4-Hydroxyphenylpyruvic acid

4-Hydroxyphenylpyruvic acid
Names
	Preferred IUPAC name 3-(4-Hydroxyphenyl)-2-oxopropanoic acid
	Other names 4-Hydroxyphenylpyruvate; p-Hydroxyphenylpyruvic acid; p-Hydroxyphenylpyruvate
Identifiers
CAS Number	156-39-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:15999 ;
ChEMBL	ChEMBL607712 ;
ChemSpider	954 ;
DrugBank	DB07718 ;
ECHA InfoCard	100.005.322
IUPHAR/BPS	6629;
KEGG	C01179 ;
PubChem CID	979;
UNII	0YP1694WNQ ;
CompTox Dashboard (EPA)	DTXSID80166017 ;
	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) Key: KKADPXVIOXHVKN-UHFFFAOYSA-N ; 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;
	SMILES O=C(O)C(=O)Cc1ccc(O)cc1;
Properties
Chemical formula	C9H8O4
Molar mass	180.157 g/mol
Melting point	219-220°C
Hazards
	GHS labelling:
Pictograms
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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.^[2] Additionally, 4-HPPA can be converted to homogentisic acid which is one of the precursors to ochronotic pigment.^[3]

It is an intermediary compound in the biosynthesis of scytonemin.

References