Synthesis of 3-Oxo-α-ionol Ethyl Carbonate and its Conversion to Megastigmatrienones in Tobacco Smoke

Abstract 3-Oxo-α-ionol ethyl carbonate, a precursor of megastigmatrienones was prepared by reduction of α-ionone to α-ionol, followed by esterification with ethyl chloroformate and then by oxidation with t-butyl chromate. The total yield was about 23%. Infrared (IR) and mass spectra of this compound were determined. Upon smoking, cigarettes to which 0.002% by weight of the titled compound was added had an improved and more harmonious flavor. The smoke was sweeter and had a cleaner after taste. Experimental results suggest that the title compound added to the tobacco pyrolyzes to form megastigmatrienones during smoking.