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 13 C 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.

Comparative Chemical and Biological Analysis of Wood and Tar Essential Oils from Cedrus atlantica and Juniperus oxycedrus in Morocco

“…Analyzing Juniperus oxycedrus essential oil samples unveiled eleven Numerous studies have delved into the composition of cedar essential oil, revealing a distinct array of molecules. These include (α, β, γ) himachalane, 29,32,37,39,47,71,73 cedrol, 39 isocedranol, 39,47 himachalol, 47,69 I-epicubenol, 47 α-pinene, 39,69 Zα-Atlantone, 47,70 E-γ-Atlantone, 70 E-α-Atlantone, 32,37,47,70,71,73 5-isocedrano, 70 9-iso-thujopsanone, 70 cedranone, 70 8-Cedren-13-ol, 37 cedroxide, 37 deodarone, 37,47,74 α-cedrene, 75 β-cedrene, 75 isovanillincamphor, 75 β-caryophyllene , 69,75 caryophyllene oxide, 69,75 p-cresol, 75 α-humulene, 69 and guaiacol. 75 In a Slovakian study, the primary constituents in commercially available cedar essential oil were identified as δ-cadinene, (Z)-βfarnesene, β-himachalene, viridi-florol, and himachala-2,4-diene.…”

Chemical Characterization and Antioxidant Activity of Cedrus atlantica Manetti Tar (Atlas Cedar Tar)

“…Despite all these traditional uses, the extract was not properly evaluated (few studies have been devoted to these products [4,5,7,9]) especially the Cedrus atlantica Manetti tar whose researches focuses mainly on essential oils of wood and oil tar of this specie [10,11,12,13,3,14,15].…”