Δ-Cadinol

{{lowercase title}} {{Chembox | Name = δ-Cadinol | ImageFile = delta-cadinol.svg | ImageAlt = | IUPACName = (1''S'',4''S'')-1,6-Dimethyl-4-propan-2-yl-3,4,4a,7,8,8a-hexahydro-2''H''-naphthalen-1-ol | OtherNames = Torreyol 1-epi-α-Cadinol 1β-Cadin-4-en-10-ol |Section1={{Chembox Identifiers | CASNo = 19435-97-3 | CASNo_Ref = {{cascite|correct|CAS}} | SMILES = CC1=C[C@]2([H])[C@@](CC1)([H])[C@](C)(O)CC[C@H]2C(C)C | PubChem = 3084311 | ChemSpiderID = 2341398 | ChEBI = 156223 | 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 | InChIKey = LHYHMMRYTDARSZ-ZQDZILKHBP | StdInChI = 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 | StdInChIKey = LHYHMMRYTDARSZ-ZQDZILKHSA-N }} |Section2={{Chembox Properties | Formula = {{chem|C|15|H|26|O}} | MolarMass = 222.37 g/mol | Appearance = White crystalline needles | Density = | MeltingPtC = 138 to 139 | BoilingPt = | Solubility = }} }}

'''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 '''(−)-'''.<ref name=westf66>{{cite journal | doi = 10.3891/acta.chem.scand.20-2893 | title = (---)-Torreyol ("delta-Cadinol") | year = 1966 | last1 = Westfelt | first1 = Lars | last2 = Tränkner | first2 = Hans | last3 = Brandänge | first3 = Svante | last4 = Walle | first4 = Thomas | last5 = Sjöberg | first5 = Berndt | last6 = Bunnenberg | first6 = E. | last7 = Djerassi | first7 = Carl | last8 = Records | first8 = Ruth | journal = Acta Chemica Scandinavica | volume = 20 | pages = 2893–2894| doi-access = free }}</ref><ref name=westf70>Lars Westfelt (1970), "(−)-Torryeol ('δ-Cadinol')". ''Acta Chemica Scandinavica'' volume 24 issue 5 16181622 {{doi|10.3891/acta.chem.scand.24-1618}}</ref> The (+)-isomer was identified by E. Shinozaki in 1922 from the leaves of ''Torreya nucifera'' and originally named '''torreyol'''.<ref name=westf66/> The (−)-isomer was isolated in 1951 by Haagen-Smit and others from ''Pinus albicaulus'' and first called '''albicaulol'''.<ref name=westf66/> Its structure was determined in 1970 by Lars Westfelt.<ref name=westf70/> 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.<ref name=westf70/><ref name=borg>{{cite journal | doi = 10.1016/S0040-4020(01)92031-9 | title = Configurations and conformations of torreyol (δ-cadinol), α-cadinol, T-muurolol and T-cadinol | year = 1981 | last1 = Borg-Karlson | first1 = A | journal = Tetrahedron | volume = 37 | issue = 22 | pages = 425| last2 = Norin | first2 = Torbjörn | last3 = Talvitie | first3 = Antti }}</ref> '''Lambertol''' is thought to be either (+)-δ-cadinol or (−)-δ-cadinol.<ref name=westf70/> '''Cedrelanol''' was originally thought to be identical to (−)-δ-cadinol but was later confirmed to have the structure of τ-cadinol.<ref name="Smolders1967">{{cite journal |last1=Smolders |first1=R.R. |title=Structure et configuration absolue du cédrélanol ((−)-δ-cadinol), alcool sesquiterpénique C15H26O l'huile essentielle ''Cedrela odorata brasiliensis'' |journal=Canadian Journal of Chemistry |date=1967 |volume=45 |issue=9 |page=889-896|doi=10.1139/v67-152 }}</ref>

==Occurrence== δ-Cadinol is produced by the fungus ''Xylobolus frustulatus'' as long white needles when grown in malt agar medium.<ref name=eijk>{{cite journal | doi = 10.1016/0147-5975(84)90012-4 | title = Isolation and identification of the sesquiterpenoid (+)-torreyol fromXylobolus frustulatus | year = 1984 | last1 = Vaneijk | first1 = G | last2 = Roeijmans | first2 = H | last3 = Verwiel | first3 = P | journal = Experimental Mycology | volume = 8 | issue = 3 | pages = 273}}</ref> It also occurs in many conifers,<ref name=westf66/> and in many other organisms including * ''Achillea millefolium'' (6%)<ref name=kotan>{{cite journal | pmid = 20355025 | doi = 10.1002/jsfa.3799 | title = Antibacterial activities of essential oils and extracts of TurkishAchillea, SaturejaandThymusspecies against plant pathogenic bacteria | year = 2010 | last1 = Kotan | first1 = Recep | last2 = Cakir | first2 = Ahmet | last3 = Dadasoglu | first3 = Fatih | last4 = Aydin | first4 = Tuba | last5 = Cakmakci | first5 = Ramazan | last6 = Ozer | first6 = Hakan | last7 = Kordali | first7 = Saban | last8 = Mete | first8 = Ebru | last9 = Dikbas | first9 = Neslihan | journal = Journal of the Science of Food and Agriculture | volume = 90 | pages = 145–60 | issue = 1 }}</ref> * ''Cedrela odorata''<ref name=westf66/> * ''Clitocybe illudens'' (a mushroom)<ref name=borg/> * ''Copaifera multijuga'' (1%; a major contributor to the aroma of copaiba oil)<ref name=stanna>{{cite journal | doi = 10.1590/S0103-50532007000500016 | title = Characterization of woody odorant contributors in copaiba oil (Copaifera multijuga Hayne) | year = 2007 | last1 = Sant'Anna | first1 = Beatriz M. P. | last2 = Fontes | first2 = Silvia Paredes | last3 = Pinto | first3 = Angelo C. | last4 = Rezende | first4 = Claudia M. | journal = Journal of the Brazilian Chemical Society | volume = 18 | issue = 5 | pages = 984| doi-access = free }}</ref> * ''Dictyopteris divaricata'' (a brown alga)<ref name=westf66/> * ''Plebejus argyrognomon'' (a butterfly; acts as a pheromone)<ref name=lund>{{cite journal | doi = 10.1007/BF00988581 | title = Wing scents and scent-released phases in the courtship behavior of Lycaeides argyrognomon (Lepidoptera: Lycaenidae) | year = 1976 | last1 = Lundgren | first1 = Lennart | last2 = Bergström | first2 = Gunnar | journal = Journal of Chemical Ecology | volume = 1 | issue = 4 | pages = 399| s2cid = 37093578 }}</ref>

==See also== * α-Cadinol * τ-Cadinol

==References== {{reflist}}

{{DEFAULTSORT:Cadinol, delta-}} Category:Sesquiterpenes