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Spathulenol

From Wikipedia, the free encyclopedia
Spathulenol
Names
IUPAC name
6β,11-Cyclo-4α,5β-guai-10(14)-en-4-ol
Systematic IUPAC name
(1aR,4aR,7S,7aR,7bR)-1,1,7-Trimethyl-4-methylidenedecahydro-1H-cyclopropa[e]azulen-7-ol
Other names
Spatulenol
Identifiers
3D model (JSmol)
UNII
  • C[C@@]1(CC[C@@H]2[C@@H]1[C@H]3[C@H](C3(C)C)CCC2=C)O
Properties
C15H24O
Molar mass 220.356 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Spathulenol is a tricyclic sesquiterpene alcohol which has a basic skeleton similar to the azulenes. It occurs in oregano among other plants.

History and occurrence

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A volatile oil was extracted from waterwort distillery (Artemisia vulgaris) and tarragon (Artemisia dracunculus), from which the sesquiterpene alcohol spathulenol was isolated for the first time in 1975 as a colorless, viscous compound with an earth-aromatic odor and bitter-spicy taste.[1]

References

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  1. ^ Juell, S. Monrad-Krohn; Hansen, Rudolf; Jork, Hellmut (1976). "Neue Substanzen aus ätherischen Ölen verschiedener Artemisia-Species, 1. Mitt.: Spathulenol, ein azulenogener Sesquiterpenalkohol". Archiv der Pharmazie. 309 (6): 458–466. doi:10.1002/ardp.19763090605. PMID 962558. S2CID 95354157.