Title: Prephenic Acid
CAS Registry Number: 126-49-8
CAS Name: 1-Carboxy-4-hydroxy-a-oxo-2,5-cyclohexadiene-1-propanoic acid
Additional Names: 1-carboxy-4-hydroxy-2,5-cyclohexadiene-1-pyruvic acid
Molecular Formula: C10H10O6
Molecular Weight: 226.18
Percent Composition: C 53.10%, H 4.46%, O 42.44%
Literature References: Non-aromatic biosynthetic intermediate that represents a secondary branch-point in the pathway from chorismic acid to phenylalanine and tyrosine, q.q.v., in many organisms. Isoln from cultures of mutant Escherichia coli: B. D. Davis, Science 118, 251 (1953). Characterized as cryst Ba salt: U. Weiss et al., ibid. 119, 774 (1954); R. L. Metzenberg, H. K. Mitchell, Arch. Biochem. Biophys. 64, 51 (1956). Structure: H. Plieninger, G. Keilich, Z. Naturforsch. 16b, 81 (1961). Synthetic approaches: H. Plieninger, Angew. Chem. Int. Ed. 1, 367 (1962). Total synthesis of disodium salt: S. Danishevsky, M. Hirama, J. Am. Chem. Soc. 99, 7740 (1977); S. Danishevsky et al., ibid. 101, 7013 (1979); W. Gramlich, H. Plieninger, Ber. 112, 1571 (1979). Review: U. Weiss, J. M. Edwards, The Biosynthesis of Aromatic Compounds (Wiley, New York, 1980) pp 144-184. See also shikimic acid.
Derivative Type: Barium salt monohydrate
Molecular Formula: C10H8BaO6.H2O
Molecular Weight: 379.51
Percent Composition: C 31.65%, H 2.66%, Ba 36.19%, O 29.51%
Properties: Crystals from water + methanol or water + pyridine.
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