Terpineol is any of four isomericmonoterpenoids. Terpenoids are terpene that are modified by the addition of a functional group, in this case, an alcohol. Terpineols have been isolated from a variety of sources such as cardamom, cajuput oil, pine oil, and petitgrain oil.[1] Four isomers exist: α-terpineol, β-terpineol, γ-terpineol, and terpinen-4-ol. β-Terpineol and γ-terpineol differ only by the location of the double bond. Terpineol is usually a mixture of these isomers with α-terpineol as the major constituent.
File:Terpineols.svgTerpineols: alpha-, beta-, gamma-, and the 4-terpineol isomer
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] (+)-α-Terpineol is a chemical constituent of skullcap.
Synthesis and biosynthesis
Although it is naturally occurring, terpineol is commonly manufactured from alpha-pinene, which is hydrated in the presence of sulfuric acid.[3]
The biosynthesis of α-terpineol proceeds from geranyl pyrophosphate, which releases pyrophosphate to give the terpinyl cation. This carbocation is the precursor to many terpenes and terpenoids. Its hydrolysis gives terpineol.
