10068. Xanthurenic Acid
Nomenclature
CAS number: 59-00-7
4,8-Dihydroxy-2-quinolinecarboxylic acid; 4,8-dihydroxyquinaldic acid. C10H7NO4; mol wt 205.17.
C 58.54%, H 3.44%, N 6.83%, O 31.19%.
Description and references
Excreted by pyridoxine-deficient animals after the ingestion of tryptophan. Isoln from the urine of albino rats fed almost exclusively on fibrin: Musajo, Gazz. Chim. Ital. 67, 165 (1937). Synthesis from ethyl oxalacetate and o-anisidine: Musajo, Minchilli, Ber. 74, 1842 (1941); Mebane, Oroshnik, J. Am. Chem. Soc. 73, 3520 (1951); Furst, Olsen, J. Org. Chem. 16, 412 (1951).
Properties
Sulfur-yellow crystals, mp 286°. uv max (water): 243, 342 nm (ε 30000, 6500). Insol in water. Sol in aq alkali hydroxides and carbonates (yellow solns) and in hot dil HCl. It gives a red color with Millon reagent, intense ruby-red with alkali diazobenzenesulfonates, and intense green with FeSO4. When the acid is dissolved in very dil NaHCO3, the green color with FeSO4 is still visible at a diln of 1:200,000.Derivative
Methyl ester.C11H9NO4; mol wt 219.19.
C 60.28%, H 4.14%, N 6.39%, O 29.20%.