The Journal of Organic Chemistry

The Structure, Chemistry, and Synthesis of Solanone. A New Anomalous Terpenoid Ketone from Tobacco1

RR Johnson, JA Nicholson

Index: Johnson,R.R.; Nicholson,J.A. Journal of Organic Chemistry, 1965 , vol. 30, p. 2918 - 2921

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Citation Number: 37

Abstract

A new 13-carbon ketone, solanone, has been isolated in 0.0036% yield from tobacco and identified as L-(+)-2-methyl-5-isopropyl-l, 3-nonadien-8-one. Solanone is stable under basic conditions, but rearranges in acid to the geometrical isomers of 2-methyl-5-isopropyl-2, 4- nonadien-8-one, isosolanone-A and isosolanone-B. Air oxidation of solanone proceeds through a nonvolatile intermediate to form 5-isopropyl-3-nonene-2, 8-dione which has ...