Thujopsene

Thujopsene
Names
IUPAC name
(1aS,4aS,8aS)-2,4a,8,8-Tetramethyl-1,1a,4,4a,5,6,7,8-octahydrocyclopropa[d]naphthalene
Other names
Sesquichamene; Thujopsen; Widdrene
Identifiers
470-40-6
ChemSpider 390845
Jmol interactive 3D Image
PubChem 442402
Properties
C15H24
Molar mass 204.36 g·mol−1
Density 0.936 g/mL (20 °C)[1]
Boiling point 258 to 260 °C (496 to 500 °F; 531 to 533 K)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Thujopsene is a natural chemical compound, classified as a sesquiterpene, with the molecular formula C15H24.

Thujopsene is found in the essential oil of a variety of conifers,[2] in particular Juniperus cedrus and Thujopsis dolabrata in which it comprises around 2.2% of the weight of the heartwood.[3]

Biosynthesis

Thujopsene is biosynthesized from farnesyl pyrophosphate (FPP):[4]

References

  1. 1 2 "(−)-Thujopsene". Sigma-Aldrich.
  2. Erdtman, H.; Norin, T. (1960). "Structure of thujopsene and hinokiic acid from coniferous wood". Chemistry and Industry (22): 622–623.
  3. Runeburg, Jarl; Gramstad, Thor; Larsson, Lennart; Dodson, R. M. (1960). "The Chemistry of the Natural Order Cupressales XXX. Constituents of Juniperus cedrus L.". Acta Chemica Scandinavica 14: 1991–1994. doi:10.3891/acta.chem.scand.14-1991.
  4. J. Mann; et al. Natural Products: their chemistry and biological significance. ISBN 978-0582060098.
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