Pinene (C

10
H
16
) is a bicyclic monoterpene chemical compound.
There are two structural isomers of pinene found in nature: -pinene and -
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 big sagebrush (Artemisia tridentata). Both isomers are
used by many insects in their chemical



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





-Pinene is an organic compound of the terpene class, one of two isomers of
pinene
.
It is an alkene and it contains a reactive four-membered ring. It is found in
the oils of many species of many coniferous trees, notably the pine. It is also
found in the essential oil of rosemary (Rosmarinus officinalis). Both enantiomers
are known in nature; (1S,5S)- or ()--pinene is more common in European pines,
whereas the (1R,5R)- or (+)--isomer is more common in North America. The
racemic mixture is present in some oils such as eucalyptus oil and orange peel oil.





Chemical Formula: C
10
H
16


Apearance: liquid with a turpentine odour

Melting Point: -55 C

Boiling Point: 156 C

Flash Point: 33 C

Water Solubility: insoluble

Stability: Stable. Flammable. Incompatible with strong oxidizing agents.


The four-membered ring in -pinene 1 makes it a reactive
hydrocarbon, prone to skeletal rearrangements such as the Wagner-
Meerwein rearrangement. For example, attempts to perform hydration
or hydrogen halide addition with the alkene functionality typically lead
to rearranged products. With concentrated sulfuric acid and ethanol
the major products are terpineol 2 and its ethyl ether 3, while glacial
acetic acid gives the corresponding acetate ester 4. With dilute acids,
terpin hydrate 5 becomes the major product.
With one molar equivalent of anhydrous HCl, the simple addition
product 6a can be formed at low temperature in the presence of ether,
but it is very unstable. At normal temperatures, or if no ether is
present, the major product is bornyl chloride 6b, along with a small
amount of fenchyl chloride 6c.
[3]
For many years 6b (also called
"artificial camphor") was referred to as "pinene hydrochloride", until it
was confirmed as identical with bornyl chloride made from camphene.
If more HCl is used, achiral 7 (dipentene hydrochloride) is the major
product along with some 6b. Nitrosyl chloride followed by base leads to
the oxime 8 which can be reduced to "pinylamine" 9. Both 8 and 9 are
stable compounds containing an intact four-membered ring, and these
compounds helped greatly in identifying this important component of
the pinene skeleton.
[4]

A variety of reagents such as iodine or PCl
3
cause aromatisation, leading
to p-cymene 10.
Under aerobic oxidation conditions, the main oxidation products are
pinene oxide, verbenyl hydroperoxide, verbenol and verbenone.





Bicyclo[3.1.1]hept-2-ene, 2,6,6-trimethyl-;2-
Pinene;Pinene;2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene;PINENE,
alpha;2,6,6-Trimethylbicyclo(3.1.1)-2-hept-2-ene;2,6,6-
Trimethylbicyclo(3.1.1)-2-heptene;Acintene A;4,6,6-
Trimethylbicyklo(3,1,1)hept-3-en;UN 2368;alpha-(+)-Pinene;a-
Pinene;Pc 500;Terpene hydrocarbon;c 500;,6,6-Trimethyl-
bicyclo[3.1.1]hept-2-ene;Alpha pinene;2,6,6-trimethylbicyclo[3,1,1]-2-
heptene (alpha&ra


Monoterpenes, of which -pinene is one of the
principal species, are emitted in substantial amounts by vegetation, and
these emissions are affected by temperature and light intensity. In the
atmosphere alpha-pinene undergoes reactions with ozone, the OH
radical or the NO
3
radical, leading to low-volatility species which partly
condense on existing aerosols, thereby generating secondary organic
aerosols. This has been shown in numerous laboratory experiments for
the mono- and sesquiterpenes. Products of -pinene which have been
identified explicitly are pinonaldehyde, norpinonaldehyde, pinic acid,
pinonic acid and pinalic acid.


At low exposure levels, -Pinene is a bronchodilator in
humans, and is highly bioavailable with 60% human pulmonary uptake
with rapid metabolism or redistribution. Alpha-Pinene is an anti-
inflammatory via PGE1, and seems to be a broad-spectrum antibiotic. It
exhibits activity as an acetylcholinesterase inhibitor, aiding memory.
Alpha-Pinene forms the biosynthetic base for CB2 ligands, such as HU-
308.