Pinene (C10H16) is a bicyclic monoterpene chemical compound. There are two structural isomers of pinene 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, as well as in non-coniferous plants such as camphorweed (Heterotheca) and big sagebrush (Artemisia tridentata). Both isomers are used by many insects in their chemical communication system. The two isomers of pinene constitute the major component of turpentine.
3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||136.24 g/mol|
|Density||0,86 g·cm−3 (alpha, 15 °C)|
|Melting point||−62 to −55 °C (−80 to −67 °F; 211 to 218 K) (alpha)|
|Boiling point||155 to 156 °C (311 to 313 °F; 428 to 429 K) (alpha)|
|Practically insoluble in water|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
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. Researchers at the Georgia Institute of Technology and the Joint BioEnergy Institute have been able to synthetically produce pinene with a bacterium.
Alpha-pinene appears in conifers and numerous other plants. Pinene is a major component of the essential oils of Sideritis spp. (ironwort) and Salvia spp. (sage). Cannabis also contains alpha-pinene and beta-pinene. Resin from Pistacia terebinthus (commonly known as terebinth or turpentine tree) is rich in pinene. Pine nuts produced by pine trees contain pinene.
The racemic mixture of the two forms of pinene is found in some oils like eucalyptus oil.
In chemical industry, selective oxidation of pinene with some catalysts gives many compounds for perfumery, such as artificial odorants. An important oxidation product is verbenone, along with pinene oxide, verbenol, and verbenyl hydroperoxide.
Pinenes are the primary constituents of turpentine.
- Record of alpha-Pinen in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 07-January-2016.
- Record of beta-Pinen in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 07-January-2016.
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