An intermediate in aromatic amino acid metabolism
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4-Hydroxyphenylpyruvic Acid

Item No. 38508

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-hydroxy-α-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(Learn about Variance in Solubility)
Acetonitrile: SolubleMethanol: 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
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    500 mg

    $87

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    Cayman Chemical
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    Product Description

    4-Hydroxyphenylpyruvic acid (4-HPPA) is an intermediate in the metabolism of aromatic amino acids, including the conditionally essential amino acid L-tyrosine (Item No. 36333) and essential amino acid L-phenylalanine (Item No. 31498).1,2 It is formed from L-tyrosine by tyrosine transaminase and is converted to homogentisic acid (Item No. 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).3 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.1 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.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Cotoia, A., Scrima, R., Gefter, J.V., et al. p-Hydroxyphenylpyruvate, an intermediate of the Phe/Tyr catabolism, improves mitochondrial oxidative metabolism under stressing conditions and prolongs survival in rats subjected to profound hemorrhagic shock. PLoS One 9(3), e90917 (2014).

    2. Norman, B.P., Davison, A.S., Hickton, B., et al. Comprehensive biotransformation analysis of phenylalanine-tyrosine metabolism reveals alternative routes of metabolite clearance in nitisinone-treated alkaptonuria. Metabolites 12(10), 927 (2022).

    3. Scrima, R., Menga, M., Pacelli, C., et al. Para-hydroxyphenylpyruvate inhibits the pro-inflammatory stimulation of macrophage preventing LPS-mediated nitro-oxidative unbalance and immunometabolic shift. PLoS One 12(11), e0188683 (2017).