Tabanone

Tabanone is a slightly yellow to yellow liquid with a warm, dry, sweet, and tobacco-like odor.Thesubstance is predominantly used in tobacco flavors, but also to create powdery tobacco nuances in fragrances.
The material may be produced by dehydration of 3-oxo--ionol.

Tabanone is found in oils of Trifolium pratense L. and is a potential natural antioxidant.

Not classified

Tabanon (Symrise)

1) Using -isophorone as raw material, -isophorone was obtained by acetylacetonate iron(III) isomerization, and then reacted with trimethylchlorosilane in DMF in the presence of sodium iodide catalyzed and acid-binding agent triethylamine, to obtain -isophorone trimethylsilane allyl ether, yield 45%.

2) -isophorone trimethylsilyl enol ether was reacted with crotonaldehyde by Aldol, and the product was synthesized in one step by distillation and dehydration to give nicotinone in 46% yield.

[1] FUJIMORI T, KASUGA R, KANEKO H, et al. Neutral Volatile Components of Burley Tobacco[C]//16 1. 1978: 0. DOI: 10.2478/cttr-2013-0950
[2] DAVIDE SLAGHENAUFI . Quantitative solid phase microextraction – Gas chromatography mass spectrometry analysis of five megastigmatrienone isomers in aged wine[J]. Analytica Chimica Acta, 2014, 813: Pages 63-69. DOI: 10.1016/j.aca.2014.01.019