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δ-Cadinol

1-epi-α-Cadinol 1β-Cadin-4-en-10-ol"},"Section1":{"wt":"{{Chembox Identifiers\n| CASNo = 19435-97-3\n| CASNo_Ref = {{cascite|correct|CAS}}\n| SMILES = CC1=C[C@]2([H])[C@@](CC1)(...

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δ-Cadinol is an organic compound, a sesquiterpenoidalcohol 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 maltagar medium.[5] It also occurs in many conifers,[1] and in many other organisms including

See also

References

  1. ^ Westfelt , Lars ;​ ​Trankner, Hans; Brandänge, Svante; Walle, Thomas; Sjoberg, Berndt; Bunnenberg, E.; Djerassi, Carl; Registros, Ruth (1966). «(---)-Torreyol ("delta-Cadinol")» . Acta Chemica Scandinavica . 20 : 2893–2894 . doi : 10.3891/acta.chem.scand.20-2893 .
  2. ^ Lars Westfelt ( 1970 ), "( - ) -Torryeol ('δ-Cadinol')" . Acta Chemica Scandinavica volumen 24 número 5 16181622 doi : 10.3891/acta.chem.scand.24-1618
  3. ^ Borg -Karlson, A; Norin, Torbjörn; Talvitie, Antti (1981). "Configuraciones y conformaciones de torreyol (δ-cadinol), α-cadinol, T-muurolol y T-cadinol". Tetraedro . 37 (22): 425. doi : 10.1016/S0040-4020(01)92031-9 .
  4. ^ Arde, RR (1967). "Estructura y configuración absoluta del cédrélanol ((-) -δ-cadinol), alcohol sesquiterpénique C 15 H 26 O l'huile essentielle Cedrela odorata brasiliensis ". Revista Canadiense de Química . 45 (9): 889-896. doi : 10.1139/v67-152 .
  5. ↑ Vaneijk, G; Roeijmans, H; Verwiel, P (1984). "Aislamiento e identificación del sesquiterpenoide (+)-torreyol de Xylobolus frustulatus". Micología experimental . 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). "Actividades antibacterianas de aceites esenciales y extractos de especies turcas de Achillea, Satureja y Thymus contra bacterias fitopatógenas". Journal of the Science of Food and Agriculture . 90 (1): 145– 60. doi : 10.1002/jsfa.3799 . PMID 20355025 . 
  7. ↑ Sant'Anna, Beatriz MP; Fontes, Silvia Paredes; Pinto, Angelo C.; Rezende, Claudia M. (2007). "Caracterización de los contribuyentes odoríferos amaderados en el aceite de copaiba (Copaifera multijuga Hayne)" . Journal of the Brazilian Chemical Society . 18 (5): 984. doi : 10.1590/S0103-50532007000500016 .
  8. ↑ Lundgren, Lennart; Bergström, Gunnar (1976). "Aromas de las alas y fases de liberación de aromas en el comportamiento de cortejo de Lycaeides argyrognomon (Lepidoptera: Lycaenidae)". Journal of Chemical Ecology . 1 (4): 399. doi : 10.1007/BF00988581 . S2CID 37093578 .