Terpineol
From Wikipedia, the free encyclopedia
| alpha-Terpineol | |
|---|---|
 |
|
| IUPAC 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 |
| Identifiers | |
| CAS number | [98-55-5] |
| SMILES | CC1=CCC(C(C)(O)C)CC1 |
| Properties | |
| Molecular formula | C10H18O |
| Molar mass | 154.25 g/mol |
| Density | 0.9338 g/cm3 |
| Melting point |
39 °C |
| Boiling point |
219 °C |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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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.
[edit] 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
