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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.005.322 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C9H8O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,10H,5H2,(H,12,13) checkY
    Key: KKADPXVIOXHVKN-UHFFFAOYSA-N checkY
  • 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
  • O=C(O)C(=O)Cc1ccc(O)cc1
Properties
C9H8O4
Molar mass 180.157 g/mol
Melting point 219-220°C[1]
Hazards
GHS labelling:
GHS07: Exclamation mark[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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.

  1. ^ a b "4-Hydroxyphenylpyruvic acid".
  2. ^ Brand, Larry; Harper, Alfred (1974). "Effect of glucagon on phenylalanine metabolism and phenylalanine-degrading enzymes in the rat". Biochemical Journal. 142 (2): 231–45. doi:10.1042/bj1420231. PMC 1168273. PMID 4155291.
  3. ^ 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. doi:10.1128/jb.176.17.5312-5319.1994. PMC 196716. PMID 8071207.