Sesquiterpene

Sesquiterpenes are a class of terpenes that consist of three isoprene units and have the molecular formula C15H24. Like monoterpenes, sesquiterpenes may be acyclic or contain rings, including many unique combinations. Biochemical modifications such as oxidation or rearrangement produce the related sesquiterpenoids.

Acyclic

Biosynthetically, when geranyl pyrophosphate reacts with isopentenyl pyrophosphate, the result is the 15-carbon farnesyl pyrophosphate which is an intermediate in the biosynthesis of sesquiterpenes such as farnesene. Oxidation can then provide sesquiterpenoids such as farnesol. Sesquiterpenes are found naturally in plants as defensive agents.

Monocyclic

With the increased chain length and additional double bond, the number of possible ways that cyclization can occur is also increased and there exist a wide variety of cyclic sesquiterpenes. In addition to common six-membered ring systems such as is found in zingiberene, a consitituent of the oil from ginger, cyclization of one end of the chain to the other end can lead to macrocyclic rings such as humulene.

Bicyclic

In addition to common six-membered rings such as in the cadinenes, one classic bicyclic sesquiterpene is caryophyllene, from the oil of cloves, which has a nine-membered ring and cyclobutane ring. Additional unsaturation provides aromatic bicyclic sesquiterpenoids such as vetivazulene and guaiazulene.

Tricylic

With the addition of a third ring, the possible structures become increasingly varied. Examples include longifolene, copaene and the alcohol patchoulol.


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  • Sesquiterpene — Sesquiterpène Les sesquiterpènes sont une classe de terpène formée de 3 unités isoprènes et a comme formule moléculaire C15H24. Comme les monoterpènes, une molécule de sesquiterpène peut être acyclique ou contenir 1 a 2 cycles (comme le… …   Wikipédia en Français

  • sesquiterpène — [ sɛskɥitɛrpɛn ] n. m. • 1886; de sesqui « une fois et demie » et terpène ♦ Chim. Terpène aliphatique ou cyclique, formé de trois unités d isoprène (C15H24). Les sesquiterpènes sont les plus abondants parmi les terpènes. ● sesquiterpène nom… …   Encyclopédie Universelle

  • Sesquiterpene — Struktur von Isopren Die Terpene sind eine stark heterogene und sehr große Gruppe von chemischen Verbindungen, welche als sekundäre Inhaltsstoffe in Organismen natürlich vorkommen. Sie zeichnen sich durch eine große Vielfalt an… …   Deutsch Wikipedia

  • Sesquiterpène — Les sesquiterpènes sont une classe de terpène formée de 3 unités isoprènes et a comme formule moléculaire C15H24. Comme les monoterpènes, une molécule de sesquiterpène peut être acyclique ou contenir 1 à 2 cycles (comme le polygodial), de très… …   Wikipédia en Français

  • sesquiterpene — seskviterpenas statusas T sritis chemija apibrėžtis Terpenas. formulė (C₅H₈)₃ atitikmenys: angl. sesquiterpene rus. сесквитерпен …   Chemijos terminų aiškinamasis žodynas

  • sesquiterpene — noun Date: circa 1888 any of a class of terpenes C15H24; also a derivative of such a terpene …   New Collegiate Dictionary

  • sesquiterpene — /ses kwi terr payn/, n. Chem. See under terpene. [1885 90; SESQUI + TERPENE] * * * …   Universalium

  • sesquiterpene — noun Any terpene formed from three isoprene units, and having fifteen carbon atoms; includes several plant pigments such as the flavones. See Also: sesquiterpenoid, terpene …   Wiktionary

  • sesquiterpene — ses·qui·ter·pene .ses kwi tər .pēn n any of a class of terpenes C15H24 containing half again as many atoms in each molecule as monoterpenes also a derivative of such a terpene …   Medical dictionary

  • sesquiterpene — pl.m. sesquiterpeni …   Dizionario dei sinonimi e contrari

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