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Homogentisic acid

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Title: Homogentisic acid  
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Subject: Tyrosine, Alkaptonuria, Phenols, Methylmalonyl-CoA, Beta-Hydroxybutyryl-CoA
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Homogentisic acid

Homogentisic acid
Identifiers
CAS number  YesY
PubChem
ChemSpider  YesY
DrugBank
KEGG  YesY
MeSH
ChEBI  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)
 YesY   YesY/N?)

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]

Intermediate

It is an intermediate in the catabolism 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.  
  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.  
  4. ^ Phornphutkul C, Introne WJ, Perry MB, et al. (2002). "Natural history of alkaptonuria". New England Journal Medicine 347 (26): 2111–21.  
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