Terpineol

Terpineol is a monoterpene alcohol that has been isolated from a variety of sources such as cajuput oil, pine oil, and petitgrain oil.There are four isomers, alpha-, beta-, gamma-terpineol, and terpinen-4-ol. Beta- and gamma-terpineol differ only by the location of the double bond. Terpineol is usually a mixture of these isomers with alpha-terpineol as the major constituent.

Terpineol has a pleasant odor similar to lilac and is a common ingredient in perfumes, cosmetics, and flavors. α-Terpineol is one of the two most abundant aroma constituents of lapsang souchong tea; the α-terpineol originates in the pine smoke used to dry the tea. (+)-α-Terpineol is a chemical constituent of skullcap.

 

Synthesis

 

Although it is naturally occurring, terpineol is commonly manufactured from the more readily available alpha-pinene.

Terpineol synthesis from limonene

Limonene is reacted with trifluoroacetic acid in a Markovnikov addition to a trifluoroacetate intermediate, which is easily hydrolysed with sodium hydroxide to α-terpineol with 76% selectivity. Side-products are the β-terpineol in a mixture of the cis-isomer, the trans-isomer, and 4-terpineol.