Homogentisic acid

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Structural formula
Structural formula of homogentisic acid
General
Surname Homogentisic acid
other names

2,5-dihydroxyphenylacetic acid

Molecular formula C 8 H 8 O 4
Brief description

beige solid

External identifiers / databases
CAS number 451-13-8
EC number 207-192-7
ECHA InfoCard 100.006.540
PubChem 780
ChemSpider 759
DrugBank DB08327
Wikidata Q416054
properties
Molar mass 168.15 g mol −1
Physical state

firmly

Melting point

152–154 ° C (monohydrate)

safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 315-319-335
P: 261-305 + 351 + 338
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Homogentisic acid is an intermediate product of the breakdown of the amino acids phenylalanine and tyrosine and is present as an anion ( homogenate ) at physiological pH values . It is converted into 4-maleyl acetic acid by the enzyme homogenate dioxygenase ( EC 1.13.11.5 ):  

Conversion of homogenates to 4-maleyl acetoacetate. This is catalyzed by the homogenate 1,2-dioxygenase with consumption of oxygen.

As a result, acetoacetic acid and fumaric acid are formed , which can be fed into the citric acid cycle .

In alkaptonuria , a metabolic disease , the enzyme is absent or not present in sufficient quantities. "Alkapton" is the oxidized, black-brown form of the homogenate.

See also

Individual evidence

  1. ↑ a b c data sheet Homogentisic acid from Sigma-Aldrich , accessed on April 4, 2011 ( PDF ).
  2. ↑ a b entry on homogentisic acid. In: Römpp Online . Georg Thieme Verlag, accessed on June 16, 2014.