Cadinenes

Cadinenes
α-Cadinene
α-Cadinene
α-Cadinene
β-Cadinene
γ-Cadinene
δ-Cadinene
Names
IUPAC names
  • (1S,4aR,8aR)-4,7-dimethyl-1-(propan-2-yl)- 1,2,4a,5,6,8a-hexahydronaphthalene (α-cadinene)
  • (1S,4aR,8aR)-7-methyl-4-methylidene-1-(propan-2-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalene (γ-cadinene)
  • (1S,8aR)-4,7-dimethyl-1-(propan-2-yl)-1,2,3,5,6,8a-hexahydronaphthalene (δ-cadinene)
Identifiers
CAS Number
  • α: 24406-05-1 checkY
  • β: 11044-40-9 checkY
  • γ: 39029-41-9 checkY
  • δ: 1460-97-5 checkY
ChEBI
  • α: CHEBI:80749
  • β: CHEBI:27723
  • γ: CHEBI:63203
  • δ: CHEBI:15385
ChEMBL
  • β: ChEMBL3120653
  • δ: ChEMBL445759
KEGG
  • α: C16815
  • β: C09625
  • γ: C19738
  • δ: C06394
PubChem CID
  • α: 12306048
  • β: 10657
  • γ: 92313
  • δ: 441005
UNII
  • α: X650G04I0A checkY
  • β: Z07LA0GY4J checkY
  • γ: 2GHT32E0JU checkY
  • δ: 7848KI47OS checkY
Properties
Chemical formula
 C15H24
Molar mass 204.357 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Chemical compound

Cadinenes are a group of isomeric hydrocarbons that occur in a wide variety of essential oil-producing plants. The name is derived from that of the Cade juniper (Juniperus oxycedrus L.), the wood of which yields an oil from which cadinene isomers were first isolated.

Chemically, the cadinenes are bicyclic sesquiterpenes. The term cadinene has sometimes also been used in a broad sense to refer to any sesquiterpene with the so-called cadalane (4-isopropyl-1,6-dimethyldecahydronaphthalene) carbon skeleton. Because of the large number of known double-bond and stereochemical isomers, this class of compounds has been subdivided into four subclasses based on the relative stereochemistry at the isopropyl group and the two bridgehead carbon atoms.[1] The name cadinene is now properly used only for the first subclass below, which includes the compounds originally isolated from cade oil. Only one enantiomer of each subclass is depicted, with the understanding that the other enantiomer bears the same subclass name.

  • Cadalane skeleton
    Cadalane skeleton
  • Cadinane stereochemistry
    Cadinane stereochemistry
  • Muurolane stereochemistry
    Muurolane stereochemistry
  • Amorphane stereochemistry
    Amorphane stereochemistry
  • Bulgarane stereochemistry
    Bulgarane stereochemistry

References

  1. ^ A.-K. Borg-Karlson, T. Norin and A. Talvitie (1981). "Configurations and conformations of torreyol (δ-cadinol), α-cadinol, T-muurolol and T-cadinol". Tetrahedron. 37 (2): 425–430. doi:10.1016/s0040-4020(01)92031-9.