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4-Hydroxyphenylpyruvic acid

Catalog No.
M1088
An organic compound used to study the metabolic pathways of phenylpyruvic acid derivatives.
Grouped product items
SizePriceStock Qty
250mg
$50.00
In stock
500mg
$85.00
In stock
For scientific research use only and should not be used for diagnostic or medical purposes.

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Background

4-Hydroxyphenylpyruvic acid (CAS No.: 156-39-8) is an endogenous phenylpyruvic acid derivative that functions as a key metabolic intermediate in the catabolism of aromatic amino acids, particularly L-tyrosine and L-phenylalanine, and serves as a direct substrate of 4-hydroxyphenylpyruvate dioxygenase in the biosynthetic conversion to homogentisic acid. As part of this pathway, it plays an important role in cellular metabolic homeostasis and is widely utilized in biochemical and pharmacological studies investigating disorders of tyrosine metabolism, including type III tyrosinemia, hawkinsinuria, and alkaptonuria, where altered levels of this metabolite are observed. Mechanistically, 4-hydroxyphenylpyruvic acid has been reported to modulate inflammatory and oxidative stress responses, including inhibition of lipopolysaccharide-induced interleukin-6 and nitric oxide production in macrophage models and reduction of mitochondrial superoxide generation in endothelial cells, with activity observed in the low millimolar range. In addition, it has demonstrated protective effects in preclinical models of physiological stress, such as improved survival in hemorrhagic shock models, suggesting broader relevance to redox biology and cellular stress signaling pathways. This compound is commonly applied in in vitro cell-based assays and in vivo metabolic or disease models to probe enzyme function, pathway flux, and metabolic dysregulation, with experimental concentrations or dosing regimens tailored to specific study designs in drug discovery and translational research contexts.

Chemical Properties

Physical AppearanceA solid
Storage-20°C
M.Wt180.16
Cas No.156-39-8
FormulaC9H8O4
SynonymsHPPA; 3-(4-Hydroxyphenyl)pyruvic Acid; p -4-Hydroxyphenylpyruvic Acid; para -4-Hydroxyphenylpyruvic Acid; NSC 100738; NSC 666757
Solubilityinsoluble in H2O; ≥27.35 mg/mL in EtOH; ≥55.2 mg/mL in DMSO
Chemical Name3-(4-hydroxyphenyl)-2-oxopropanoic acid
Canonical SMILESOC(CCC1=CC(O)=CC=C1)=O
Shipping ConditionSmall Molecules with Blue Ice, Modified Nucleotides with Dry Ice.
General tips We do not recommend long-term storage for the solution, please use it up soon.

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