Chemistry:4-Hydroxyphenylacetaldehyde
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| Preferred IUPAC name
(4-Hydroxyphenyl)acetaldehyde | |
| Other names
p-Hydroxyphenylacetaldehyde
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| Properties | |
| C8H8O2 | |
| Molar mass | 136.150 g·mol−1 |
| Appearance | White solid |
| Melting point | 118 °C (244 °F; 391 K) |
| Hazards | |
| GHS pictograms | 
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| GHS Signal word | Warning |
| H302, H312, H315, H319, H332, H335 | |
| P261, P264, P270, P271, P280, P301+312, P302+352, P304+312, P304+340, P305+351+338, P312, P321, P322, P330, P332+313, P337+313, P362, P363, P403+233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
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 a parsley tyrosine decarboxylase (L-tyrosine).[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.[3][4] 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][5]
The condensation of 4-hydroxyphenylacetaldehyde and dopamine is a key step in the biosynthesis of benzylisoquinoline alkaloids. These natural products include berberine and morphine.[6]
References
- ↑ "4-Hydroxyphenylacetaldehyde". U.S. National Library of Medicine: National Center for Biotechnology Information. 2019-08-03. https://pubchem.ncbi.nlm.nih.gov/compound/440113. "(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."
- ↑ 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" (in en). Biochemical and Biophysical Research Communications 418 (2): 211–216. doi:10.1016/j.bbrc.2011.12.124. PMID 22266321. https://linkinghub.elsevier.com/retrieve/pii/S0006291X11023333.
- ↑ 3.0 3.1 "4-Hydroxyphenylacetaldehyde". University of Alberta. 2019-07-23. http://www.hmdb.ca/metabolites/HMDB0003767.
- ↑ 4.0 4.1 "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. doi:10.1371/journal.pone.0142367. PMID 26556595. Bibcode: 2015PLoSO..1042367E.
- ↑ Universal protein resource accession number P80668 at UniProt.
- ↑ "Molecular cloning and characterization of norcoclaurine synthase, an enzyme catalyzing the first committed step in benzylisoquinoline alkaloid biosynthesis". Plant Journal 40 (2): 302–313. 2004. doi:10.1111/j.1365-313X.2004.02210.x. PMID 15447655.
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