Cubebenes are a pair of chemical compounds, classified as

sesquiterpene Sesquiterpenes are a class of terpenes that consist of three isoprene units and often have the molecular formula C15H24. Like monoterpenes, sesquiterpenes may be cyclic or contain rings, including many combinations. Biochemical modifications s ...

s, first isolated from ''

Piper cubeba ''Piper cubeba'', cubeb or tailed pepper is a plant in genus '' Piper'', cultivated for its fruit and essential oil. It is mostly grown in Java and Sumatra, hence sometimes called Java pepper. The fruits are gathered before they are ripe, and c ...

'' berries, known as cubebs. The

volatile oil An essential oil is a concentrated hydrophobic liquid containing volatile (easily evaporated at normal temperatures) chemical compounds from plants. Essential oils are also known as volatile oils, ethereal oils, aetheroleum, or simply as the o ...

from the distillation of cubebs is a pale green or blue-yellow viscous liquid with a warm woody, slightly camphoraceous odor consisting of cubebene which comes in two forms, α- and β-cubebene, both with the molecular formula C₁₅H₂₄. They differ only in the position of a

double bond In chemistry, a double bond is a covalent bond between two atoms involving four bonding electrons as opposed to two in a single bond. Double bonds occur most commonly between two carbon atoms, for example in alkenes. Many double bonds exist betw ...

which is endocyclic (part of the five-membered ring) in α-cubebene, but

exocyclic In organic chemistry, an alicyclic compound contains one or more all-carbon rings which may be either saturated or unsaturated, but do not have aromatic character. Alicyclic compounds may have one or more aliphatic side chains attached. Cyc ...

in β-cubeαbene.

Additional plant sources

A 2022 study detected α-cubebene in samples of

oleoresin Oleoresins are semi-solid extracts composed of resin and essential or fatty oil, obtained by evaporation of the solvents used for their production. The oleoresin of conifers is known as crude turpentine or gum turpentine, which consists of oil o ...

from three pine species (

Pinus elliottii ''Pinus elliottii'', commonly known as slash pine,Family, P. P. (1990). Pinus elliottii Engelm. slash pine. ''Silvics of North America: Conifers'', (654), 338. is a conifer tree native to the Southeastern United States. Slash pine is named after ...

Pinus pinaster ''Pinus pinaster'', the maritime pine or cluster pine, is a pine native to the south Atlantic Europe region and parts of the western Mediterranean. It is a hard, fast growing pine bearing small seeds with large wings. Description ''Pinus pinast ...

, Pinus tropicalis) via

mass spectrometry Mass spectrometry (MS) is an analytical technique that is used to measure the mass-to-charge ratio of ions. The results are presented as a ''mass spectrum'', a plot of intensity as a function of the mass-to-charge ratio. Mass spectrometry is used ...

. α-cubebene was detected in

Vitis vinifera ''Vitis vinifera'', the common grape vine, is a species of flowering plant, native to the Mediterranean Basin, Mediterranean region, Central Europe, and southwestern Asia, from Morocco and Portugal north to southern Germany and east to northern ...

Lemberger cultivar fruit via gas chromatography-mass spectrometry.

References

{{reflist Sesquiterpenes Isopropyl compounds Tricyclic compounds