Homogentisic acid

Homogentisic acid
Names
	Preferred 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;
UNII	NP8UE6VF08 ;
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−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). verify (what is ?) Infobox references

Homogentisic acid (2,5-dihydroxyphenylacetic acid) is a phenolic acid 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 hippopotamuses.

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

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