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 (what is this?)  (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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.

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

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. ^ ^{a b c} Record of alpha-Pinen in the GESTIS Substance Database from the BGIA
2. ^ Record of beta-Pinen in the GESTIS Substance Database from the BGIA

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