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

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

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 det...

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Main Authors: Yang H, Liu J, Li K, Yin X, Tan X, Wang J
Format: Article
Language:English
Published: Sciendo 2001-10-01
Series:Beiträge zur Tabakforschung International
Online Access:https://doi.org/10.2478/cttr-2013-0721
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spelling doaj-c04d258f4c324658bba795c5331dd69d2021-09-06T19:22:13ZengSciendoBeiträge zur Tabakforschung International1612-92372001-10-0119733934310.2478/cttr-2013-0721cttr-2013-0721Synthesis of 3-Oxo-α-ionol Ethyl Carbonate and its Conversion to Megastigmatrienones in Tobacco SmokeYang H0Liu J1Li K2Yin X3Tan X4Wang J5Research Center of Changsha Cigarette Factory, Changsha, Hunan, ChinaResearch Center of Changsha Cigarette Factory, Changsha, Hunan, ChinaResearch Center of Changsha Cigarette Factory, Changsha, Hunan, ChinaResearch Center of Changsha Cigarette Factory, Changsha, Hunan, ChinaResearch Center of Changsha Cigarette Factory, Changsha, Hunan, ChinaResearch Center of Changsha Cigarette Factory, Changsha, Hunan, China3-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.https://doi.org/10.2478/cttr-2013-0721
collection DOAJ
language English
format Article
sources DOAJ
author Yang H
Liu J
Li K
Yin X
Tan X
Wang J
spellingShingle Yang H
Liu J
Li K
Yin X
Tan X
Wang J
Synthesis of 3-Oxo-α-ionol Ethyl Carbonate and its Conversion to Megastigmatrienones in Tobacco Smoke
Beiträge zur Tabakforschung International
author_facet Yang H
Liu J
Li K
Yin X
Tan X
Wang J
author_sort Yang H
title Synthesis of 3-Oxo-α-ionol Ethyl Carbonate and its Conversion to Megastigmatrienones in Tobacco Smoke
title_short Synthesis of 3-Oxo-α-ionol Ethyl Carbonate and its Conversion to Megastigmatrienones in Tobacco Smoke
title_full Synthesis of 3-Oxo-α-ionol Ethyl Carbonate and its Conversion to Megastigmatrienones in Tobacco Smoke
title_fullStr Synthesis of 3-Oxo-α-ionol Ethyl Carbonate and its Conversion to Megastigmatrienones in Tobacco Smoke
title_full_unstemmed Synthesis of 3-Oxo-α-ionol Ethyl Carbonate and its Conversion to Megastigmatrienones in Tobacco Smoke
title_sort synthesis of 3-oxo-α-ionol ethyl carbonate and its conversion to megastigmatrienones in tobacco smoke
publisher Sciendo
series Beiträge zur Tabakforschung International
issn 1612-9237
publishDate 2001-10-01
description 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.
url https://doi.org/10.2478/cttr-2013-0721
work_keys_str_mv AT yangh synthesisof3oxoaionolethylcarbonateanditsconversiontomegastigmatrienonesintobaccosmoke
AT liuj synthesisof3oxoaionolethylcarbonateanditsconversiontomegastigmatrienonesintobaccosmoke
AT lik synthesisof3oxoaionolethylcarbonateanditsconversiontomegastigmatrienonesintobaccosmoke
AT yinx synthesisof3oxoaionolethylcarbonateanditsconversiontomegastigmatrienonesintobaccosmoke
AT tanx synthesisof3oxoaionolethylcarbonateanditsconversiontomegastigmatrienonesintobaccosmoke
AT wangj synthesisof3oxoaionolethylcarbonateanditsconversiontomegastigmatrienonesintobaccosmoke
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