3-Hydroxyphenylacetic acid

3-Hydroxyphenylacetic acid is an organic compound with the chemical formula C₈H₈O₃. It is a type of phenolic acid, which is a subclass of aromatic acids. This compound is characterized by the presence of a hydroxyl group (-OH) attached to the benzene ring of phenylacetic acid.

Structure and Properties

3-Hydroxyphenylacetic acid consists of a benzene ring with a hydroxyl group at the third position and an acetic acid moiety attached to the benzene ring. The presence of the hydroxyl group makes it a phenolic compound, which contributes to its acidic properties.

• Molecular Formula: C₈H₈O₃
• Molar Mass: 152.15 g/mol
• Appearance: White crystalline solid
• Solubility: Soluble in water, alcohol, and ether

Biosynthesis and Metabolism

3-Hydroxyphenylacetic acid is a metabolite of the amino acid tyrosine. It is produced in the human body through the catabolism of tyrosine by the action of specific enzymes. The metabolic pathway involves the conversion of tyrosine to 3-hydroxyphenylpyruvic acid, which is then further metabolized to 3-hydroxyphenylacetic acid.

Biological Significance

In humans, 3-hydroxyphenylacetic acid is found in urine as a normal metabolic product. It is also a significant compound in the study of certain metabolic disorders. Elevated levels of 3-hydroxyphenylacetic acid in urine can be indicative of disorders such as phenylketonuria or other inborn errors of metabolism related to tyrosine degradation.

Applications

3-Hydroxyphenylacetic acid is used in biochemical research to study metabolic pathways involving aromatic amino acids. It is also used as a reference compound in the analysis of urine samples for diagnostic purposes.

Also see

• Phenylacetic acid
• Tyrosine
• Phenylketonuria
• Aromatic amino acids