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Δ-Cadinol

1-epi-α-Cadinol 1β-Cadin-4-en-10-ol

δ-Cadinol is an organic compound, a sesquiterpenoid alcohol produced by many plants as well as some animals and microorganisms. It is a white crystalline solid, soluble in isopropyl ether and ethanol. It is an epimer of α-cadinol.

δ-Cadinol exists in nature as either of two enantiomers distinguished by the prefixes (+)- and (−)-. The (+)-isomer was identified by E. Shinozaki in 1922 from the leaves of Torreya nucifera and originally named torreyol. Lambertol is thought to be either (+)-δ-cadinol or (−)-δ-cadinol.

Occurrence

δ-Cadinol is produced by the fungus Xylobolus frustulatus as long white needles when grown in malt agar medium. It also occurs in many conifers, and in many other organisms including

  • Achillea millefolium (6%)
  • Cedrela odorata
  • Clitocybe illudens (a mushroom)
  • Copaifera multijuga (1%; a major contributor to the aroma of copaiba oil)
  • Dictyopteris divaricata (a brown alga)
  • Plebejus argyrognomon (a butterfly; acts as a pheromone)

References

References

  1. (1966). "(---)-Torreyol ("delta-Cadinol")". Acta Chemica Scandinavica.
  2. Lars Westfelt (1970), "(−)-Torryeol ('δ-Cadinol')". ''Acta Chemica Scandinavica'' volume 24 issue 5 16181622 {{doi. 10.3891/acta.chem.scand.24-1618
  3. (1981). "Configurations and conformations of torreyol (δ-cadinol), α-cadinol, T-muurolol and T-cadinol". Tetrahedron.
  4. (1967). "Structure et configuration absolue du cédrélanol ((−)-δ-cadinol), alcool sesquiterpénique C15H26O l'huile essentielle ''Cedrela odorata brasiliensis''". Canadian Journal of Chemistry.
  5. (1984). "Isolation and identification of the sesquiterpenoid (+)-torreyol fromXylobolus frustulatus". Experimental Mycology.
  6. (2010). "Antibacterial activities of essential oils and extracts of TurkishAchillea, SaturejaandThymusspecies against plant pathogenic bacteria". Journal of the Science of Food and Agriculture.
  7. (2007). "Characterization of woody odorant contributors in copaiba oil (Copaifera multijuga Hayne)". Journal of the Brazilian Chemical Society.
  8. (1976). "Wing scents and scent-released phases in the courtship behavior of Lycaeides argyrognomon (Lepidoptera: Lycaenidae)". Journal of Chemical Ecology.
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