Y-Cadinene

The volatile extract obtained from galbanum was principally composed of a-pinene (1), p-pinene (4), fenchyl acetate (30), y-cadinene (66), guaiol (77) and <7,v-guai-9-en-1 l-ol... 

Six male specific compounds were isolated from the crucifer flea beetle, Phyllotreta cruciferae, and the same compounds plus two additional compounds were isolated from males of Aphthona flava, A. czwalinae, and A. cyparissiae. Three of the compounds were identified as (-F)-i r-himachalene, (-F)- ra w-a-himachalene (-F)-y-cadinene. Two other compounds were identified as new enantiomers of himachalene hydrocarbons that were previously identified from the fir trees, Abies alba and Abies nordmanniana. Finally, there were two himachalene alcohols and one nonsesquiterpene ketone that is a himachalene analog that were identified. The chemical and electrophysiological patterns are consistent with, but do not prove, a pheromonal function. 

Cadinene is a trivial name of a number of isomers which occur in a wide variety of essential oils e.g. cubeb oil. Actually, it is derived from the Cade juniper Juniperus oxycedrus L.). The cadalane (4-isopropyl-1,6-dimethyldecahydro-naphthalene) carbon skeleton is the base. Prominent stereochemical isomers are a-cadinene 79, y-cadinene 80 and d-cadinene 81 (Structure 4.23). This group is also known as naphthalene-type sesquiterpenes. 

Terpenes a-Copane, a-terpineol, guaiene, valencene, 8-cadinene, y-cadinene... 

The fungal metabolite avocettin (23) may be derived from antipodal y-cadinene (22) by three plausible routes (Scheme 4). Feeding of [2- C]MVA in... 

Figure 3. Ginger 1 - 1.8-cineole, 2 - oc-terpinolene, 3 - zingiberene, 4 - P-bisabolene, 5 - y-cadinene, 6 -P-sesquiterpene.

Fig. 21.9. Proposed mechanism for the conversion of. F-famesyl pyrophosphate to y-cadinene.

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