4-Hydroxyphenylpyruvic acid
Appearance
(Redirected from Para-Hydroxyphenylpyruvate)
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Names | |
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Preferred IUPAC name
3-(4-Hydroxyphenyl)-2-oxopropanoic acid | |
Other names
4-Hydroxyphenylpyruvate
p-Hydroxyphenylpyruvic acid p-Hydroxyphenylpyruvate | |
Identifiers | |
3D model (JSmol)
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ChEBI | |
ChEMBL | |
ChemSpider | |
DrugBank | |
ECHA InfoCard | 100.005.322 |
KEGG | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C9H8O4 | |
Molar mass | 180.157 g/mol |
Melting point | 219-220°C[1] |
Hazards | |
GHS labelling: | |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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
[edit]References
[edit]- ^ a b https://pubchem.ncbi.nlm.nih.gov/compound/979
- ^ 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.