Names | |
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Preferred IUPAC name
(4-Hydroxyphenyl)acetaldehyde | |
Other names
p-Hydroxyphenylacetaldehyde
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Identifiers | |
3D model (
JSmol)
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3DMet | |
ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.216.847 |
EC Number |
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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: | |
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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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]
4-Hydroxyphenylacetaldehyde can be synthesized from ( L-tyrosine) via a parsley tyrosine decarboxylase. [2]
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]
(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.