4-Hydroxyphenylacetaldehyde Explained

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.^[1]

Synthesis

4-Hydroxyphenylacetaldehyde can be synthesized from (L-tyrosine) via a parsley tyrosine decarboxylase.^[2]

Occurrence

4-Hydroxyphenylacetaldehyde is produced from the metabolism of tyramine by monoamine oxidase (MAO) enzymes in humans and the tyramine oxidase (tynA) enzyme in Escherichia coli. 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.^{[3] [4]}

The condensation of 4-hydroxyphenylacetaldehyde and dopamine is a key step in the biosynthesis of benzylisoquinoline alkaloids. These natural products include berberine and morphine.^[5]

Notes and References

1. Web site: 4-Hydroxyphenylacetaldehyde . PubChem Compound . U.S. National Library of Medicine: National Center for Biotechnology Information . 8 August 2019 . 2019-08-03 . (4-hydroxyphenyl)acetaldehyde is an alpha-CH2-containing aldehyde and a member of phenylacetaldehydes. It has a role as a human metabolite, an Escherichia coli metabolite and a mouse metabolite..
2. Torrens-Spence. Michael P.. Gillaspy. Glenda. Zhao. Bingyu. Harich. Kim. White. Robert H.. Li. Jianyong. 2012-02-11. Biochemical evaluation of a parsley tyrosine decarboxylase results in a novel 4-hydroxyphenylacetaldehyde synthase enzyme. Biochemical and Biophysical Research Communications. en. 418. 2. 211–216. 10.1016/j.bbrc.2011.12.124. 22266321 .
3. Web site: 4-Hydroxyphenylacetaldehyde . Human Metabolome Database – Version 4.0 . University of Alberta . 8 August 2019 . 2019-07-23.
4. Elovaara H, Huusko T, Maksimow M, Elima K, Yegutkin GG, Skurnik M, Dobrindt U, Siitonen A, McPherson MJ, Salmi M, Jalkanen S . Primary Amine Oxidase of Escherichia coli Is a Metabolic Enzyme that Can Use a Human Leukocyte Molecule as a Substrate . PLOS ONE . 10 . 11 . e0142367 . 2015 . 26556595 . 4640556 . 10.1371/journal.pone.0142367 . 2015PLoSO..1042367E . free .
5. Molecular cloning and characterization of norcoclaurine synthase, an enzyme catalyzing the first committed step in benzylisoquinoline alkaloid biosynthesis. Samanani N, Liscombe DK, Facchini PJ. Plant Journal. 2004. 40. 2. 302–313. 10.1111/j.1365-313X.2004.02210.x. 15447655. free.