Deodarone Isomers in Cedrus atlantica Essential Oils and Tar Oils

Abstract

Deodarone [2,2,6-trimethyl-6-(4-methylcyclohex-3-enyl)-tetrahydro-4-pyrone] is a sesquiterpene tetrahydro-γ-pyrone related to bisabolene and atlantone, first isolated from Cedrus deodora essential oil. With respect to the stereochemistry of the asymmetric carbons C4 and C8, two diastereoisomers may be distinguished. Identification and quantification of both diastereoisomers in wood and tar oils from C. atlantica has been achieved using 13C NMR spectroscopy, in combination with GC (polar column). The contents of (4 R.8 R)- and (4 R.8 S)-deodarone varied between 1.1–2.8% and 1.0–3.0%, respectively.