Phellandrene Explained

Phellandrenes are 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 diethyl ether.

α-Phellandrene was named after Eucalyptus phellandra, now called Eucalyptus radiata, from which it can be isolated.[1] It is also a constituent of the essential oil of Eucalyptus dives.[2] 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 α-phellandrene isomer can form hazardous and explosive peroxides on contact with air at elevated temperatures.[3]

Biosynthesis

The biosynthesis of phellandrene begins with dimethylallyl pyrophosphate and isopentenyl pyrophosphate condensing in an SN1 reaction to form geranyl pyrophosphate. The resultant monoterpene undergoes cyclization to form a menthyl cationic species. A hydride shift then forms an allylic carbocation. Finally, an elimination reaction occurs at one of two positions, yielding either α-phellandrene or β-phellandrene.[4]

Notes and References

  1. Jacobs, S.W.L., Pickard, J., Plants of New South Wales, 1981, .
  2. Boland, D. J., Brophy, J. J., and A. P. N. House, Eucalyptus Leaf Oils, 1991, .
  3. Book: Urben, Peter . Bretherick's Handobook of Reactive Chemical Hazards . Butterworth-Heinemann . 2007 . 1 . 7 . 1154.
  4. Book: Medicinal natural products : a biosynthetic approach. Dewick, Paul M. . 9 March 2009 . 9780470741689 . 3rd . Chichester, West Sussex, United Kingdom . 259265604.