<abstract xmlns="http://www.w3.org/1999/xhtml">

<p>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.</p>
</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.

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

Research Center of Changsha Cigarette Factory, Changsha, Hunan, China

Contributions to Tobacco & Nicotine Research

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

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...

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

Published Online: Dec 30, 2014

Page range: 339 - 343

Received: Jan 15, 2001

Accepted: Jul 24, 2001

DOI: https://doi.org/10.2478/cttr-2013-0721

© 2014 Beiträge zur Tabakforschung International

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.