Δ-Cadinol

δ-Cadinol
Names
IUPAC name
(1S,4S)-1,6-Dimethyl-4-propan-2-yl-3,4,4a,7,8,8a-hexahydro-2H-naphthalen-1-ol
Other names
Torreyol
1-epi-α-Cadinol
1β-Cadin-4-en-10-ol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
  • InChI=1S/C15H26O/c1-10(2)12-7-8-15(4,16)14-6-5-11(3)9-13(12)14/h9-10,12-14,16H,5-8H2,1-4H3/t12-,13-,14-,15+/m0/s1
    Key: LHYHMMRYTDARSZ-ZQDZILKHSA-N
  • InChI=1/C15H26O/c1-10(2)12-7-8-15(4,16)14-6-5-11(3)9-13(12)14/h9-10,12-14,16H,5-8H2,1-4H3/t12-,13-,14-,15+/m0/s1
    Key: LHYHMMRYTDARSZ-ZQDZILKHBP
  • CC1=C[C@]2([H])[C@@](CC1)([H])[C@](C)(O)CC[C@H]2C(C)C
Properties
C
15H
26O
Molar mass 222.37 g/mol
Appearance White crystalline needles
Melting point 138 to 139 °C (280 to 282 °F; 411 to 412 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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. The (−)-isomer was isolated in 1951 by Haagen-Smit and others from Pinus albicaulus and first called albicaulol. Its structure was determined in 1970 by Lars Westfelt. 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. Lambertol is thought to be either (+)-δ-cadinol or (−)-δ-cadinol. Cedrelanol was originally thought to be identical to (−)-δ-cadinol but was later confirmed to have the structure of τ-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

See also

References

  1. 1 2 3 4 5 6 Westfelt, Lars; Tränkner, Hans; Brandänge, Svante; Walle, Thomas; Sjöberg, Berndt; Bunnenberg, E.; Djerassi, Carl; Records, Ruth (1966). "(---)-Torreyol ("delta-Cadinol")". Acta Chemica Scandinavica. 20: 2893–2894. doi:10.3891/acta.chem.scand.20-2893.
  2. 1 2 3 4 Lars Westfelt (1970), "(−)-Torryeol ('δ-Cadinol')". Acta Chemica Scandinavica volume 24 issue 5 16181622 doi:10.3891/acta.chem.scand.24-1618
  3. 1 2 Borg-Karlson, A; Norin, Torbjörn; Talvitie, Antti (1981). "Configurations and conformations of torreyol (δ-cadinol), α-cadinol, T-muurolol and T-cadinol". Tetrahedron. 37 (22): 425. doi:10.1016/S0040-4020(01)92031-9.
  4. ↑ Smolders, R.R. (1967). "Structure et configuration absolue du cédrélanol ((−)-δ-cadinol), alcool sesquiterpénique C15H26O l'huile essentielle Cedrela odorata brasiliensis". Canadian Journal of Chemistry. 45 (9): 889-896. doi:10.1139/v67-152.
  5. ↑ Vaneijk, G; Roeijmans, H; Verwiel, P (1984). "Isolation and identification of the sesquiterpenoid (+)-torreyol fromXylobolus frustulatus". Experimental Mycology. 8 (3): 273. doi:10.1016/0147-5975(84)90012-4.
  6. ↑ Kotan, Recep; Cakir, Ahmet; Dadasoglu, Fatih; Aydin, Tuba; Cakmakci, Ramazan; Ozer, Hakan; Kordali, Saban; Mete, Ebru; Dikbas, Neslihan (2010). "Antibacterial activities of essential oils and extracts of TurkishAchillea, SaturejaandThymusspecies against plant pathogenic bacteria". Journal of the Science of Food and Agriculture. 90 (1): 145–60. doi:10.1002/jsfa.3799. PMID 20355025.
  7. ↑ Sant'Anna, Beatriz M. P.; Fontes, Silvia Paredes; Pinto, Angelo C.; Rezende, Claudia M. (2007). "Characterization of woody odorant contributors in copaiba oil (Copaifera multijuga Hayne)". Journal of the Brazilian Chemical Society. 18 (5): 984. doi:10.1590/S0103-50532007000500016.
  8. ↑ Lundgren, Lennart; Bergström, Gunnar (1976). "Wing scents and scent-released phases in the courtship behavior of Lycaeides argyrognomon (Lepidoptera: Lycaenidae)". Journal of Chemical Ecology. 1 (4): 399. doi:10.1007/BF00988581. S2CID 37093578.