|Molar mass||154.25 g·mol−1|
|Melting point||18 °C (64 °F; 291 K)|
|Boiling point||219 °C (426 °F; 492 K) (81 to 82 °C at 4.5 mmHg)|
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
|what is: / ?)(|
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. 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 scullcap.
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 76% selectivity. Side-products are the β-terpineol in a mixture of the cis-isomer, the trans-isomer, and 4-terpineol.
- 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.