Homogentisic acid

Homogentisic acid
IUPAC name
(2,5-Dihydroxyphenyl)acetic acid
Other names
Melanic acid
451-13-8 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:44747 YesY
ChemSpider 759 YesY
DrugBank DB08327 YesY
ECHA InfoCard 100.006.540
KEGG C00544 YesY
MeSH Homogentisic+acid
PubChem 780
Molar mass 168.15 g·mol−1
Melting point 150 to 152 °C (302 to 306 °F; 423 to 425 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Homogentisic acid (2,5-dihydroxyphenylacetic acid) is a phenolic acid found in Arbutus unedo (strawberry-tree) honey.[1] It is also present in the bacterial plant pathogen Xanthomonas campestris pv. phaseoli[2] as well as in the yeast Yarrowia lipolytica[3] where it is associated with the production of brown pigments.

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

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, consequently associated with alkaptonuria.[4]


It is an intermediate in the catabolism of aromatic amino acids such as phenylalanine and tyrosine.


  1. Paolo Cabras; Alberto Angioni; Carlo Tuberoso; Ignazio Floris; Fabiano Reniero; Claude Guillou; Stefano Ghelli (1999). "Homogentisic Acid: A Phenolic Acid as a Marker of Strawberry-Tree (Arbutus unedo) Honey". J. Agric. Food Chem. 47 (10): 4064–4067. doi:10.1021/jf990141o.
  2. Goodwin PH, Sopher CR (1994). "Brown pigmentation of Xanthomonas campestris pv. phaseoli associated with homogentisic acid". Canadian Journal of Microbiology. 40 (1): 28–34. doi:10.1139/m94-005.
  3. Alexandra Carreira; Luísa M. Ferreira; Virgílio Loureiro (2001). "Brown Pigments Produced by Yarrowia lipolytica Result from Extracellular Accumulation of Homogentisic Acid". Appl Environ Microbiol. 67 (8): 3463–3468. doi:10.1128/AEM.67.8.3463-3468.2001.
  4. Phornphutkul C, Introne WJ, Perry MB, et al. (2002). "Natural history of alkaptonuria". New England Journal of Medicine. 347 (26): 2111–21. doi:10.1056/NEJMoa021736. PMID 12501223.
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