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Phellandrene

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α-Phellandrene (left) and β-Phellandrene (right)
α-Phellandrene
α-Phellandrene
β-Phellandrene
β-Phellandrene
Names
IUPAC names α: 2-Methyl-5-(1-methylethyl)-1,3-cyclohexadiene
β: 3-Methylene-6-(1-methylethyl)cyclohexene
Identifiers
CAS Number
3D model (JSmol)
ECHA InfoCard 100.014.121 Edit this at Wikidata
CompTox Dashboard (EPA)
SMILES
  • α: CC(C)C1CC=C(C)C=C1
    β: CC(C)C1CCC(=C)C=C1
Properties
Chemical formula C10H16
Molar mass 136.24 g/mol
Appearance Colorless oil (α and β)
Density α: 0.846 g/cm
β: 0.85 g/cm
Boiling point α: 171-172 °C
β: 171-172 °C
Solubility in water Insoluble (α and β)
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

Phellandrene is the name for a pair of organic compounds that have a similar molecular structure and similar chemical properties. α-Phellandrene and β-phellandrene are cyclic monoterpenes and are double-bond isomers. In α-phellandrene, both double bonds are endocyclic and in β-phellandrene, one of them is exocyclic. Both are insoluble in water, but miscible with ether.

α-Phellandrene was named after Eucalyptus phellandra, now called Eucalyptus radiata, from which it can be isolated. It is also a constituent of the essential oil of Eucalyptus dives. β-Phellandrene has been isolated from the oil of water fennel and Canada balsam oil.

The phellandrenes are used in fragrances because of their pleasing aromas. The odor of β-phellandrene has been described as peppery-minty and slightly citrusy.

The alpha phellandrene isomer can form hazardous and explosive peroxides on contact with air at elevated temperature.

References

  1. The Merck Index, 12th Edition, 7340, 7341
  2. Jacobs, S.W.L., Pickard, J., Plants of New South Wales, 1981, ISBN 0-7240-1978-2.
  3. Boland, D.J., Brophy, J.J., and A.P.N. House, Eucalyptus Leaf Oils, 1991, ISBN 0-909605-69-6.
  4. Urben, Peter (2007). Bretherick's Handobook of Reactive Chemical Hazards. Vol. 1 (7 ed.). Butterworth-Heinemann. p. 1154.
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