Pinene

The chemical compound pinene is a bicyclic terpene (C₁₀H₁₆, 136.24 g/mol ) known as a monoterpene ^[1]. There are two structural isomers found in nature: α-pinene and β-pinene. As the name suggests, both forms are important constituents of pine resin; they are also found in the resins of many other conifers, and more widely in other plants. Both are also used by many insects in their chemical communication system.

Systematic names are (1S,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-2-ene and (1S,5S)-6,6-dimethyl-2-methylenebicyclo[3.1.1]heptane.

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Isomers

Biosynthesis

α-Pinene and β-pinene are both produced from geranyl pyrophosphate, via cyclisation of linaloyl pyrophosphate followed by loss of a proton from the carbocation equivalent.

Usage

Selective oxidation of pinene with some catalysts in chemical industry give many components for pharmacy, artificial odorants and so on. The primary oxidation product is verbenone.

It can form by simple air oxidation but a synthetic method employs lead tetraacetate ^[2].

Pinenes form the primary constituents of turpentine.

References

1. ^  J. Mann, R. S. Davidson, J. B. Hobbs, D. V. Banthorpe, J. B. Harborne, Natural Products, pp309-311, Addison Wesley Longman Ltd., Harlow, UK, 1994. ISBN 0-582-06009-5.
2. ^  Organic Syntheses, Coll. Vol. 9, p.745 (1998); Vol. 72, p.57 (1995). Article