alpha-Pinene

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α-Pinene
Alpha-Pinene Isomers.svg
(+)-alpha-pinene-3D-balls.png
(+)-α-pinene
(−)-alpha-pinene-3D-balls.png
(−)-α-pinene
Names
IUPAC name
(1S,5S)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene ((−)-α-Pinene)
Identifiers
80-56-8 unspecified YesY
7785-70-8 (+)-α-Pinene
7785-26-4 (−)-α-Pinene
ChEBI CHEBI:28660 YesY
ChemSpider 389795 YesY
Jmol 3D model Interactive image
KEGG C06308 YesY
PubChem 440968
RTECS number DT7000000 (unspec. isomer)
UNII JPF3YI7O34 YesY
  • InChI=1S/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h4,8-9H,5-6H2,1-3H3/t8-,9-/m0/s1 YesY
    Key: GRWFGVWFFZKLTI-IUCAKERBSA-N YesY
  • InChI=1/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h4,8-9H,5-6H2,1-3H3/t8-,9-/m0/s1
    Key: GRWFGVWFFZKLTI-IUCAKERBBG
  • C\1=C(\[C@@H]2C[C@H](C/1)C2(C)C)C
Properties
C10H16
Molar mass 136.24 g·mol−1
Appearance Clear colorless liquid
Density 0.858 g/mL (liquid at 20 °C)
Melting point −64 °C (−83 °F; 209 K)
Boiling point 155 °C (311 °F; 428 K)
Very low
Solubility in acetic acid miscible
Solubility in ethanol miscible
Solubility in acetone miscible
−50.7° (1S,5S-Pinene)
Vapor pressure {{{value}}}
Related compounds
Related alkene
β-Pinene, Camphene, 3-Carene, Limonene
Related compounds
Borneol, Camphor, Terpineol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
Infobox references

α-Pinene is an organic compound of the terpene class, one of two isomers of pinene.[1] 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).[2] Both enantiomers are known in nature; (1S,5S)- or (−)-α-pinene is more common in European pines, whereas the (1R,5R)- or (+)-α-isomer is more common in North America. The racemic mixture is present in some oils such as eucalyptus oil and orange peel oil.

Reactivity

Some general reactions of alpha-pinene

The four-membered ring in α-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 PCl3 cause aromatisation, leading to p-cymene 10.

Under aerobic oxidation conditions, the main oxidation products are pinene oxide, verbenyl hydroperoxide, verbenol and verbenone.[5]

Atmospheric role

Monoterpenes, of which α-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 α-pinene undergoes reactions with ozone, the OH radical or the NO3 radical,[6] 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.[7][8] Products of α-pinene which have been identified explicitly are pinonaldehyde, norpinonaldehyde, pinic acid, pinonic acid and pinalic acid.

Usage

At low exposure levels, α-Pinene is a bronchodilator in humans, and is highly bioavailable with 60% human pulmonary uptake with rapid metabolism or redistribution.[9] α-Pinene is an anti-inflammatory via PGE1,[9] and seems to be a broad-spectrum antibiotic.[10] It exhibits activity as an acetylcholinesterase inhibitor, aiding memory.[9] α-Pinene forms the biosynthetic base for CB2 ligands, such as HU-308.[9]

References

  1. Simonsen, J. L. (1957) The Terpenes (2nd edition) Vol. 2 Cambridge:Cambridge University Press, pp 105-191.
  2. PDR for Herbal Medicine. Montvale, NJ: Medical Economics Company. p. 1100
  3. Richter, G. H. (1945) Textbook of Organic Chemistry, 2nd ed., John Wiley & Sons., New York, PP 663-666.
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  5. U. Neuenschwander (2010), "Mechanism of the Aerobic Oxidation of α-Pinene" (in German), ChemSusChem 3 (1): pp. 75–84, doi:10.1002/cssc.200900228 
  6. IUPAC Subcommittee on Gas Kinetic Data Evaluation
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