Title: Thujic Acid
CAS Registry Number: 499-89-8
CAS Name: 5,5-Dimethyl-1,3,6-cycloheptatriene-1-carboxylic acid
Additional Names: 4,4-dimethylcyclohepta-2,5,7-trienecarboxylic acid; dehydroperillic acid
Molecular Formula: C10H12O2
Molecular Weight: 164.20
Percent Composition: C 73.15%, H 7.37%, O 19.49%
Literature 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 e 4.3, 3.7); min: 240 nm (log e 3.0).
Melting point: mp 88-89°
Absorption maximum: uv max: 220, 280 nm (log e 4.3, 3.7); min: 240 nm (log e 3.0)
Derivative Type: Methyl ester
Molecular Formula: C11H14O2
Molecular Weight: 178.23
Percent Composition: C 74.13%, H 7.92%, O 17.95%
Properties: Crystals, mp 34.5-35° or liq with pleasant odor, bp14 112-113°. d422 1.0225. nD22 1.5130.
Melting point: mp 34.5-35°
Boiling point: bp14 112-113°
Index of refraction: nD22 1.5130
Density: d422 1.0225
Derivative Type: Hexahydrothujic acid
Molecular Formula: C10H18O2
Molecular Weight: 170.25
Percent Composition: C 70.55%, H 10.66%, O 18.80%
Properties: Liq, bp14 150-152°. nD20 1.4671.
Boiling point: bp14 150-152°
Index of refraction: nD20 1.4671
|