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词条 Delta-Cadinol
释义

  1. Occurrence

  2. See also

  3. References

{{DISPLAYTITLE:delta-Cadinol}}{{Chembox
| Name = δ-Cadinol
| ImageFile = delta-cadinol.svg
| ImageAlt =
| IUPACName = (1S,4S)-1,6-Dimethyl-4-propan-2-yl-3,4,4a,7,8,8a-hexahydro-2H-naphthalen-1-ol
| OtherNames =
|Section1={{Chembox Identifiers
| CASNo = 36564-42-8
| SMILES = CC1=C[C@]2([H])[C@@](CC1)([H])[C@](C)(O)CC[C@H]2C(C)C
| PubChem = 3084311
| ChemSpiderID = 2341398
| 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 also called torreyol, sesquigoyol, pilgerol, cedrelanol, lambertol, and albicaulol.[1][2]

The names may refer to any of two isomers distinguished by the prefixes (+)- and (−)-.[3][4] The (+)-isomer was identified by E. Shinozaki in 1922 from the leaves of Torreya nucifera.[3] The (−)-isomer was isolated in 1951 by Haagen-Smit and others from Pinus albicaulus.[3] Its structure was determined in 1970 by Lars Westfelt.[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,[3] and in many other organisms including

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

See also

  • α-Cadinol
  • τ-Cadinol

References

1. ^{{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 }}
2. ^{{cite journal | author = V. Herout, V. Sýkora | year = 1958 | title = The chemistry of cadinenes and cadinols | journal = Tetrahedron | volume = 4 | pages = 246–255 | doi = 10.1016/0040-4020(58)80046-0 | issue = 3–4}}
3. ^{{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}}
4. ^Lars Westfelt (1970), "(−)-Torryeol ('δ-Cadinol')". Acta Chemica Scandinavica volume 24 issue 5 16181622 {{doi|10.3891/acta.chem.scand.24-1618}}
5. ^{{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}}
6. ^{{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 }}
7. ^{{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}}
8. ^{{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}}
{{DEFAULTSORT:Cadinol, delta-}}

1 : Sesquiterpenes

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