Terpineol
| alpha-Terpineol | |
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2-(4-Methyl- 1-cyclohex- 3-enyl) propan- 2-ol |
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Other names
alpha-Terpineol |
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| Identifiers | |
| CAS number | 98-55-5  |
| ChemSpider | 13850142 |
| UNII | 21334LVV8W |
| ChEBI | CHEBI:22469 |
| ChEMBL | CHEMBL507795  |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C10H18O |
| Molar mass | 154.25 g/mol |
| Density | 0.9338 g/cm3 |
| Melting point |
18 °C |
| Boiling point |
219 °C |
| Hazards | |
| MSDS | External MSDS |
| NFPA 704 |
 1
2
0
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 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
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.
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]:
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.
[edit] References
- ^ Merck Index, 11th Edition, 9103.
- ^ Shan-Shan Yao； Wen-Fei Guo； YI Lu； Yuan-Xun Jiang, "Flavor Characteristics of Lapsang Souchong and Smoked Lapsang Souchong,a Special Chinese Black Tea with Pine Smoking Process", Journal of Agricultural and Food Chemistry, Vol. 53, No.22, (2005)
- ^ A Practical Synthesis of d--Terpineol via Markovnikov Addition of d-Limonene Using Trifluoroacetic Acid Yoshifumi Yuasa and Yoko Yuasa Org. Process Res. Dev.; 2006; 10(6) pp 1231 - 1232; (Article) doi:10.1021/op068012d
