4-Hydroxyphenylacetaldehyde
Chemical compound
From Wikipedia, the free encyclopedia
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]
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| Names | |
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| Preferred IUPAC name
(4-Hydroxyphenyl)acetaldehyde | |
| Other names
p-Hydroxyphenylacetaldehyde | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.216.847 |
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| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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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 labelling: | |
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| Warning | |
| H302, H312, H315, H319, H332, H335 | |
| P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.[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]
