Homogentisic acid
| Homogentisic acid | |
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(2,5-Dihydroxyphenyl)acetic acid |
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Other names
Melanic acid |
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| Identifiers | |
| CAS number | 451-13-8  |
| PubChem | 780 |
| ChemSpider | 759 |
| DrugBank | DB08327 |
| KEGG | C00544 |
| MeSH | Homogentisic+acid |
| ChEBI | CHEBI:44747 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C8H8O4 |
| Molar mass | 168.15 g mol−1 |
| Melting point |
150-152 °C, 423-425 K, 302-306 °F |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 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.
[edit] 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.[4]
[edit] Intermediate
It is an intermediate in the metabolism of aromatic amino acids such as phenylalanine and tyrosine.
[edit] References
- ^ 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.
- ^ 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. http://cat.inist.fr/?aModele=afficheN&cpsidt=3978055.
- ^ 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.
- ^ 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. http://content.nejm.org/cgi/content/full/347/26/2111.
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