Homogentisic acid

Homogentisic acid
Names

IUPAC name (2,5-Dihydroxyphenyl)acetic acid
Other names Melanic acid
Identifiers
CAS Number	451-13-8^Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:44747^Y
ChemSpider	759^Y
DrugBank	DB08327^Y
ECHA InfoCard	100.006.540
KEGG	C00544^Y
MeSH	Homogentisic+acid
PubChem	780
InChI InChI=1S/C8H8O4/c9-6-1-2-7(10)5(3-6)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)^Y Key: IGMNYECMUMZDDF-UHFFFAOYSA-N^Y 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
SMILES O=C(O)Cc1cc(O)ccc1O
Properties
Chemical 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 otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is ^YN ?)
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 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

↑ 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.

Amino acid metabolism metabolic intermediates

K→acetyl-CoA

lysine→	Saccharopine Allysine α-Aminoadipic acid α-Ketoadipate Glutaryl-CoA Glutaconyl-CoA Crotonyl-CoA β-Hydroxybutyryl-CoA

leucine→	α-Ketoisocaproic acid β-hydroxy β-methylbutyric acid β-hydroxy β-methylbutyryl-CoA Isovaleryl-CoA 3-Methylcrotonyl-CoA 3-Methylglutaconyl-CoA HMG-CoA

tryptophan→alanine→	N'-Formylkynurenine Kynurenine Anthranilic acid 3-Hydroxykynurenine 3-Hydroxyanthranilic acid 2-Amino-3-carboxymuconic semialdehyde 2-Aminomuconic semialdehyde 2-Aminomuconic acid Glutaryl-CoA

G→pyruvate→citrate

glycine→serine→	3-Phosphoglyceric acid glycine→creatine: Glycocyamine Phosphocreatine Creatinine

G→glutamate→
α-ketoglutarate

histidine→	Urocanic acid Imidazol-4-one-5-propionic acid Formiminoglutamic acid Glutamate-1-semialdehyde

proline→	1-Pyrroline-5-carboxylic acid

arginine→	Agmatine Ornithine Citrulline Cadaverine Putrescine

other	cysteine+glutamate→glutathione: γ-Glutamylcysteine

G→propionyl-CoA→
succinyl-CoA

valine→	α-Ketoisovaleric acid Isobutyryl-CoA Methacrylyl-CoA 3-Hydroxyisobutyryl-CoA 3-Hydroxyisobutyric acid 2-Methyl-3-oxopropanoic acid

isoleucine→	2,3-Dihydroxy-3-methylpentanoic acid 2-Methylbutyryl-CoA Tiglyl-CoA 2-Methylacetoacetyl-CoA

methionine→	generation of homocysteine: S-Adenosyl methionine S-Adenosyl-L-homocysteine Homocysteine conversion to cysteine: Cystathionine alpha-Ketobutyric acid+Cysteine

threonine→	α-Ketobutyric acid

propionyl-CoA→	Methylmalonyl-CoA

G→fumarate

phenylalanine→tyrosine→	4-Hydroxyphenylpyruvic acid Homogentisic acid 4-Maleylacetoacetic acid

G→oxaloacetate

see urea cycle

Other

Cysteine metabolism	Cysteine sulfinic acid

Phenolic acids (C6-C1) and their glycosides

Monohydroxybenzoic acids

Glycosides	p-Hydroxybenzoic acid glucoside

Acetylated	Methylparaben (Methyl p-hydroxybenzoic acid)

Dihydroxybenzoic acids

2,3-Dihydroxybenzoic acid (Hypogallic acid)
2,4-Dihydroxybenzoic acid
2,5-Dihydroxybenzoic acid (Gentisic acid)
2,6-Dihydroxybenzoic acid
3,4-Dihydroxybenzoic acid (Protocatechuic acid)
3,5-Dihydroxybenzoic acid

Acetylated	Ethyl protocatechuate Orsellinic acid

Trihydroxybenzoic acids

Glycosides	Bergenin Norbergenin Theogallin Chebulic acid

Acetylated	Ethyl gallate Eudesmic acid Methyl gallate Syringic acid

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