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Concept
Monoterpene
Summary
Monoterpenes are a class of terpenes that consist of two isoprene units and have the molecular formula C10H16. Monoterpenes may be linear (acyclic) or contain rings (monocyclic and bicyclic). Modified terpenes, such as those containing oxygen functionality or missing a methyl group, are called monoterpenoids. Monoterpenes and monoterpenoids are diverse. They have relevance to the pharmaceutical, cosmetic, agricultural, and food industries.
Terpene#Biosynthesis
Monoterpenes are derived biosynthetically from units of isopentenyl pyrophosphate, which is formed from acetyl-CoA via the intermediacy of mevalonic acid in the HMG-CoA reductase pathway. An alternative, unrelated biosynthesis pathway of IPP is known in some bacterial groups and the plastids of plants, the so-called MEP-(2-methyl-D-erythritol-4-phosphate) pathway, which is initiated from C5 sugars. In both pathways, IPP is isomerized to DMAPP by the enzyme isopentenyl pyrophosphate isomerase.
Geranyl pyrophosphate is the precursor to monoterpenes (and hence monoterpenoids).
Elimination of the pyrophosphate group from geranyl pyrophosphate leads to the formation of acyclic monoterpenes such as ocimene and the myrcenes. Hydrolysis of the phosphate groups leads to the prototypical acyclic monoterpenoid geraniol. Additional rearrangements and oxidations provide compounds such as citral, citronellal, citronellol, linalool, and many others. Many monoterpenes found in marine organisms are halogenated, such as halomon.
Myrcen.png|[[Myrcene]] is an acyclic monoterpene, an [[alkene]] [[hydrocarbon]]
Menthol_skeletal.svg|[[Menthol]] is a monocyclic monoterpenoid
Limonene-2D-skeletal.svg|[[Limonene]] is a monocyclic monoterpene
Carvone.svg|[[Carvone]] is a monoterpenoid
Beta-thujaplicin.png|[[Hinokitiol]] is a monoterpenoid, a [[tropolone]] derivative
Linalool_skeletal.svg|[[Linalool]] is an acyclic monoterpenoid
Bicyclic monoterpenes include carene, sabinene, camphene, and thujene. Camphor, borneol, eucalyptol and ascaridole are examples of bicyclic monoterpenoids containing ketone, alcohol, ether, and bridging peroxide functional groups, respectively.
Official source
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