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Cadinenes

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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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
InChI
  • α: InChI=1S/C15H24/c1-10(2)13-8-6-12(4)14-7-5-11(3)9-15(13)14/h6,9-10,13-15H,5,7-8H2,1-4H3/t13-,14-,15-/m0/s1Key: QMAYBMKBYCGXDH-KKUMJFAQSA-N
  • β: InChI=1S/C15H24/c1-10(2)13-8-6-12(4)14-7-5-11(3)9-15(13)14/h5-6,10,13-15H,7-9H2,1-4H3/t13-,14-,15-/m0/s1Key: USDOQCCMRDNVAH-KKUMJFAQSA-N
  • γ: InChI=1S/C15H24/c1-10(2)13-8-6-12(4)14-7-5-11(3)9-15(13)14/h9-10,13-15H,4-8H2,1-3H3/t13-,14-,15-/m1/s1Key: WRHGORWNJGOVQY-RBSFLKMASA-N
  • δ: InChI=1S/C15H24/c1-10(2)13-8-6-12(4)14-7-5-11(3)9-15(13)14/h9-10,13,15H,5-8H2,1-4H3/t13-,15-/m0/s1Key: FUCYIEXQVQJBKY-ZFWWWQNUSA-N
SMILES
  • α: CC1=C2(CC1)C(=CC2C(C)C)C
  • β: CC1=CC2(C1)(CC=C2C)C(C)C
  • γ: CC1=C2(CC1)C(=C)CC2C(C)C
  • δ: CC1=C2(CCC(=C2CC1)C)C(C)C
Properties
Chemical formula C15H24
Molar mass 204.357 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) 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. 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.
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