MOLECULE

4-Hydroxyphenylpyruvic acid

4-Hydroxyphenylpyruvic acid, also known as 4-hydroxy a-oxobenzenepropanoate or (p-hydroxyphenyl)pyruvate, belongs to the class of organic compounds known as phenylpyruvic acid derivatives. Phenylpyruvic acid derivatives are compounds containing a phenylpyruvic acid moiety, which consists of a phenyl group substituted at the second position by an pyruvic acid. 4-Hydroxyphenylpyruvic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 4-Hydroxyphenylpyruvic acid exists in all living species, ranging from bacteria to humans. Within humans, 4-hydroxyphenylpyruvic acid participates in a number of enzymatic reactions. In particular, 4-hydroxyphenylpyruvic acid and L-glutamic acid can be biosynthesized from L-tyrosine and oxoglutaric acid; which is catalyzed by the enzyme tyrosine aminotransferase. In addition, 4-hydroxyphenylpyruvic acid can be converted into homogentisic acid through its interaction with the enzyme 4-hydroxyphenylpyruvate dioxygenase. An oxo carboxylic acid that is pyruvic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group. In humans, 4-hydroxyphenylpyruvic acid is involved in the metabolic disorder called tyrosinemia, transient, of the newborn. Outside of the human body, 4-Hydroxyphenylpyruvic acid has been detected, but not quantified in, several different foods, such as black chokeberries, limes, hazelnuts, pepper (c. baccatum), and dandelions. This could make 4-hydroxyphenylpyruvic acid a potential biomarker for the consumption of these foods. 4-Hydroxyphenylpyruvic acid is a potentially toxic compound. 4-Hydroxyphenylpyruvic acid, with regard to humans, has been found to be associated with several diseases such as deafness, onychodystrophy, osteodystrophy, mental retardation, and seizures syndrome, attachment loss, colorectal cancer, and periodontal probing depth; 4-hydroxyphenylpyruvic acid has also been linked to the inborn metabolic disorder phenylketonuria. 4-Hydroxyphenylpyruvic acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.