Muurolenes

Sampling time 60 min extraction temperature 80°C. Monoterpenes a-pinene, p-myrcene, a-phellandreneand limonene sesquiterpenes a-cubebene, a-copaene, p-elemene, p-caryophyllene, a-humulene, y-muurolene, p-eudesmene and caryophyllene oxide diterpenes cembrene A and isoincensole acetate. 

Fig. 5-3. Examples of mono- and sesquiterpenes and their derivatives in softwood. 1, a-Pinene 2, /3-pinene 3, 3-carene 4, camphene 5, borneol (R = H), bornyl acetate (R = COCH3) 6, limonene 7, a-terpineol 8, dipentene 9, a-muurolene 10, 8-cadinene 11, a-cadinol 12, a-cedrene 13, longifolene 14, juniperol.

Decarboxylation methods failed. After several trials, excess phenylmagnesium bromide was used to form the tertiary alcohol, 459, which was treated with acetic anhydride containing a trace of sulfuric acid yielding the tetrasubstituted olefin, 460 (Scheme 56). This olefin was cleaved with ruthenium tetroxide and periodate. The resulting benzophenone was radioactive, thus the pathway to muurolene proceeds via cyclodecadiene as intermediate. 

Previous studies (Z) showed evidence for the presence of at least 20 sesquKerpene hydrocarbons in pineapple. These researchers identified 7 sesquiterpenes (1 tentative). We confirmed the presence of 3 of the sesquiterpenes and identified p-copaene, y-muurolene, a- and p-selinene in addition. Mass spectral data indicated the presence of other sesquiterpene hydrocarbons and oxygenated sesquiterpenes which we have been unable to characterize at present. 

---