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 (4R.8R)- and (4R.8S)-deodarone varied between 1.1–2.8% and 1.0–3.0%, respectively.
ShankaranarayananR., KrishnappaS., BisaryaS.C., DevS. (1973) Deodarone, a novel sesquiterpene tetrahydro-γ-pyrone from Cedrus deodora essential oil. Tetrahedron Letters, 14, 427–428.
2.
AdamsD.R., BhatnagarS.P., CooksonR.C. (1975) Structure and synthesis of a new ketone from Cedrus species; some new constituents of C. atlantica Manet. Journal of the Chemical Society, Perkin Transactions1, 1502–1506.
3.
GopichandY., ChakravartiK.K. (1974) Total synthesis of α-bisabolol-3-one and deodarone. Tetrahedron Letters, 15, 3851–3852.
4.
IsagerI.T. (1990) Reactions with alpha, beta-unsaturated nitrile oxides. Synthetic studies in the terpene field. Synthesis of tagetones, ocimenones, deodarone, and atlantone. Acta Chemica Scandinavia, 44, 806–813.
5.
VilleccoM.B., HernándezL.R., GuzmánM.I., CatalánC.A.N., BucioM.A., Joseph-NathanP. (2001) Synthesis, stereochemistry and absolute configuration of deodarols and deodarones. Tetrahedron: Asymmetry, 12, 2947–2953.
6.
(a) NigamM.C., AteequeA., MisraL.N. (1990) Composition of the essential oil of Cedrus deodara.Indian Perfumer, 34, 278–281; (b) Chalchat JC, Garry RP, Michet A, Benjilali B. (1994) Essential oil components in sawdust of Cedrus atlantica from Morocco. Journal of Essential Oil Research, 6, 323-325; (c) Aberchane M, Satrani B, Fechtal M, Chaouch A. (2003) Effet de l'infection du bois de Cèdre de l'Atlas par Trametes pini et Ungulina officinalis sur la composition chimique et l'activité antibactérienne et antifongique des huiles essentielles. Acta Botanica Gallica, 150, 223-229; (d) Aberchane M, Fechtal M, Chaouch A. (2004) Analysis of Moroccan Atlas cedarwood oil (Cedrus atlantica Manetti). Journal of Essential Oil Research, 16, 542-547; (e) Lawrence BM. (2012) Himalayan cedar wood oil. Perfumer & Flavorist, 32, 42-44.
7.
SatraniB., AberchaneM., FarahA., ChaouchA., TalbiM. (2006) Composition chimique et activité antimicrobienne des huiles essentielles extraites par hydrodistillation fractionnée du bois de Cedrus atlantica Manetti. Acta Botanica Gallica, 153, 97–104.
8.
ChaudharyA., SharmaP., NaddaG., TewaryD.K., SinghB. (2011) Chemical composition and larvicidal activities of the Himalayan Cedar, Cedrus deodara essential oil and its fractions against the diamondback moth, Plutella xylostella.Journal of Insect Science, 11, 1–10.
9.
PaoliM., NamA.M., CastolaV., CasanovaJ., BighelliA. (2011) Chemical variability of the wood essential oil of Cedrus atlantica Manetti from Corsica. Chemistry and Biodiversity, 8, 344–351.
10.
NamA.M., CasanovaJ., TomiF., BighelliA. (2014) Composition and chemical variability of Corsican Pinus halepensis cone oil. Natural Product Communications., 9, 1361–1364.
