Xanthurenic acid

Source: Wikipedia, the free encyclopedia.
Xanthurenic acid[1]
Names
Preferred IUPAC name
4,8-Dihydroxyquinoline-2-carboxylic acid
Other names
Xanthuric acid
Xanthurenate
8-Hydroxykynurenic acid
4,8-Dihydroxyquinaldic acid
Identifiers
3D model (
JSmol
)
ChEBI
ChemSpider
ECHA InfoCard
 100.000.373 Edit this at Wikidata
EC Number
  • 200-410-1
KEGG
UNII
  • InChI=1S/C10H7NO4/c12-7-3-1-2-5-8(13)4-6(10(14)15)11-9(5)7/h1-4,12H,(H,11,13)(H,14,15) ☒N
    Key: FBZONXHGGPHHIY-UHFFFAOYSA-N ☒N
  • InChI=1/C10H7NO4/c12-7-3-1-2-5-8(13)4-6(10(14)15)11-9(5)7/h1-4,12H,(H,11,13)(H,14,15)
    Key: FBZONXHGGPHHIY-UHFFFAOYAE
  • OC2=CC(C(O)=O)=NC1=C(O)C=CC=C12
Properties
C10H7NO4
Molar mass 205.169 g·mol−1
Appearance Yellow crystals
Melting point 286 °C (547 °F; 559 K)
Insoluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Xanthurenic acid, or xanthurenate, is a metabolic intermediate that accumulates and is excreted by pyridoxine (vitamin B6) deficient animals after the ingestion of tryptophan.[1][2]

Xanthurenic acid is suspected to be an

vesicular glutamate transporters (Ki = 0.19 mM).[4]

In 2015[update] researchers reported a marked reduction of xanthurenic acid levels in the serum of patients with schizophrenia.[5] A recent meta-analysis showed that blood xanthurenic acid levels are lower in individuals suffering from bipolar disorder as well.[6]

Xanthurenic acid has also been shown to induce gametogenesis of Plasmodium falciparum, the parasite that causes malaria.[7][8] It is found in the gut of the Anopheles mosquito.

See also

References

  1. ^ a b Merck Index, 11th Edition, 9977.
  2. ^ Xanthurenic acid at Sigma-Aldrich
  3. S2CID 37921378
    .
  4. S2CID 39853026
    .
  5. PMID 26643205
    .
  6. S2CID 224314102
    .
  7. S2CID 2584314
    .
  8. PMID 9575140
    .