9391. Thujic Acid
Nomenclature
CAS number: 499-89-8
5,5-Dimethyl-1,3,6-cycloheptatriene-1-carboxylic acid; 4,4-dimethylcyclohepta-2,5,7-trienecarboxylic acid; dehydroperillic acid. C10H12O2; mol wt 164.20.
C 73.15%, H 7.37%, O 19.49%.
Description and references
Antibiotic substance from heartwood of Thuja plicata D. Don, Cupressaceae (Western red cedar). Isoln: Anderson, Sherrard, J. Am. Chem. Soc. 55, 3813 (1933); Erdtman, Gripenberg, Acta Chem. Scand. 2, 625 (1948). Structure: Gripenberg, ibid. 3, 1137 (1949); 5, 995 (1951); 10, 487 (1956); Davis, Tulinsky, Tetrahedron Lett. 1962, 839.
Properties
Crystals from petr ether, mp 88-89°. uv max: 220, 280 nm (log ε 4.3, 3.7); min: 240 nm (log ε 3.0).Derivative
Methyl ester.C11H14O2; mol wt 178.23.
C 74.13%, H 7.92%, O 17.95%.
Properties
Crystals, mp 34.5-35° or liquid with pleasant odor, bp14 112-113°. d422 1.0225. nD22 1.5130.Derivative
Hexahydrothujic acid.C10H18O2; mol wt 170.25.
C 70.55%, H 10.66%, O 18.80%.