4-Hydroxyphenylpyruvic acid

4-Hydroxyphenylpyruvic acid
IUPAC name 3-(4-hydroxyphenyl)-2-oxo-propanoic acid
Other names 4-Hydroxyphenylpyruvate p-Hydroxyphenylpyruvic acid p-Hydroxyphenylpyruvate
Identifiers
CAS number	156-39-8
PubChem	979
ChemSpider	954 Y
DrugBank	DB07718
KEGG	C01179 Y
ChEBI	CHEBI:15999 Y
ChEMBL	CHEMBL607712 Y
Jmol-3D images	Image 1
SMILES O=C(O)C(=O)Cc1ccc(O)cc1
InChI InChI=1S/C9H8O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,10H,5H2,(H,12,13) Y Key: KKADPXVIOXHVKN-UHFFFAOYSA-N Y InChI=1/C9H8O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,10H,5H2,(H,12,13) Key: KKADPXVIOXHVKN-UHFFFAOYAH
Properties
Molecular formula	C9H8O4
Molar mass	180.157 g/mol
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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. Additionally, 4-HPPA can be converted to homogentisic acid which is one of the precursors to ochronotic pigment.

It is an intermediary compound in the biosynthesis of scytonemin.

See also

• 4-Hydroxyphenylpyruvate dioxygenase