Sesquiterpene

A terpene built from three isoprene units, typically containing fifteen carbon atoms. Sesquiterpenes occur widely in plants, fungi, and other organisms and include both volatile compounds and components of resins.

Isoprene rule: A structural principle relating the carbon frameworks of many terpenes to linked five-carbon isoprene units. Sesquiterpenes are classified by the three isoprene units underlying their carbon skeletons.
Farnesyl pyrophosphate: A fifteen-carbon activated isoprenoid intermediate used in biosynthesis of sesquiterpenes and other molecules. Sesquiterpene synthases commonly use this three-unit precursor.
Artemisinin: A sesquiterpene lactone used as a key drug component in combination treatments for malaria. This sesquiterpene derivative demonstrates the class's direct pharmaceutical importance.
β-Caryophyllene: A bicyclic sesquiterpene found in many essential oils, including clove and black pepper oils. Its compact bicyclic skeleton is a common example of sesquiterpene structural complexity.
Terpene: A class of compounds whose carbon frameworks are assembled from isoprene-derived units. Sesquiterpene is one size-defined member of the broader terpene family.
Sesquiterpene synthase: An enzyme that converts farnesyl pyrophosphate into one or more sesquiterpene skeletons. These enzymes create much of the class's structural diversity through cyclization and rearrangement.
Humulene: A naturally occurring cyclic sesquiterpene found in hops and several aromatic plants. Its aroma and presence in hops connect sesquiterpenes to food and fragrance.
Farnesol: An acyclic sesquiterpene alcohol involved in biological signaling and present in many essential oils. Its linear skeleton contrasts with the many cyclized members of this class.
Monoterpene: A terpene typically composed of two isoprene units and ten carbon atoms. Its two-unit framework contrasts with the three-unit sesquiterpene skeleton.
Mevalonate pathway: A metabolic pathway that produces isoprenoid building blocks from acetyl-CoA. In many organisms, it supplies the precursors used to make farnesyl pyrophosphate.

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