Homogentisic acid

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Homogentisic acid
Homogentisic acid.svg
Identifiers
CAS number 451-13-8 YesY
PubChem 780
ChemSpider 759 YesY
DrugBank DB08327
KEGG C00544 YesY
MeSH Homogentisic+acid
ChEBI CHEBI:44747 YesY
Jmol-3D images Image 1
Properties
Molecular formula C8H8O4
Molar mass 168.15 g mol−1
Melting point 150 to 152 °C (302 to 306 °F; 423 to 425 K)
Except where noted otherwise, 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[edit]

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]

Intermediate[edit]

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

References[edit]

  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. 
  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. doi:10.1139/m94-005. 
  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.