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Terpineol
 
 
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Terpineol is a naturally occurring monoterpene
Monoterpene

Monoterpenes are a class of terpenes that consist of two isoprene units and have the molecular formula C10H16. Monoterpenes may be linear or contain rings....
 alcohol
Alcohol

In chemistry, an alcohol is any organic compound in which a hydroxyl Functional group is bound to a carbon atom of an alkyl or substituted alkyl group....
 that has been isolated from a variety of sources such as cajuput oil
Cajuput oil

Cajuput oil is a volatile obtained by distillation from the leaves of the Myrtaceae tree Melaleuca leucadendra, and probably other Melaleuca species....
, pine oil
Pine oil

Pine oil is an essential oil obtained by the steam distillation of needles, twigs and cones from a variety of species of pine, particularly Pinus sylvestris....
, and petitgrain
Petitgrain

Petitgrain is an essential oil that is extracted from the leaves and twigs of the bitter orange plant via steam distillation. Its main regions of production are Paraguay and France, with the former's product being of higher odour tenacity....
 oil. There are three isomer
Isomer

In chemistry, isomers are compounds with the same molecular formula but different structural formulae. Isomers do not necessarily share similar properties unless they also have the same functional groups....
s, 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
Alpha-Pinene

a-Pinene is an organic compound of the terpene class, one of two isomers of pinene. It is an alkene and it contains a reactive Cyclobutane. It is found in the oils of many species of many Pinophyta trees, notably the pine....
.

In one study an alternative route was demonstrated starting from d-limonene
Limonene

Limonene is a hydrocarbon, classified as a cyclic terpene. It is a colourless liquid at room temperatures with an extremely strong smell of Orange ....
:

Limonene is reacted with trifluoroacetic acid
Trifluoroacetic acid

Trifluoroacetic acid is the most simple perfluorinated carboxylic acid chemical compound with the formula CF3CO2H. It is a strong carboxylic acid due to the influence of the three very electronegativity fluorine atoms....
 in a Markovnikov addition
Markovnikov's rule

In organic chemistry, Markovnikov's rule or Markownikoff's rule is an observation based on Zaitsev's rule. It was formulated by the Russian chemist Vladimir Vasilevich Markovnikov in 1870 ....
 to a trifluoro acetate intermediate which is easily hydrolyzed with sodium hydroxide
Sodium hydroxide

Sodium hydroxide , also known as lye, caustic soda and sodium hydrate, is a caustic metallic Base . Sodium hydroxide forms a strong alkaline solution when dissolved in a solvent such as water, however, only the hydroxide ion is basic....
 to a-terpineol with 76% selectivity.






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Terpineol is a naturally occurring monoterpene
Monoterpene

Monoterpenes are a class of terpenes that consist of two isoprene units and have the molecular formula C10H16. Monoterpenes may be linear or contain rings....
 alcohol
Alcohol

In chemistry, an alcohol is any organic compound in which a hydroxyl Functional group is bound to a carbon atom of an alkyl or substituted alkyl group....
 that has been isolated from a variety of sources such as cajuput oil
Cajuput oil

Cajuput oil is a volatile obtained by distillation from the leaves of the Myrtaceae tree Melaleuca leucadendra, and probably other Melaleuca species....
, pine oil
Pine oil

Pine oil is an essential oil obtained by the steam distillation of needles, twigs and cones from a variety of species of pine, particularly Pinus sylvestris....
, and petitgrain
Petitgrain

Petitgrain is an essential oil that is extracted from the leaves and twigs of the bitter orange plant via steam distillation. Its main regions of production are Paraguay and France, with the former's product being of higher odour tenacity....
 oil. There are three isomer
Isomer

In chemistry, isomers are compounds with the same molecular formula but different structural formulae. Isomers do not necessarily share similar properties unless they also have the same functional groups....
s, 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
Alpha-Pinene

a-Pinene is an organic compound of the terpene class, one of two isomers of pinene. It is an alkene and it contains a reactive Cyclobutane. It is found in the oils of many species of many Pinophyta trees, notably the pine....
.

In one study an alternative route was demonstrated starting from d-limonene
Limonene

Limonene is a hydrocarbon, classified as a cyclic terpene. It is a colourless liquid at room temperatures with an extremely strong smell of Orange ....
:

Limonene is reacted with trifluoroacetic acid
Trifluoroacetic acid

Trifluoroacetic acid is the most simple perfluorinated carboxylic acid chemical compound with the formula CF3CO2H. It is a strong carboxylic acid due to the influence of the three very electronegativity fluorine atoms....
 in a Markovnikov addition
Markovnikov's rule

In organic chemistry, Markovnikov's rule or Markownikoff's rule is an observation based on Zaitsev's rule. It was formulated by the Russian chemist Vladimir Vasilevich Markovnikov in 1870 ....
 to a trifluoro acetate intermediate which is easily hydrolyzed with sodium hydroxide
Sodium hydroxide

Sodium hydroxide , also known as lye, caustic soda and sodium hydrate, is a caustic metallic Base . Sodium hydroxide forms a strong alkaline solution when dissolved in a solvent such as water, however, only the hydroxide ion is basic....
 to a-terpineol with 76% selectivity. Side products are the ß-terpineol in a mixture of cis-isomer and trans isomer and 4-terpineol.

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