ALPHA-PINENE

Description

The pinene family of terpenes consists of two structural isomers, α- and β-pinene. Both exist as (+)- and (–)- enantiomers. Turpentine, obtained from pine trees, contains ≈60% α-pinene and ≈30% β-pinene. α-Pinene from North American trees is predominantly the (1R,5R)-(+)-enantiomer (shown), but most European α-pinene is (1S,5S)-(–). Recently, G. Bokinsky and J. D. Keasling?genetically engineered?Escherichia coli?enzymes?to convert switchgrass to sugars and then to pinene for jet fuel.

The Uses of ALPHA-PINENE

β-Pinene is also used in flavor compositions, partly as ingredient in artificial Lemon and Nutmeg oils, partly as component of such type flavors. The concentration in the finished product will be about 15 to 150 ppm. alpha-Pinene has a more balsamic taste, while be~a-Pinene, less suitable for flavors, has a dry-woody character.

Definition

ChEBI: (-)-alpha-pinene is an alpha-pinene. It is an enantiomer of a (+)-alpha-pinene.

Production Methods

beta-pinene can be produced 1) by isolation from American Turpentine (minor component). 2) it is also possible to convert alpha-Pinene into bera-isomer.

Contact allergens

Alpha-pinene is the major constituent of turpentine (about 80%). It exists in levogyre form in European turpentine and in dextrogyre form in turpentine found in North-Americans. Sensitization occurs mainly in painters, polishers, and varnishers, and in those in the perfume and in the ceramics industry.