- Homogentisic acid
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Homogentisic acid 
(2,5-Dihydroxyphenyl)acetic acidOther namesMelanic acidIdentifiers CAS number 451-13-8 PubChem 780 ChemSpider 759 
DrugBank DB08327 KEGG C00544 MeSH Homogentisic+acid ChEBI CHEBI:44747 Jmol-3D images Image 1 - O=C(O)Cc1cc(O)ccc1O
- InChI=1S/C8H8O4/c9-6-1-2-7(10)5(3-6)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)
Key: IGMNYECMUMZDDF-UHFFFAOYSA-N
InChI=1/C8H8O4/c9-6-1-2-7(10)5(3-6)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)
Key: IGMNYECMUMZDDF-UHFFFAOYAK
Properties Molecular formula C8H8O4 Molar mass 168.15 g mol−1 Melting point 150-152 °C, 423-425 K, 302-306 °F
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)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
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]
Intermediate
It is an intermediate in the metabolism of aromatic amino acids such as phenylalanine and tyrosine.
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.
K→acetyl-CoA G G→pyruvate→citrateG→glutamate→
α-ketoglutarateotherα-Ketoisovaleric acid · Isobutyryl-CoA · Methacrylyl-CoA · 3-Hydroxyisobutyryl-CoA · 3-Hydroxyisobutyric acid · 2-Methyl-3-oxopropanoic acidG→fumarateG→oxaloacetatesee urea cycleOther biochemical families: prot · nucl · carb (glpr, alco, glys) · lipd (fata/i, phld, strd, gllp, eico) · amac/i · ncbs/i · ttpy/iMonohydroxybenzoic acids Dihydroxybenzoic acids Gentisic acid | Homogentisic acid | Orsellinic acid | Protocatechuic acid | 2,3-Dihydroxybenzoic acid | 2,4-Dihydroxybenzoic acid | 2,6-Dihydroxybenzoic acid | 3,5-Dihydroxybenzoic acidTrihydroxybenzoic acids Bergenin | Chebulic acid | Ethyl gallate | Eudesmic acid | Gallic acid | Norbergenin | Phloroglucinol carboxylic acid | Syringic acid | TheogallinCategories:- Hydroquinones
- Carboxylic acids
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