9622. Tricarballylic Acid
Nomenclature
CAS number: 99-14-9
1,2,3-Propanetricarboxylic acid; β-carboxyglutaric acid. C6H8O6; mol wt 176.12.
C 40.92%, H 4.58%, O 54.51%.
Description and references
Natural product produced by rumen bacteria; structural component of fumonisin mycotoxins. Prepn from aconitic acid by reduction with sodium amalgam: Fittig, Ann. 314, 15 (1901); by hydrolysis of ethyl propane-1,1,2,3-tetracarboxylate: Clarke, Murray, Org. Synth. coll. vol. I (2nd ed., 1941) p 523. Absorption spectrum: Bielecki, Henri, Ber. 46, 2596 (1913). Crystal structure: J. C. Barnes, J. D. Paton, Acta Crystallogr. C44, 758 (1988). Production by rumen microorganisms: J. B. Russell, N. Forsberg, Br. J. Nutr. 56, 153 (1986). Review of chemistry: A. S. H. Elgazwy, Curr. Org. Chem. 8, 1405-1423 (2004).
Properties
Large, orthorhombic prisms from water or ether, mp 166°. pK1 (30°): 3.49; pK2: 4.58; pK3: 5.83. At 18° 50 g dissolve in 100 ml water and 0.9 g dissolve in 100 ml ether. Quite sol in alc.Derivative
Trimethyl ester.Nomenclature
CAS number: 6138-26-7
C9H14O6; mol wt 218.20.
C 49.54%, H 6.47%, O 43.99%.