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Muconic acid (hexa-2:4-diene-1:6-dioic acid) was first discovered to be a metabolite of benzene by There are three geometrical isomers of muconic acid, namely, cis-c8, ci8-trans and tran8-trana, and in every instance in which the isolation ofmuconic acid from the urine of men and animals dosed with benzene has been reported, the isomer isolated has been the trans-trans form (Jaff6, 1909; Fuchs & So6s, 1916-17; Mori, 1918; Neumaerker, 1923; Thierfelder & Klenk, 1924; Drummond & Finar, 1938; Bernhard & Gressly, 1941). If muconic acid is formed in vivo by the opening of the benzene ring, then it would be expected on stereochemical grounds that the isomer produced would be the cis-ci-isomer; the oxidation of phenol or of catechol with peracetic acid does, in fact, give rise to cia-cis-muconic acid (Boeseken & Engelberts, 1931; Boeseken & Kerkhoven, 1932; Elvidge et al. 1950a).
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Parke et al. (1952) studied this question.
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