Cubebene

Cubebenes
α-Cubebene	β-Cubebene
Names
	IUPAC name (α): (1R,5S,6R,7S,10R)-4,10-Dimethyl-7-propan-2-yltricyclo[4.4.0.01,5]dec-3-ene; (β): (1R,5S,6R,7S,10R)-10-Methyl-4-methylidene-7-propan-2-yltricyclo[4.4.0.01,5]decane;
Identifiers
CAS Number	(α): 17699-14-8 ; (β): 13744-15-5;
3D model (JSmol)	(α): Interactive image; (β): Interactive image;
ChEBI	(β): CHEBI:10363;
ChemSpider	(α): 24846711; (β): 84031;
EC Number	(α): 605-792-7; (β): 604-019-0;
KEGG	(α): C09647; (β): C09648;
PubChem CID	(α): 42608159; (β): 93081;
UNII	(α): 438H9S5RG9 ;
	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/s1 Key: XUEHVOLRMXNRKQ-PFNKYVCDSA-N;
	SMILES (α): C[C@@H]1CC[C@H]([C@H]2C13[C@@H]2C(=CC3)C)C(C)C; (β): C[C@@H]1CC[C@H]([C@H]2[C@]13[C@@H]2C(=C)CC3)C(C)C;
Properties
Chemical formula	C15H24
Molar mass	204.357 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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^[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 which is endocyclic (part of the five-membered ring) in α-cubebene, but exocyclic in β-cubeαbene.^[3]

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. ^[4]

α-cubebene was detected in Vitis vinifera Lemberger cultivar fruit via gas chromatography-mass spectrometry.^[5]

References

^ 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
^ 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.
^ 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.
^ 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.
^ 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.

[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

[EB1911-2] 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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