabolized into 4-hydroxyphenylacetate by aldehyde dehydrogenase (ALDH) enzymes in humans and the phenylacetaldehyde dehydrogenase (feaB) enzyme in E. coli. These natural products include berberine and morphine. 4-Hydroxyphenylacetaldehyde is expected to be in Cannabis as all living plants are known to produce and metabolize it.