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
3D model (JSmol)
EC Number
  • 605-792-7
UNII
  • (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
  • (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
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

  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.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.