Terpineol

Terpineol is a naturally occurring monoterpene alcohol that has been derived from cajuput oil, pine oil, and petitgrain oil. There are three isomers, alpha-, beta-, and gamma-terpineol, where the last two are different by the location of the double bond. Terpineol is usually a mixture of these isomers with alpha-terpineol as the major component. It gives off a pleasant odor similar to a lilac making it a common ingredient in perfumes, cosmetics, and flavors. Terpineol is used in a wide variety of products including solvent for ethylcellulose, plasticizer for epoxy resin, fragrance, electronic cleaner.

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. [|[2]] Although it is naturally occurring, terpineol is commonly manufactured from the more readily available [|alpha-pinene]. In one study, an alternative route starting from [|d-limonene] was demonstrated [|[3]] :
 * Terpineol** is a naturally occurring [|monoterpene] [|alcohol] that has been isolated from a variety of sources such as [|cajuput oil], [|pine oil] , and [|petitgrain] oil [|[1]] . There are three [|isomers] , //alpha//-, //beta//-, and //gamma//-terpineol, the last two differing only by the location of the [|double bond] . Terpineol is usually a mixture of these isomers with //alpha//-terpineol as the major constituent.

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