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Cubebene

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Cubebenes
α-Cubebene
β-Cubebene
Names
IUPAC name
  • (α): (1R,5S,6R,7S,10R)-4,10-Dimethyl-7-propan-2-yltricyclodec-3-ene
  • (β): (1R,5S,6R,7S,10R)-10-Methyl-4-methylidene-7-propan-2-yltricyclodecane
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
EC Number
  • (α): 605-792-7
  • (β): 604-019-0
KEGG
PubChem CID
UNII
InChI
  • (α): InChI=1S/C15H24/c1-9(2)12-6-5-11(4)15-8-7-10(3)13(15)14(12)15/h7,9,11-14H,5-6,8H2,1-4H3/t11-,12+,13-,14-,15?/m1/s1Key: XUEHVOLRMXNRKQ-PFNKYVCDSA-N
SMILES
  • (α): C1CC(2C132C(=CC3)C)C(C)C
  • (β): C1CC(2132C(=C)CC3)C(C)C
Properties
Chemical formula C15H24
Molar mass 204.357 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Cubebenes are a pair of chemical compounds, classified as sesquiterpenes, first isolated from Piper cubeba berries, known as cubebs.

The volatile oil 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 which is endocyclic (part of the five-membered ring) in α-cubebene, but exocyclic in β-cubeαbene.

Additional plant sources

A 2022 study detected α-cubebene in samples of oleoresin from three pine species (Pinus elliottii, Pinus pinaster, Pinus tropicalis) via mass spectrometry.

α-cubebene was detected in Vitis vinifera Lemberger cultivar fruit via gas chromatography-mass spectrometry.

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
  2.  This article incorporates text from a publication now in the public domain: Chisholm, Hugh, ed. (1911). "Cubebs". Encyclopædia Britannica. Vol. 7 (11th ed.). Cambridge University Press. p. 607.
  3. 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.
  4. 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: 102340. doi:10.1016/j.bcab.2022.102340. ISSN 1878-8181.
  5. 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)". Beilstein Journal of Organic Chemistry. 15 (1): 1945–1961. doi:10.3762/bjoc.15.190. ISSN 1860-5397. PMC 6720654. PMID 31501661.
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