FIGURE 5.24 Some sesquiterpenoid alcohols.

FIGURE 5.25 Some sesquiterpenoid hydrocarbons.

Vetiver and patchouli are two oils of great importance in perfumery (Williams, 1996, 2004). Both contain complex mixtures of sesquiterpenoids, mostly with complex polycyclic structures (Sell, 2003). The major components of vetiver oil are a-vetivone (136), b-vetivone (137), and khusimol (119), but the most important components as far as odor is concerned are minor constituents such as khusimone (151), zizanal (152), and methyl zizanoate (153). Nootkatone (154) is an isomer of a-vetivone and is an important odor component of grapefruit. Patchouli alcohol (145) is the major constituent of patchouli oil but, as is the case also with vetiver, minor components are more important for the odor profile. These include nor-patchoulenol (155) and nor-tetrapatchoulol (156) (Figure 5.26).

The molecules of chamazulene (150), khusimone (151), nor-patchoulenol (155), and nor-tetrapatchoulol (156) each contain only 14 carbon atoms in place of the normal 15 of sesquiterpenoids. They are all degradation products of sesquiterpenoids. Degradation, either by enzymic action or from environmental chemical processes, can be an important factor in generating essential oil components. Carotenoids are a family of tetraterpenoids characterized by having a tail-to-tail fusion between two diterpenoid fragments. In the case of b-carotene (157), both ends of the chain have been cyclized to form cyclohexane rings. Degradation of the central part of the chain leads to a number of fragments that are found in essential oils and the two major families of such are the ionones and damascones. Both have the same carbon skeleton but in the ionones (Leffingwell & Associates, n.d.;

154 155

FIGURE 5.26 Components of vetiver, patchouli, and grapefruit.

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