4-Hydroxyphenylacetaldehyde

4-Hydroxyphenylacetaldehyde, also known as p-hydroxyphenylacetaldehyde, is a natural product with the formula HOC₆H₄CH₂CHO.
It is a derivative of phenylacetaldehyde and occurs as a white solid at room temperature.

Synthesis

4-Hydroxyphenylacetaldehyde can be synthesized from via a parsley tyrosine decarboxylase.

Occurrence

4-Hydroxyphenylacetaldehyde is produced from the metabolism of tyramine by monoamine oxidase enzymes in humans and the tyramine oxidase enzyme in Escherichia coli. In both species, it is subsequently metabolized into 4-hydroxyphenylacetate by aldehyde dehydrogenase enzymes in humans and the phenylacetaldehyde dehydrogenase enzyme in E. coli.
The condensation of 4-hydroxyphenylacetaldehyde and dopamine is a key step in the biosynthesis of benzylisoquinoline alkaloids. These natural products include berberine and morphine.