Alpha-Pinene



Template:DISPLAYTITLE:alpha-Pinene

alpha-Pinene
IUPAC name (1S,5S-2,6,6-trimethyl
bicyclo[3.1.1]hept-2-ene
((−)-Pinene)
Identifiers
CAS number [80-56-8] (unspecified)
[7785-70-8] (+)-α-Pinene
[7785-26-4] (−)-α-Pinene)
RTECS number DT7000000 (unspec. isomer)
SMILES CC1(C)[C@H]2C(C)
=CC[C@@H]1[C@]2(C)C
Properties
Molecular formula C10H16
Molar mass 136.23 g/mol
Appearance Clear, colourless liquid
Density 0.858 g/mL (liquid at 20°C)
Melting point

−64 °C (209 K)

Boiling point

155 °C (428 K)

Solubility in water Very low
Chiral rotation [α]D −50.7°
Hazards
Main hazards flammable
NFPA 704
2
1
0
 
R-phrases 10-20/21/22-36/37/38-43-51
S-phrases 16-26-36-37-60-61
Related Compounds
Related alkene Beta-Pinene, Limonene
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

α-Pinene is an eucalyptus oil.

Reactivity

The four-membered ring in α-pinene 1 makes it a reactive ester 4. With dilute acids, terpin hydrate 5 becomes the major product.

With one molar equivalent of 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 p-cymene 10.


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.
  4. ^ Ruzicka & Trebler, Helv. Chim. Acta. 1921, 4, 566.
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Alpha-Pinene". A list of authors is available in Wikipedia.