A Thujone

Thujane-type monoterpenes, unusual monoterpenes with a cyclopropane ring in a bicyclo[3.1.0] skeleton, are formed from the terpinen-4-yl cation directly or via the sabinyl cation. Important members include a-thujene 52, sa-binene 53, the cis isomer 54 of sabinene hydrate, sabinol 55, sabinylacetate 56, a-thujone 57, -thujone 58 and isothujanol 59 (Structure 4.13). 

Common mugwort Artemisia vulgaris L. a-Thujone (56), 1,8-cineole (27), camphor (20), borneol (19), sabinene (16)... 

Sage, Dalmatian Salvia officinalis L. a-Thujone (18-43), -thujone (3-9), 18-cineole (6-13), camphor (3-9)... 

The aldehyde citral displayed moderate activity [49-52]. Ketones such as pu-legone [53-56], fenchone [39, 57], a-thujone [58] and camphor [48-67] were reported to have antimicrobial activities. 

Isoborneol has been found to be an interesting compound for inhibiting HSV life cycle, on the basis of the specificity of the inhibition of the glycosilation of viral polyptides [137]. Also linalool exhibited the strongest activity against adenoviruses however, carvone, cineole, -caryophyllene, farnesol, fenchone, geraniol, -myrcene and a-thujone did not exhibit activity [135]. 

Apart from (-)-a-thujone (1), other stereoisomers such as (+)-(i-thujone (2) and reduced derivatives like 3-neoisothujanol (3) can be isolated from appropriate extracts of wormwood, arbor vitae, and sage. An oil derived from leaves of the red cedar Thai in plicata Don contains 8(MW (-)-a-thujone <1).1... 

Thujane monoterpenes are based on the bicyclic (G3 C5) monoterpene thujane and include umbellone (thujan-2-one) and the neuroactives a-thujone and 3-thujone (thujan-3-one isomers) that can cause convulsions. Thujones are GABA(A) receptor antagonists and are the active constituents in oil of wormwood from Artemisia absinthium (Asteraceae) used in the alcoholic drink absinthe that was eventually banned because of its deleterious neurotoxic effects. 

PROP Constituent is d-a-thujone, found in leaves of Thu/a occidentalis L. (Fam. Cupressaaceae) (FCTXAV 12,807,74). Yellowish, volatile oil strong sage odor. D 0.910-0.920. Sol in fixed oils, mineral oil, propylene glycol insol in glycerin. 

Characteristics Light yellow to yellow liquid with a thujone-like taste and odour. 

Benjilali et al. detected six chemotypes in A. herba-alba (a-thujone, p-thujone, camphor, davanone, cis-chrysanthenyl acetate and chrysanthenone type), which also differed in their geographical origin [170, 171 [. For the latest literature see [172[. 

Oppolzer et al. have utilized the above methodology to synthesize enantiomerically pure (-)a-thujone, using dimethylzinc as the anion capture agent. ... 

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