Terpineol
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| alpha-Terpineol | |
|---|---|
| Image:Alpha-Terpineol.png | |
| Chemical name | 2-(4-Methyl-1-cyclohex-3-enyl)propan-2-ol |
| Other names | alpha-Terpineol α-Terpineol p-Menth-1-en-8-ol α,α,4-Trimethylcyclohex-3-ene-1-methanol Terpene alcohol |
| Chemical formula | C10H18O |
| Molecular mass | 154.25 g/mol |
| CAS number | [98-55-5] |
| Density | 0.9338 g/cm3 |
| Melting point | 39 °C |
| Boiling point | 219 °C 81-82 °C at 4.5 mmHg |
| SMILES | CC1=CCC(C(C)(O)C)CC1 |
| Disclaimer and 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.
Although it is naturally occurring, terpineol is commonly manufactured from the more readily available alpha-pinene.
In one study an alternative route was demonstrated starting from d-limonene [1]:
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.
References
External links
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