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  Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:15999  Y
ChEMBL	ChEMBL607712  Y
ChemSpider	954  Y
DrugBank	DB07718  Y
ECHA InfoCard	100.005.322
IUPHAR/BPS	6629
KEGG	C01179  Y
PubChem CID	979
UNII	0YP1694WNQ  Y
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) 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
SMILES O=C(O)C(=O)Cc1ccc(O)cc1
Properties
Chemical formula	C9H8O4
Molar mass	180.157 g/mol
Melting point	219–220 °C (426–428 °F; 492–493 K)
Hazards
GHS labelling:
Pictograms	[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  YN ?) 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.

See also

• 4-Hydroxyphenylpyruvate dioxygenase

References

1. "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.