Thujone
Title: Thujone
CAS Name: 4-Methyl-1-(1-methylethyl)bicyclo[3.1.0]hexan-3-one
Additional Names: 3-thujanone
Molecular Formula: C10H16O
Molecular Weight: 152.23
Percent Composition: C 78.90%, H 10.59%, O 10.51%
Literature References: A constituent of many essential oils; present in thuja, etc. Equilibrium mixture contains 33% a-thujone and 67% b-thujone: Eastman, Winn, J. Am. Chem. Soc. 82, 5908 (1960). a- and b-Thujones differ only in the stereochemistry of the 4-methyl group. Conformation: Hach et al., Tetrahedron Lett. 1970, 3175. Chemistry: J. P. Kutney et al., Bioorg. Chem. 7, 289 (1978); eidem, Can. J. Chem. 57, 3145 (1979); 58, 2641 (1980). Toxicity study: K. C. Rice, R. S. Wilson, J. Med. Chem. 19, 1054 (l976). Review: J. L. Simonsen, The Terpenes vol. II (University Press, Cambridge, 1949) pp 32-52.
Properties: Colorless or almost colorless liquid. uv max (isooctane): 300 nm (e 23). Practically insol in water. Sol in alc and many other organic solvents. LD50 s.c. in mice: 134.2 mg/kg (Rice, Wilson).
Absorption maximum: uv max (isooctane): 300 nm (e 23)
Toxicity data: LD50 s.c. in mice: 134.2 mg/kg (Rice, Wilson)
 
Derivative Type: a-Thujone
CAS Registry Number: 546-80-5
Additional Names: (1S,4R,5R)-(-)-3-Thujanone
Properties: bp17 83.8-84.1°. d425 0.9109. nD15 1.4490. [a]D20 -19.2°. LD50 s.c. in mice: 87.5 mg/kg (Rice, Wilson).
Boiling point: bp17 83.8-84.1°
Optical Rotation: [a]D20 -19.2°
Index of refraction: nD15 1.4490
Density: d425 0.9109
Toxicity data: LD50 s.c. in mice: 87.5 mg/kg (Rice, Wilson)
 
Derivative Type: b-Thujone
CAS Registry Number: 471-15-8
Additional Names: d-Isothujone; (1S,4S,5R)-(+)-3-thujanone
Properties: bp17 85.7-86.2°. d425 0.9135. nD25 1.4500. [a]D15 +72.5°. LD50 s.c. in mice: 442.2 mg/kg (Rice, Wilson).
Boiling point: bp17 85.7-86.2°
Optical Rotation: [a]D15 +72.5°
Index of refraction: nD25 1.4500
Density: d425 0.9135
Toxicity data: LD50 s.c. in mice: 442.2 mg/kg (Rice, Wilson)
 
CAUTION: Ingestion may cause convulsions.

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