Homogentisic acid
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| Names | |
|---|---|
| Preferred IUPAC name
(2,5-Dihydroxyphenyl)acetic acid | |
| Other names
Melanic acid
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| Identifiers | |
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3D model (JSmol)
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| MeSH | Homogentisic+acid |
PubChem CID
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| Properties | |
| 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).
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Template:Chembox Footer/trackingTemplate:Short description
Homogentisic acid (2,5-dihydroxyphenylacetic acid) is a phenolic acid usually 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 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.
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.
4-Hydroxyphenylpyruvate (produced by transamination of tyrosine) is acted upon by the enzyme 4-hydroxyphenylpyruvate dioxygenase to yield homogentisate.[5] If active and present, the enzyme homogentisate 1,2-dioxygenase further degrades homogentisic acid to yield 4-maleylacetoacetic acid.[6]
References
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- ^ Page Module:Citation/CS1/styles.css has no content.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. Bibcode:1999JAFC...47.4064C. doi:10.1021/jf990141o. PMID 10552766.
- ^ Page Module:Citation/CS1/styles.css has no content.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. Archived from the original on 21 July 2011. Retrieved 25 February 2011.
- ^ Page Module:Citation/CS1/styles.css has no content.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. Bibcode:2001ApEnM..67.3463C. CiteSeerX 10.1.1.319.523. doi:10.1128/AEM.67.8.3463-3468.2001. PMC 93044. PMID 11472920.
- ^ Page Module:Citation/CS1/styles.css has no content.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.
- ^ Page Module:Citation/CS1/styles.css has no content.Lindstedt, Sven; Odelhog, Birgit; Rundgren, Marianne (1977). "Purification and Some Properties of 4-Hydroxyphenylpyruvate Dioxygenase from Pseudomonas sp. P.J. 814". Biochemistry. 16 (15): 3369–3377. doi:10.1021/bi00634a013. PMID 889802.
- ^ Page Module:Citation/CS1/styles.css has no content.Knox WE, LeMay-Knox M (October 1951). "The oxidation in liver of l-tyrosine to acetoacetate through p-hydroxyphenylpyruvate and homogentisic acid". The Biochemical Journal. 49 (5): 686–93. doi:10.1042/bj0490686. PMC 1197578. PMID 14886367.
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