4-Hydroxyphenylpyruvic acid (156-39-8)

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  1 g
  $69.00

  5 g
  $226.00

Most-cited Publications

• 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, 1994)
• A nonsense mutation in the 4-hydroxyphenylpyruvic acid dioxygenase gene (Hpd) causes skipping of the constitutive exon and hypertyrosinemia in mouse strain III (Genomics, 1995)
• Mutations in the 4-hydroxyphenylpyruvic acid dioxygenase gene are responsible for tyrosinemia type III and hawkinsinuria (Molecular Genetics and Metabolism, 2000)
• Alkaline conversion of 4-hydroxyphenylpyruvic acid to 4-hydroxybenzaldehyde. (Nature, 1960)
• Primary structure deduced from complementary DNA sequence and expression in cultured cells of mammalian 4-hydroxyphenylpyruvic acid dioxygenase : evidence that the enzyme is a homodimer of identical subunits homologous to rat liver-specific alloantigen F (Journal of Biological Chemistry, 1992)
• Conversion of 4-hydroxyphenylpyruvic acid into homogentisic acid at the thylakoid membrane of Lemna gibba. (FEBS Letters, 1979)

Areas of Application

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Trends

Alternate Names

• para-hydroxyphenylpyruvic acid
• 4-hydroxyphenylpyruvic acid, ion
• 4-hydroxyphenylpyruvate
• (p-hydroxyphenyl)pyruvic acid
• p-hydroxyphenylpyruvate
• 4-hydroxyphenylpyruvic acid, sodium salt
• SMILES
  C1=CC(=CC=C1CC(=O)C(=O)O)O
• InChIKey
  KKADPXVIOXHVKN-UHFFFAOYSA-N

External Links

• Pubchem - 4-Hydroxyphenylpyruvic acid
• Wikipedia - 3-(4-hydroxyphenyl)pyruvic acid
  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.

Synthesis

Phenol  +  3-Chloro-2-oxopropanoic acid (Friedel-Crafts alkylation)

Reactant  +  dimethyl sulfide (Corey-Kim oxidation of secondary alcohols)

Synthesis of 4-Hydroxyphenylpyruvic acid ›

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4-Hydroxyphenylpyruvic acid

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