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Homogentisic acid

Names
IUPAC name (2,5-Dihydroxyphenyl)acetic acid
Other names Melanic acid
Identifiers
CAS Number	451-13-8
3D model (JSmol)	Interactive image
ChEBI	CHEBI:44747
ChemSpider	759
DrugBank	DB08327
ECHA InfoCard	100.006.540
KEGG	C00544
MeSH	Homogentisic+acid
PubChem CID	780
CompTox Dashboard (EPA)	DTXSID1060005
InChI InChI=1S/C8H8O4/c9-6-1-2-7(10)5(3-6)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)Key: IGMNYECMUMZDDF-UHFFFAOYSA-N InChI=1/C8H8O4/c9-6-1-2-7(10)5(3-6)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)Key: IGMNYECMUMZDDF-UHFFFAOYAK
SMILES O=C(O)Cc1cc(O)ccc1O
Properties
Chemical formula	C8H8O4
Molar mass	168.148 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y verify (what is  ?) Infobox references

Homogentisic acid (2,5-dihydroxyphenylacetic acid) is a phenolic acid 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 less commonly known as melanic acid, the name chosen by William Prout.

Human pathology

Accumulation of excess homogentisic acid is a result of the failure of the enzyme homogentisic acid 1,2-dioxygenase (typically due to a mutation) and is associated with alkaptonuria.

Intermediate

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

References

1. Paolo Cabras, Alberto Angioni, Carlo Tuberoso, Ignazio Floris, Fabiano Reniero, Claude Guillou and 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
2. Goodwin PH and Sopher CR (1994). "Brown pigmentation of Xanthomonas campestris pv. phaseoli associated with homogentisic acid". Canadian Journal of Microbiology. 40 (1): 28–34.
3. Alexandra Carreira, Luísa M. Ferreira and 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 Medicine. 347 (26): 2111–21. doi:10.1056/NEJMoa021736. PMID 12501223. {{cite journal}}: Explicit use of et al. in: |author= (help)CS1 maint: multiple names: authors list (link)

• Use dmy dates from March 2011
• Hydroquinones
• Carboxylic acids