4-Hydroxyphenylacetaldehyde

4-Hydroxyphenylacetaldehyde
Names
	IUPAC name 2-(4-Hydroxyphenyl)acetaldehyde
	Other names p-Hydroxyphenylacetaldehyde
Identifiers
CAS Number	7339-87-9;
3D model (JSmol)	Interactive image;
3DMet	B00637;
ChEBI	CHEBI:15621;
ChemSpider	389113;
ECHA InfoCard	100.216.847
EC Number	689-849-1;
KEGG	C03765;
PubChem CID	440113;
CompTox Dashboard (EPA)	DTXSID00223631;
	InChI InChI=1S/C8H8O2/c9-6-5-7-1-3-8(10)4-2-7/h1-4,6,10H,5H2 Key: IPRPPFIAVHPVJH-UHFFFAOYSA-N;
	SMILES C1=CC(=CC=C1CC=O)O;
Properties
Chemical formula	C8H8O2
Molar mass	136.150 g·mol−1
Appearance	White solid
Melting point	118 °C (244 °F; 391 K)
Hazards
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	H302, H312, H315, H319, H332, H335
GHS precautionary statements	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]

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.[2][3] 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.[2][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]

References

"4-Hydroxyphenylacetaldehyde". PubChem Compound. U.S. National Library of Medicine: National Center for Biotechnology Information. 3 August 2019. Retrieved 8 August 2019. (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.
"4-Hydroxyphenylacetaldehyde". Human Metabolome Database – Version 4.0. University of Alberta. 23 July 2019. Retrieved 8 August 2019.
Elovaara H, Huusko T, Maksimow M, Elima K, Yegutkin GG, Skurnik M, Dobrindt U, Siitonen A, McPherson MJ, Salmi M, Jalkanen S (2015). "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. Bibcode:2015PLoSO..1042367E. doi:10.1371/journal.pone.0142367. PMC 4640556. PMID 26556595.
Universal protein resource accession number P80668 at UniProt.
Samanani N, Liscombe DK, Facchini PJ (2004). "Molecular cloning and characterization of norcoclaurine synthase, an enzyme catalyzing the first committed step in benzylisoquinoline alkaloid biosynthesis". Plant Journal. 40 (2): 302–313. doi:10.1111/j.1365-313X.2004.02210.x. PMID 15447655.

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[PubChem_entry-1] "4-Hydroxyphenylacetaldehyde". PubChem Compound. U.S. National Library of Medicine: National Center for Biotechnology Information. 3 August 2019. Retrieved 8 August 2019. (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.

[HMDB_entry-2] "4-Hydroxyphenylacetaldehyde". Human Metabolome Database – Version 4.0. University of Alberta. 23 July 2019. Retrieved 8 August 2019.

[pmid26556595-3] Elovaara H, Huusko T, Maksimow M, Elima K, Yegutkin GG, Skurnik M, Dobrindt U, Siitonen A, McPherson MJ, Salmi M, Jalkanen S (2015). "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. Bibcode:2015PLoSO..1042367E. doi:10.1371/journal.pone.0142367. PMC 4640556. PMID 26556595.

[4] Universal protein resource accession number P80668 at UniProt.

[5] Samanani N, Liscombe DK, Facchini PJ (2004). "Molecular cloning and characterization of norcoclaurine synthase, an enzyme catalyzing the first committed step in benzylisoquinoline alkaloid biosynthesis". Plant Journal. 40 (2): 302–313. doi:10.1111/j.1365-313X.2004.02210.x. PMID 15447655.