Homogentisic acid

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Homogentisic acid
Names
Preferred IUPAC name
(2,5-Dihydroxyphenyl)acetic acid
Other names
Melanic acid
Identifiers
3D model (
JSmol
)
ChEBI
ChemSpider
DrugBank
ECHA InfoCard
 100.006.540 Edit this at Wikidata
KEGG
MeSH Homogentisic+acid
UNII
  • InChI=1S/C8H8O4/c9-6-1-2-7(10)5(3-6)4-8(11)12/h1-3,9-10H,4H2,(H,11,12) checkY
    Key: IGMNYECMUMZDDF-UHFFFAOYSA-N checkY
  • 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
  • O=C(O)Cc1cc(O)ccc1O
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).
checkY verify (what is checkY☒N ?)

Homogentisic acid (2,5-dihydroxyphenylacetic acid) is a

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-maleylacetoacetic acid.[6]

References

  1. PMID 10552766
    .
  2. doi:10.1139/m94-005. Archived from the original
    on 21 July 2011. Retrieved 25 February 2011.
  3. PMID 11472920
    .
  4. PMID 12501223
    .
  5. doi:10.1021/bi00634a013
    .
  6. PMID 14886367
    .
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