Homogentisic acid

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Homogentisic acid
IUPAC name	2-(2,5-dihydroxyphenyl)acetic acid
Identifiers
CAS number	[451-13-8]
PubChem	780
MeSH	Homogentisic+acid
SMILES	C1=CC(=C(C=C1O)CC(=O)O)O
Properties
Molecular formula	C8H8O4
Molar mass	168.147 g/mol
Melting point	150°C to 152°C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Homogentisic acid is the common name for 2,5-dihydroxyphenylacetic acid.

It is less commonly known as "Melanic acid", the name chosen by William Prout.

[edit] 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.

[edit] See also

• homogentisate 1,2-dioxygenase

v • d • e Amino acid metabolism metabolic intermediates K→acetyl-CoA lysine→ Saccharopine - Allysine - Alpha-aminoadipate - Alpha-ketoadipic acid - Glutaryl-CoA - Glutaconyl-CoA - Crotonyl-CoA - Beta-hydroxybutyryl-CoA leucine→ Alpha-ketoisocaproic acid - 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→glutamate histidine→ Urocanic acid - Imidazol-4-one-5-propionic acid - Formiminoglutamic acid - Glutamate-1-semialdehyde proline→ 1-Pyrroline-5-carboxylic acid arginine→ Ornithine - Putrescine - Agmatine G→propionyl-CoA methionine→ S-Adenosyl methionine - S-Adenosyl-L-homocysteine - Homocysteine - Cystathionine - alpha-Ketobutyric acid isoleucine→ 2,3-Dihydroxy-3-methylpentanoic acid - 2-Methylbutyryl-CoA - Tiglyl-CoA - 2-methylacetoacetyl-CoA valine→ Alpha-ketoisovalerate - Isobutyryl-CoA - Methacrylyl-CoA - 3-Hydroxyisobutyryl-CoA - 3-Hydroxyisobutyrate - 2-methyl-3-oxopropanoate threonine→ Alpha-ketobutyric acid propionyl-CoA→ Methylmalonyl-CoA G→fumarate phenylalanine→tyrosine→ 4-Hydroxyphenylpyruvic acid - Homogentisic acid - 4-Maleylacetoacetate Other cysteine+glutamate→glutathione gamma-Glutamylcysteine glycine→creatine Glycocyamine - Phosphocreatine - Creatinine Other Glycerate 3-phosphate (serine) - Cysteine sulfinic acid see also enzymes, disorders