Δ-Cadinol Explained

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 (−)-.^{[1] [2]} The (+)-isomer was identified by E. Shinozaki in 1922 from the leaves of Torreya nucifera and originally named torreyol.^[1] The (−)-isomer was isolated in 1951 by Haagen-Smit and others from Pinus albicaulus and first called albicaulol.^[1] Its structure was determined in 1970 by Lars Westfelt.^[2] Other names were given to δ-cadinol based on its various biological sources before the structures were confirmed, including sesquigoyol for (+)-δ-cadinol and pilgerol for (−)-δ-cadinol.^{[2] [3]} Lambertol is thought to be either (+)-δ-cadinol or (−)-δ-cadinol.^[2] Cedrelanol was originally thought to be identical to (−)-δ-cadinol but was later confirmed to have the structure of τ-cadinol.^[4]

Occurrence

δ-Cadinol is produced by the fungus Xylobolus frustulatus as long white needles when grown in malt agar medium.^[5] It also occurs in many conifers,^[1] and in many other organisms including

• Achillea millefolium (6%)^[6]
• Cedrela odorata^[1]
• Clitocybe illudens (a mushroom)^[3]
• Copaifera multijuga (1%; a major contributor to the aroma of copaiba oil)^[7]
• Dictyopteris divaricata (a brown alga)^[1]
• Plebejus argyrognomon (a butterfly; acts as a pheromone)^[8]

See also

• α-Cadinol
• τ-Cadinol

Notes and References

1. 10.3891/acta.chem.scand.20-2893 . (---)-Torreyol ("delta-Cadinol") . 1966 . Westfelt . Lars . Tränkner . Hans . Brandänge . Svante . Walle . Thomas . Sjöberg . Berndt . Bunnenberg . E. . Djerassi . Carl . Records . Ruth . Acta Chemica Scandinavica . 20 . 2893–2894. free .
2. Lars Westfelt (1970), "(−)-Torryeol ('δ-Cadinol')". Acta Chemica Scandinavica volume 24 issue 5 16181622
3. 10.1016/S0040-4020(01)92031-9 . Configurations and conformations of torreyol (δ-cadinol), α-cadinol, T-muurolol and T-cadinol . 1981 . Borg-Karlson . A . Tetrahedron . 37 . 22 . 425. Norin . Torbjörn . Talvitie . Antti .
4. Smolders . R.R. . Structure et configuration absolue du cédrélanol ((−)-δ-cadinol), alcool sesquiterpénique C₁₅H₂₆O l'huile essentielle Cedrela odorata brasiliensis . Canadian Journal of Chemistry . 1967 . 45 . 9 . 889-896. 10.1139/v67-152 .
5. 10.1016/0147-5975(84)90012-4 . Isolation and identification of the sesquiterpenoid (+)-torreyol fromXylobolus frustulatus . 1984 . Vaneijk . G . Roeijmans . H . Verwiel . P . Experimental Mycology . 8 . 3 . 273.
6. 20355025 . 10.1002/jsfa.3799 . Antibacterial activities of essential oils and extracts of TurkishAchillea, SaturejaandThymusspecies against plant pathogenic bacteria . 2010 . Kotan . Recep . Cakir . Ahmet . Dadasoglu . Fatih . Aydin . Tuba . Cakmakci . Ramazan . Ozer . Hakan . Kordali . Saban . Mete . Ebru . Dikbas . Neslihan . Journal of the Science of Food and Agriculture . 90 . 145–60 . 1 .
7. 10.1590/S0103-50532007000500016 . Characterization of woody odorant contributors in copaiba oil (Copaifera multijuga Hayne) . 2007 . Sant'Anna . Beatriz M. P. . Fontes . Silvia Paredes . Pinto . Angelo C. . Rezende . Claudia M. . Journal of the Brazilian Chemical Society . 18 . 5 . 984. free .
8. 10.1007/BF00988581 . Wing scents and scent-released phases in the courtship behavior of Lycaeides argyrognomon (Lepidoptera: Lycaenidae) . 1976 . Lundgren . Lennart . Bergström . Gunnar . Journal of Chemical Ecology . 1 . 4 . 399. 37093578 .