Homogentisic acid
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| Names | |
|---|---|
| IUPAC name
(2,5-Dihydroxyphenyl)acetic acid
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| Other names
Melanic acid
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| Identifiers | |
451-13-8  |
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| 3D model (Jmol) | Interactive image |
| ChEBI | CHEBI:44747 |
| ChemSpider | 759 |
| DrugBank | DB08327 |
| ECHA InfoCard | 100.006.540 |
| KEGG | C00544 |
| MeSH | Homogentisic+acid |
| PubChem | 780 |
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| Properties | |
| C8H8O4 | |
| Molar mass | 168.15 g·mol−1 |
| Melting point | 150 to 152 °C (302 to 306 °F; 423 to 425 K) |
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Except where otherwise noted, 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]
- ^ Paolo Cabras; Alberto Angioni; Carlo Tuberoso; Ignazio Floris; Fabiano Reniero; Claude Guillou; 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, 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.
- ^ Alexandra Carreira; Luísa M. Ferreira; 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 of Medicine. 347 (26): 2111–21. doi:10.1056/NEJMoa021736. PMID 12501223.
