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
CAS Number	470-40-6
ChemSpider	390845
Jmol interactive 3D	Image
PubChem	442402
InChI InChI=1S/C15H24/c1-11-6-9-14(4)8-5-7-13(2,3)15(14)10-12(11)15/h6,12H,5,7-10H2,1-4H3/t12-,14-,15-/m0/s1 Key: WXQGPFZDVCRBME-QEJZJMRPSA-N InChI=1/C15H24/c1-11-6-9-14(4)8-5-7-13(2,3)15(14)10-12(11)15/h6,12H,5,7-10H2,1-4H3/t12-,14-,15-/m0/s1 Key: WXQGPFZDVCRBME-QEJZJMRPBP
SMILES C\2=C(\[C@H]3[C@@]1([C@](CCCC1(C)C)(C)C/2)C3)C
Properties
Chemical formula	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. "(−)-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.