pinene

Pinene
IUPAC name (1S,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-2-ene or (1S,5S)-6,6-dimethyl-2-methylenebicyclo[3.1.1]heptane
Identifiers
CAS number	80-56-8 Y, (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
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Pinene (C₁₀H₁₆) is a bicyclic monoterpene chemical compound.^[1] 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. Both isomers are used by many insects in their chemical communication system.

Isomers

skeletal formula
perspective view	X		X
ball-and-stick model	X		X
name	(1R)-(+)-α-pinene	(1S)-(−)-α-pinene	(1R)-(+)-β-pinene	(1S)-(−)-β-pinene
CAS number	7785-70-8	7785-26-4	19902-08-0	18172-67-3

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

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. ^[3]

Pinenes are the primary constituents of turpentine.

References

1. ^ ^{a b c} Record of alpha-Pinen in the GESTIS Substance Database from the IFA, accessed on 24. January 2008
2. ^ Record of beta-Pinen in the GESTIS Substance Database from the IFA, accessed on 24. January 2008
3. ^ U. Neuenschwander: Mechanism of the Aerobic Oxidation of α-Pinene. In: ChemSusChem. 3, No. 1, 16 November 2011, p. 75–84 (doi:10.1002/cssc.200900228). 

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

External links