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 |
|
3D model (JSmol) |
|
ChEBI |
|
ChEMBL |
|
ChemSpider |
|
DrugBank |
|
ECHA InfoCard | 100.005.322 ![]() |
IUPHAR/BPS |
|
KEGG |
|
PubChem CID |
|
UNII |
|
CompTox Dashboard (EPA) |
|
InChI
| |
| |
Properties | |
Chemical formula | C9H8O4 |
Molar mass | 180.157 g/mol |
Melting point | 219-220°C[1] |
Hazards | |
GHS labelling: | |
Pictograms | ![]() |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). ![]() ![]() ![]() Infobox references |
Chemical compound
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
References
- ^ a b "4-Hydroxyphenylpyruvic acid".
- ^ 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.
- ^ 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.
- v
- t
- e