4737. Homogentisic Acid
Nomenclature
Description and references
An important intermediate in metabolism of tyrosine and phenylalanine, q.q.v.. Occurs in plants and in the urine of alkaptonurics: Garrod, Inborn Errors of Metabolism (Oxford Medical Publications, London, 1923, and later). Isoln from alkaptonuric urine: Mrner, Z. Physiol. Chem. 117, 85 (1921). Synthesis from 2,5-dihydroxymandelic acid or from 2,5-dihydroxyphenylglyoxylic acid by boiling with fuming HI: Neubauer, Flatow, ibid. 52, 395 (1907). Alternate syntheses: L. DeForrest Abbott, J. D. Smith, J. Biol. Chem. 179, 365 (1949); S. B. Bostock, A. H. Renfrew, Synthesis 1978, 66; J. L. Bloomer, K. M. Damodaran, ibid. 1980, 111. Biosynthesis from tyrosine: Davies et al., J. Chem. Soc. 1964, 3126. Metabolic studies: W. E. Knox, M. LeMay-Knox, Biochem. J. 49, 686 (1951); B. N. LaDu, V. G. Zannoni, J. Biol. Chem. 217, 777 (1955).
