4-Hydroxyphenylpyruvic acid

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.[1] Additionally, 4-HPPA can be converted to homogentisic acid which is one of the precursors to ochronotic pigment.[2]

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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

It is an intermediary compound in the biosynthesis of scytonemin.

See also

• 4-Hydroxyphenylpyruvate dioxygenase

References

1. Brand, Larry; Harper, Alfred (1974). "Effect of glucagon on phenylalanine metabolism and phenylalanine-degrading enzymes in the rat". Biochemical Journal. 142 (2): 231–45. PMC 1168273. PMID 4155291.
2. Denoya, Claudio; Skinner, Deborah; Morgenstern, Margaret (September 1994). "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 of Bacteriology. 1 (17): 5312–5319. PMC 196716. Retrieved 18 July 2011.