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Terpene

physical science Maturity 5-7 Next article →

Terpenes are a massive and highly diverse class of natural products. They are unsaturated hydrocarbons, which means they are molecules made of carbon and hydrogen with specific chemical bonds. Scientists estimate there are about 55,000 different chemical entities in the terpene and terpenoid families.

Résine
Résine

While they are found in many organisms, they are produced predominantly by plants, especially conifers. Terpenes serve as essential biosynthetic building blocks for many life forms. For instance, steroids are actually derivatives of a triterpene called squalene. Because of their wide range of uses, they are vital to both nature and human industry.

The way these molecules are built follows the biogenetic isoprene rule. This rule describes how small units called isoprene (C5H8) link together to form larger structures.

Synthesis of geranyl pyrophosphate
Synthesis of geranyl pyrophosphate

These units are provided to the organism in two specific forms: isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP). These two building blocks are produced through two different metabolic pathways. The mevalonate (MVA) pathway is used by most archaea, animals, and fungi. The non-mevalonate (MEP) pathway starts with pyruvate and glyceraldehyde 3-phosphate (G3P) and is used mostly by bacteria. Some plants, like green algae and land plants, can use both pathways.

Building a complex terpene is a step-by-step assembly process. First, the enzyme isopentenyl pyrophosphate isomerase converts IPP into DMAPP. These two units then condense to create geranyl pyrophosphate (GPP).

TerpeneVterpenoid
TerpeneVterpenoid

GPP is the essential precursor for all monoterpenes. From this stage, the molecule can be converted into even larger structures. For example, it can become farnesyl pyrophosphate (FPP), which is the precursor for sesquiterpenes. It can also become geranylgeranyl pyrophosphate (GGPP), which leads to diterpenes. This process is mediated by enzymes known as terpene synthases.

Chemists classify terpenes based on the number of carbon atoms they contain. This classification uses specific prefixes to show how many isoprene units are present. Monoterpenes consist of two isoprene units and have the formula C10H16. Sesquiterpenes contain 15 carbons (C15H24), while diterpenes contain 20 carbons (C20H32).

Naturkautschuk
Naturkautschuk

There are also tetraterpenes, which use eight isoprene units and form the carotenoids. While terpenes are pure hydrocarbons, terpenoids are modified versions. Terpenoids contain additional functional groups, which are usually oxygen-containing. Although the terms are often used interchangeably, they describe slightly different chemical states.

The history of studying these compounds is quite rich. In 1866, the German chemist August Kekulé coined the term "Terpen." He wanted to reduce confusion because many different hydrocarbons were all being called "camphene." The name is a shortened version of the German word for turpentine, "Terpentin." Later, the field reached a major milestone in 1939. Leopold Ružička was awarded the Nobel Prize in Chemistry for his work on higher terpenes. His research included the first chemical synthesis of male sex hormones.

Terpenes have many important roles in the natural world. In plants, they act as mediators for ecological interactions. They can help plants defend themselves against diseases or animals that try to eat them. Some terpenes even help plants attract pollinators or communicate with other plants.

Osmeterium
Osmeterium

In warmer weather, trees release higher amounts of terpenes into the air. This may act as a natural mechanism for cloud seeding. The resulting clouds reflect sunlight, which helps regulate the temperature of the forest. Even insects use them; certain termites eject a resinous mixture of terpenes to ward off predators.

Humans use terpenes in a wide variety of commercial applications. One major example is natural rubber, known as polyisoprene. Turpentine, a mixture of terpenes like alpha-pinene, is used as an organic solvent.

IndustrialRouteGeranylAlc
IndustrialRouteGeranylAlc

Another product, rosin, is used in inks, varnishes, and adhesives. It is even used by ballet dancers for traction and baseball pitchers for better control. Many terpenes provide the pleasant scents and flavors in perfumes, cosmetics, and foods like hops. Finally, because they reflect plant defenses, they are used as active ingredients in agricultural pesticides and traditional aromatherapy.

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🖼️ Images & Media (7)
File:Résine.jpg
Résine.jpg
File:Naturkautschuk.svg
Naturkautschuk.svg
File:Tetrahydrocannabinol.svg
Tetrahydrocannabinol.svg
File:TerpeneVterpenoid.svg
TerpeneVterpenoid.svg
File:Synthesis of geranyl pyrophosphate.png
Synthesis of geranyl pyrophosphate.png
File:Osmeterium.JPG
Osmeterium.JPG
File:IndustrialRouteGeranylAlc.png
IndustrialRouteGeranylAlc.png
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