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Terpineol

alpha-Terpineol

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.

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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

Categories: Terpenes and terpenoids | Alcohols