MOLECULE

Homogentisic acid

Homogentisic acid, also known as homogentisate or acid, homogentisic, belongs to the class of organic compounds known as 2(hydroxyphenyl)acetic acids. These are phenylacetic acids that carry a hydroxyl group at the 2-position. A dihydroxyphenylacetic acid having the two hydroxy substituents at the 2- and 5-positions. Homogentisic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Homogentisic acid exists in all living organisms, ranging from bacteria to humans. Within humans, homogentisic acid participates in a number of enzymatic reactions. In particular, homogentisic acid can be biosynthesized from 4-hydroxyphenylpyruvic acid through the action of the enzyme 4-hydroxyphenylpyruvate dioxygenase. In addition, homogentisic acid can be converted into maleylacetoacetic acid; which is mediated by the enzyme homogentisate 1,2-dioxygenase. In humans, homogentisic acid is involved in the metabolic disorder called tyrosinemia, transient, of the newborn. Outside of the human body, Homogentisic acid has been detected, but not quantified in, several different foods, such as green beans, prunus (cherry, plum), black cabbages, hyacinth beans, and gram beans. This could make homogentisic acid a potential biomarker for the consumption of these foods. Homogentisic acid is a potentially toxic compound. Homogentisic acid, with regard to humans, has been found to be associated with several diseases such as eosinophilic esophagitis, ulcerative colitis, and crohn's disease; homogentisic acid has also been linked to the inborn metabolic disorder alkaptonuria. Homogentisic acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.