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.
|Preferred IUPAC name
3D model (JSmol)
|Molar mass||154.253 g·mol−1|
|Melting point||−35.9 to −28.2 °C (−32.6 to −18.8 °F; 237.2 to 245.0 K) (mixture of isomers)|
|Boiling point||214–217 °C (417–423 °F; 487–490 K) (mixture of isomers)|
|Safety data sheet||External MSDS|
|Flash point||88 °C (190 °F; 361 K)|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
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.
Although it is naturally occurring, terpineol is commonly manufactured from the more readily available alpha-pinene.
Limonene is reacted with trifluoroacetic acid in a Markovnikov addition to a trifluoroacetate intermediate, which is easily hydrolyzed with sodium hydroxide to α-terpineol with 7% selectivity. Side-products are the β-terpineol in a mixture of the cis-isomer, the trans-isomer, and 4-terpineol.
- Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
- Merck Index, 11th Edition, 9103
- Shan-Shan Yao; Wen-Fei Guo; Yi Lu; Yuan-Xun Jiang (2005). "Flavor Characteristics of Lapsang Souchong and Smoked Lapsang Souchong, a Special Chinese Black Tea with Pine Smoking Process". Journal of Agricultural and Food Chemistry. 53 (22): 8688–93. doi:10.1021/jf058059i. PMID 16248572.
- Yuasa, Yoshifumi; Yuasa, Yoko (2006). "A Practical Synthesis ofd-α-Terpineol via Markovnikov Addition ofd-Limonene Using Trifluoroacetic Acid". Organic Process Research & Development. 10 (6): 1231–1232. doi:10.1021/op068012d.