# Cubebene

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**Cubebenes** are a pair of chemical compounds, classified as [sesquiterpenes](/source/Sesquiterpene), first isolated from *[Piper cubeba](/source/Piper_cubeba)* berries, known as cubebs.

The [volatile oil](/source/Volatile_oil) from the distillation of cubebs is a pale green or blue-yellow viscous liquid with a warm woody, slightly camphoraceous odor[1] consisting of cubebene which comes in two forms, α- and β-cubebene, both with the molecular formula C15H24.[2] They differ only in the position of a [double bond](/source/Double_bond) which is endocyclic (part of the five-membered ring) in α-cubebene, but [exocyclic](/source/Exocyclic) in β-cubeαbene.[3]

## Additional plant sources

A 2022 study detected α-cubebene in samples of [oleoresin](/source/Oleoresin) from three pine species ([Pinus elliottii](/source/Pinus_elliottii), [Pinus pinaster](/source/Pinus_pinaster), [Pinus tropicalis](/source/Pinus_tropicalis)) via [mass spectrometry](/source/Mass_spectrometry).[4]

α-cubebene was detected in [Vitis vinifera](/source/Vitis_vinifera) [Lemberger](/source/Lemberger_(grape)) cultivar fruit via [gas chromatography-mass spectrometry.](/source/Gas_chromatography%E2%80%93mass_spectrometry)[5]

## References

1. Lawless, Julia (1995), *The Illustrated Encyclopedia of Essential Oils: The Complete Guide to the Use of Oils in Aromatherapy and Herbalism*, Element Books, ISBN 978-1-85230-721-9

1. Ohta, Yoshimoto; Sakai, Tsutomu; Hirose, Toshio (1966). "Sesquiterpene hydrocarbons from the oil of cubeb α-cubebene and β-cubebene". *Tetrahedron Letters*. **7** (51): 6365–6370. [doi:10.1016/S0040-4039(00)70179-1](https://doi.org/10.1016/S0040-4039(00)70179-1)

1. Rubini, Morandise; Clopeau, Armand; Sandak, Jakub; Dumarcay, Stephane; Sandak, Anna; Gerardin, Philippe; Charrier, Bertrand (2022-07-01). "Characterization and classification of Pinus oleoresin samples according to Pinus species, tapping method, and geographical origin based on chemical composition and chemometrics". *Biocatalysis and Agricultural Biotechnology*. **42**. [doi:10.1016/j.bcab.2022.102340](https://doi.org/10.1016/j.bcab.2022.102340). [ISSN 1878-8181](https://www.worldcat.org/issn/1878-8181)

1. Könen, Philipp P. & Wüst, Matthias (2019-08-14). ["Analysis of sesquiterpene hydrocarbons in grape berry exocarp (Vitis vinifera L.) using in vivo-labeling and comprehensive two-dimensional gas chromatography–mass spectrometry (GC×GC–MS)"](https://www.beilstein-journals.org/bjoc/articles/15/190). *Beilstein Journal of Organic Chemistry*. **15** (1): 1945–1961. [doi:10.3762/bjoc.15.190](https://doi.org/10.3762/bjoc.15.190). [ISSN 1860-5397](https://www.worldcat.org/issn/1860-5397). [PMC 6720654](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6720654). [PMID 31501661](https://pubmed.ncbi.nlm.nih.gov/31501661)

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Adapted from the Wikipedia article [Cubebene](https://en.wikipedia.org/wiki/Cubebene) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Cubebene?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.