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Terpineol
| alpha-Terpineol |
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| 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 [2]:
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
- ^ Merck Index, 11th Edition, 9103.
- ^ 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
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This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Terpineol". A list of authors is available in Wikipedia.
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