10257. Cinnamyl Acetate
Nomenclature
CAS number: 103-54-8
3-Phenyl-2-propen-1-ol 1-acetate; 3-acetoxy-1-phenylpropene. C11H12O2; mol wt 176.21.
C 74.98%, H 6.86%, O 18.16%.
Description and references
The naturally occurring trans-form is a constituent of the essential oils of various species of cinnamon, q.v. Isoln from oil of cassia, Cinnamomum cassia Blume: F. D. Dodge, A. E. Sherndal, Ind. Eng. Chem. 7, 1055 (1915) DOI; F. D. Dodge, ibid. 10, 1005 (1918) DOI; R. ter Heide, J. Agric. Food Chem. 20, 747 (1972) DOI. Prepn: K. Hess, W. Wustrow, Ann. 437, 256 (1924) DOI. Synthesis of stereoisomers from cinnamyl alcohol and acetic anhydride: G. H. Schmid et al., J. Org. Chem. 42, 871 (1977) DOI; H. L. Goering, S. S. Kantner, ibid. 48, 721 (1983) DOI; H. Eshghi, P. Shafieyoon, J. Chem. Res. 2004, 802. Review of toxicological profile: S. P. Bhatia et al., Food Chem. Toxicol. 45, Suppl. 1, S53-S57 (2007) DOI.
Properties
Colorless to slightly yellow, oily liquid; sweet, balsamic, floral odor. bp18 140-141°. d412 1.0567. nD12 1.54415. Sol in alcohol, fixed oils. Insol in water, glycerin. LD50 orally in rats: 3.3 g/kg; dermally in rabbits: >5 g/kg (Bhatia).Derivative
trans-Form.Nomenclature
CAS number: 21040-45-9
(E)-Cinnamyl acetate. Properties
Colorless liquid, sweet-flowery-fruity, slightly balsamic odor. bp760 263°. bp10 137-139°. bp5 95°.Derivative
cis-Form.Nomenclature
CAS number: 77134-01-1
(Z)-Cinnamyl acetate.