Cubebene

Cubebenes

α-Cubebene

β-Cubebene

Names

IUPAC name

(α): (1R,5S,6R,7S,10R)-4,10-Dimethyl-7-propan-2-yltricyclo[4.4.0.0^1,5]dec-3-ene
(β): (1R,5S,6R,7S,10R)-10-Methyl-4-methylidene-7-propan-2-yltricyclo[4.4.0.0^1,5]decane

Identifiers

CAS Number

(α): 17699-14-8^Y
(β): 13744-15-5

3D model (JSmol)

(α): Interactive image
(β): Interactive image

EC Number

605-792-7

PubChem CID

(α): 42608159
(β): 93081

UNII

(α): 438H9S5RG9^Y

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-cubebene.^[3]

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.

This page was last edited on 6 June 2020, at 18:52

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References