Terpene

Terpenes ( TUR-peenz) are a large and diverse class of natural products with the general formula (C5H8)n, where n ≥ 2. They serve as crucial biosynthetic building blocks in many organisms, particularly plants. Comprising more than 30,000 compounds, these unsaturated hydrocarbons are produced predominantly by plants, particularly conifers. In plants, terpenes and terpenoids are important mediators of ecological interactions, while some insects use some terpenes as a form of defense. Other functions of terpenoids include cell growth modulation and plant elongation, light harvesting and photoprotection, and membrane permeability and fluidity control. Terpenes are classified by the number of carbons: monoterpenes (C10), sesquiterpenes (C15), diterpenes (C20), as examples. The terpene alpha-pinene is a major component of turpentine, a common solvent. One terpene that has major applications is natural rubber (i.e., polyisoprene). The possibility that other terpenes could be used as precursors to produce synthetic polymers has been investigated. Many terpenes have been shown to have pharmacological effects. Terpenes are also components of some traditional medicines, such as aromatherapy, and as active ingredients of pesticides in agriculture.

History and terminology The term Terpen (German) was coined in 1866 by the German chemist August Kekulé to denote all hydrocarbons having the empirical formula C10H16, of which camphene was one. Previously, many hydrocarbons having the empirical formula C10H16 had been called "camphene", but many other hydrocarbons of the same composition had different names. Kekulé coined the term "Terpen" in order to reduce the confusion. The name is a shortened form of "Terpentin", the german word for "turpentine". Although sometimes used interchangeably with "terpenes", terpenoids (or isoprenoids) are modified terpenes that contain additional functional groups, usually oxygen-containing. The terms terpenes and terpenoids are often used interchangeably, however. Furthermore, terpenes are produced from terpenoids and many terpenoids are produced from terpenes. Both have strong and often pleasant odors, which may protect their hosts or attract pollinators. The number of terpenes and terpenoids is estimated at 55,000 chemical entities. The 1939 Nobel Prize in Chemistry was awarded to Leopold Ružička "for his work on polymethylenes and higher terpenes", "including the first chemical synthesis of male sex hormones."

Biological function Terpenes are major biosynthetic building blocks. Steroids, for example, are derivatives of the triterpene squalene. Terpenes and terpenoids are also the primary constituents of the essential oils of many types of plants and flowers. In plants, terpenes and terpenoids are important mediators of ecological interactions. For example, they play a role in plant defense against herbivory, disease resistance, attraction of mutualists such as pollinators, as well as potentially plant-plant communication. They appear to play roles as antifeedants. Other functions of terpenoids include cell growth modulation and plant elongation, light harvesting and photoprotection, and membrane permeability and fluidity control. Higher amounts of terpenes are released by trees in warmer weather, where they may function as a natural mechanism of cloud seeding. The clouds reflect sunlight, allowing the forest temperature to regulate. Some insects use some terpenes as a form of defense. For example, termites of the subfamily Nasutitermitinae ward off predatory insects through the use of a specialized mechanism called a fontanellar gun, which ejects a resinous mixture of terpenes.

Applications

One terpene that has major applications is natural rubber (i.e., polyisoprene). The possibility that other terpenes could be used as precursors to produce synthetic polymers has been investigated as an alternative to the use of petroleum-based feedstocks. However, few of these applications have been commercialized. Many other terpenes, however, have smaller scale commercial and industrial applications. For example, turpentine, a mixture of terpenes (e.g., pinene), obtained from the distillation of pine tree resin, is used as an organic solvent and as a chemical feedstock (mainly for the production of other terpenoids). Rosin, another by-product of conifer tree resin, is widely used as an ingredient in a variety of industrial products, such as inks, varnishes and adhesives. Rosin is also used by violinists (and players of similar bowed instruments) to increase friction on the bow hair, by ballet dancers on the soles of their shoes to maintain traction on the floor, by gymnasts to keep their grips while performing, and by baseball pitchers to improve their control of the baseball. Terpenes are widely used as fragrances and flavors in consumer products such as perfumes, cosmetics and cleaning products, as well as food and drink products. For example, the aroma and flavor of hops comes, in part, from sesquiterpenes (mainly α-humulene and β-caryophyllene), which affect beer quality. Some form hydroperoxides that are valued as catalysts in the production of polymers. Many terpenes have been shown to have pharmacological effects, although most studies are from laboratory research, and clinical research in humans is preliminary. Terpenes are also components of some traditional medicines, such as aromatherapy. Reflecting their defensive role in plants, terpenes are used as active ingredients of pesticides in agriculture.

Physical and chemical properties Terpenes are colorless, although impure samples are often yellow. Boiling points scale with molecular size: terpenes, sesquiterpenes, and diterpenes respectively at 110, 160, and 220 °C. Being highly non-polar, they are insoluble in water. Being hydrocarbons, they are highly flammable and have low specific gravity (float on water). They are tactilely light oils considerably less viscous than familiar vegetable oils like corn oil (28 cP), with viscosity ranging from 1 cP (à la water) to 6 cP. Terpenes are local irritants and can cause gastrointestinal disturbances if ingested. Terpenoids (mono-, sesqui-, di-, etc.) have similar physical properties but tend to be more polar and hence slightly more soluble in water and somewhat less volatile than their terpene analogues. Highly polar derivatives of terpenoids are the glycosides, which are linked to sugars. These are water-soluble solids.

Biosynthesis

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