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| Pinene | |
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| IUPAC name | Pinene |
| Identifiers | |
| CAS number | [80-56-8] (unspecified) [7785-70-8] (1R-α) [7785-26-4] (1S-α) [2437-95-8] ((±)-α) [18172-67-3] (β) |
| Properties | |
| Molecular formula | C10H16 |
| Molar mass | 136.24 g/mol |
| Appearance | Liquid |
| Density | 0,86 g·cm−3 (alpha, 15 °C)[1][2] |
| Melting point |
−62–−55 °C (alpha)[1] |
| Boiling point |
155–156 °C (alpha)[1] |
| Solubility in water | Practically insoluble in water |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references |
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The chemical compound pinene is a bicyclic terpene (C10H16, 136.24 g/mol ) known as a monoterpene . 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
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-(%2B)-alpha-pinene-2D-skeletal.png) |
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-(-)-alpha-pinene-2D-projected-skeletal.png) |
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-(-)-beta-pinene-2D-projected-skeletal.png) |
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-(%E2%88%92)-alpha-pinene-from-xtal-3D-balls.png) |
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-(%E2%88%92)-beta-pinene-from-xtal-3D-balls.png) |
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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 .
Pinenes form the primary constituents of turpentine.
References
- ^ a b c Record of alpha-Pinen in the GESTIS Substance Database from the BGIA
- ^ Record of beta-Pinen in the GESTIS Substance Database from the BGIA
- ^ 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.
- ^ Organic Syntheses, Coll. Vol. 9, p.745 (1998); Vol. 72, p.57 (1995). Article
External links
Wikipedia content modification information:
- This page was last modified on 26 July 2008, at 16:46.
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