4-Hydroxyphenylpyruvic acid

{{chembox

| Verifiedfields = changed

| verifiedrevid = 477222367

| ImageFile = 4-hydroxyphenylpyruvic acid.svg

| ImageSize =

| PIN = 3-(4-Hydroxyphenyl)-2-oxopropanoic acid

| OtherNames = 4-Hydroxyphenylpyruvate
p-Hydroxyphenylpyruvic acid
p-Hydroxyphenylpyruvate

|Section1={{Chembox Identifiers

| IUPHAR_ligand = 6629

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = C01179

| InChI = 1/C9H8O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,10H,5H2,(H,12,13)

| InChIKey = KKADPXVIOXHVKN-UHFFFAOYAH

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 607712

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C9H8O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,10H,5H2,(H,12,13)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = KKADPXVIOXHVKN-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo=156-39-8

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 0YP1694WNQ

| PubChem=979

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 15999

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB07718

| SMILES = O=C(O)C(=O)Cc1ccc(O)cc1

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 954

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|Section2={{Chembox Properties

| Formula = C₉H₈O₄

| MolarMass = 180.157 g/mol

| MeltingPtC = 219–220

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|Section3={{Chembox Hazards

| GHSPictograms = {{GHS07}}{{cite web | url=https://pubchem.ncbi.nlm.nih.gov/compound/979 | title=4-Hydroxyphenylpyruvic acid }}

}}

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4-Hydroxyphenylpyruvic acid (4-HPPA) is an intermediate in the metabolism of the amino acid phenylalanine. The aromatic side chain of phenylalanine is hydroxylated by the enzyme phenylalanine hydroxylase to form tyrosine. The conversion from tyrosine to 4-HPPA is in turn catalyzed by tyrosine aminotransferase.{{cite journal|last=Brand|first=Larry|author2=Harper, Alfred|journal=Biochemical Journal|year=1974|volume=142|pages=231–45|pmc=1168273|title=Effect of glucagon on phenylalanine metabolism and phenylalanine-degrading enzymes in the rat|issue=2|doi=10.1042/bj1420231 |pmid=4155291}} Additionally, 4-HPPA can be converted to homogentisic acid which is one of the precursors to ochronotic pigment.{{cite journal|last=Denoya|first=Claudio|author2=Skinner, Deborah|author3= Morgenstern, Margaret|title=A Streptomyces avermitilis gene encoding a 4-hydroxyphenylpyruvic acid dioxygenase-like protein that directs the production of homogentisic acid and an ochronotic pigment in Escherichia coli|journal=Journal of Bacteriology|date=September 1994|volume=1|issue=17|pages=5312–5319|doi=10.1128/jb.176.17.5312-5319.1994 |pmid=8071207 |url= |pmc=196716}}

It is an intermediary compound in the biosynthesis of scytonemin.