Homogentisic acid (2,5-dihydroxyphenylacetic acid) is a

phenolic acid Phenolic acids or phenolcarboxylic acids are types of aromatic acid compounds. Included in that class are substances containing a phenolic ring and an organic carboxylic acid function (C6-C1 skeleton). Two important naturally occurring types of ph ...

usually found in '' Arbutus unedo'' (strawberry-tree) honey. It is also present in the bacterial plant pathogen ''Xanthomonas campestris'' pv. ''phaseoli'' as well as in the yeast '' Yarrowia lipolytica'' where it is associated with the production of brown pigments. It is oxidatively dimerised to form hipposudoric acid, one of the main constituents of the 'blood sweat' of

hippopotamus The hippopotamus ( ; : hippopotamuses or hippopotami; ''Hippopotamus amphibius''), also called the hippo, common hippopotamus, or river hippopotamus, is a large semiaquatic mammal native to sub-Saharan Africa. It is one of only two exta ...

es. It is less commonly known as melanic acid, the name chosen by

William Prout William Prout FRS (; 15 January 1785 – 9 April 1850) was an English chemist, physician, and natural theologian. He is remembered today mainly for what is called Prout's hypothesis. Biography Prout was born in Horton, Gloucestershire in 1 ...

Human pathology

Accumulation of excess homogentisic acid and its oxide, named alkapton, is a result of the failure of the enzyme homogentisic acid 1,2-dioxygenase (typically due to a mutation) in the degradative pathway of

tyrosine -Tyrosine or tyrosine (symbol Tyr or Y) or 4-hydroxyphenylalanine is one of the 20 standard amino acids that are used by cells to synthesize proteins. It is a non-essential amino acid with a polar side group. The word "tyrosine" is from the Gr ...

, consequently associated with alkaptonuria.

Intermediate

It is an intermediate in the

catabolism Catabolism () is the set of metabolic pathways that breaks down molecules into smaller units that are either oxidized to release energy or used in other anabolic reactions. Catabolism breaks down large molecules (such as polysaccharides, lipids ...

of aromatic amino acids such as

phenylalanine Phenylalanine (symbol Phe or F) is an essential α-amino acid with the formula . It can be viewed as a benzyl group substituted for the methyl group of alanine, or a phenyl group in place of a terminal hydrogen of alanine. This essential amino a ...

and

4-Hydroxyphenylpyruvate 4-Hydroxyphenylpyruvic acid (4-HPPA) is an intermediate in the metabolism of the amino acid phenylalanine. The aromatic side chain of phenylalanine is hydroxylated by the enzyme phenylalanine hydroxylase to form tyrosine. The conversion from tyr ...

(produced by

transamination Transamination is a chemical reaction that transfers an amino group to a ketoacid to form new amino acids. This pathway is responsible for the deamination of most amino acids. This is one of the major degradation pathways which convert essentia ...

of tyrosine) is acted upon by the enzyme

4-hydroxyphenylpyruvate dioxygenase 4-Hydroxyphenylpyruvate dioxygenase (HPPD), also known as α-ketoisocaproate dioxygenase (KIC dioxygenase), is an Fe(II)-containing non-heme oxygenase that catalyzes the second reaction in the catabolism of tyrosine - the conversion of 4-hydro ...

to yield homogentisate. If active and present, the enzyme homogentisate 1,2-dioxygenase further degrades homogentisic acid to yield

4-maleylacetoacetic acid 4-Maleylacetoacetate (4-maleylacetoacetatic acid) is an intermediate in the metabolism of tyrosine. It is converted to fumarylacetoacetate by the enzyme 4-maleylacetoacetate cis-trans-isomerase. Gluthathione coenzymatically helps in conversion to ...

References

{{DEFAULTSORT:Homogentisic Acid Hydroquinones Acetic acids Hydroxy acids