4-Hydroxyphenylpyruvic Acid

4-Hydroxyphenylpyruvic acid (4-HPPA) is an intermediate in the metabolism of aromatic amino acids, including the conditionally essential amino acid L-tyrosine (Cay-36333) and essential amino acid L-phenylalanine (Cay-31498). It is formed from L-tyrosine by tyrosine transaminase and is converted to homogentisic acid (Cay-20045) by 4-hydroxyphenylpyruvate dioxygenase. 4-HPPA inhibits LPS-induced IL-6 and nitric oxide (NO) production in RAW 264.7 macrophages (IC50s = 2 and 0.5 mM, respectively). It decreases serum starvation-induced mitochondrial superoxide production in EA.hy926 endothelial cells in vitro and increases survival in a rat model of hemorrhagic shock. Serum and urinary levels of 4-HPPA are increased in patients with alkaptonuria, an inborn error of metabolism characterized by a deficiency of 4-hydroxyphenylpyruvate dioxygenase, osteoarthropathy, and cardiac valve disease.Formal Name: 4-hydroxy-alpha-oxo-benzenepropanoic acid. CAS Number: 156-39-8. Synonyms: HPPA, 3-(4-Hydroxyphenyl)pyruvic Acid, p-4-Hydroxyphenylpyruvic Acid, para-4-Hydroxyphenylpyruvic Acid, NSC 100738, NSC 666757. Molecular Formula: C9H8O4. Formula Weight: 180.2. Purity: >95%. Formulation: (Request formulation change), A solid. Solubility: Acetonitrile: Soluble, Methanol: Soluble. SMILES: O=C(C(CC1=CC=C(C=C1)O)=O)O. InChi Code: InChI=1S/C9H8O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,10H,5H2,(H,12,13). InChi Key: KKADPXVIOXHVKN-UHFFFAOYSA-N.