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 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:15999 ;
ChEMBL	ChEMBL607712 ;
ChemSpider	954 ;
DrugBank	DB07718 ;
ECHA InfoCard	100.005.322
IUPHAR/BPS	6629;
KEGG	C01179 ;
PubChem CID	979;
UNII	0YP1694WNQ ;
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) Key: KKADPXVIOXHVKN-UHFFFAOYSA-N ; 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
Hazards
	GHS labelling:
Pictograms
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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.

References

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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^[1]
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