4-Hydroxyphenylpyruvic acid

4-Hydroxyphenylpyruvic acid
IUPAC name
3-(4-hydroxyphenyl)-2-oxo-propanoic acid
Other names
p-Hydroxyphenylpyruvic acid
156-39-8 N
3D model (Jmol) Interactive image
ChEBI CHEBI:15999 YesY
ChEMBL ChEMBL607712 YesY
ChemSpider 954 YesY
DrugBank DB07718 YesY
ECHA InfoCard 100.005.322
KEGG C01179 YesY
PubChem 979
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

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]

It is an intermediary compound in the biosynthesis of scytonemin.

See also


  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 1168273Freely accessible. 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. Retrieved 18 July 2011.

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