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Terpineol is any of four
MSDS for alpha-terpineol
* {{Authority control Flavors Monoterpenes Alkenols Cyclohexenes
isomer
In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers.
Iso ...
ic monoterpenoids. Terpenoids are terpene that are modified by the addition of a functional group, in this case, an alcohol
Alcohol most commonly refers to:
* Alcohol (chemistry), an organic compound in which a hydroxyl group is bound to a carbon atom
* Alcohol (drug), an intoxicant found in alcoholic drinks
Alcohol may also refer to:
Chemicals
* Ethanol, one of sev ...
. Terpineols have been isolated from a variety of sources such as cardamom, cajuput oil
Cajuput oil is a volatile oil obtained by distillation from the leaves of the myrtaceous trees ''Melaleuca leucadendra'', ''Melaleuca cajuputi'', and probably other ''Melaleuca'' species. The trees yielding the oil are found throughout Maritime ...
, pine oil, and petitgrain
Petitgrain () is an essential oil that is extracted from the leaves and green twigs of the bitter orange tree (''Citrus aurantium'' ssp. ''amara'') via steam distillation. It is also known as petitgrain bigarade.
Etymology
Petitgrain (Fr.: “ ...
oil. Four isomer
In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers.
Iso ...
s exist: α-, β-, γ-terpineol, and terpinen-4-ol. β- and γ-terpineol differ only by the location of the double bond. Terpineol is usually a mixture of these isomers with α-terpineol as the major constituent.
:
Terpineol has a pleasant odor similar to lilac and is a common ingredient in perfumes, cosmetics, and flavors. α-Terpineol is one of the two most abundant aroma constituents of lapsang souchong tea; the α-terpineol originates in the pine smoke used to dry the tea. (+)-α-terpineol is a chemical constituent of skullcap.
Synthesis and biosynthesis
Although it is naturally occurring, terpineol is commonly manufactured from alpha-pinene, which is hydrated in the presence of sulfuric acid. An alternative route starts from limonene: : Limonene reacts with trifluoroacetic acid in aMarkovnikov addition
In organic chemistry, Markovnikov's rule or Markownikoff's rule describes the outcome of some addition reactions. The rule was formulated by Russian chemist Vladimir Markovnikov in 1870.
Explanation
The rule states that with the addition of a p ...
to a trifluoroacetate intermediate, which is easily hydrolyzed with sodium hydroxide
Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula NaOH. It is a white solid ionic compound consisting of sodium cations and hydroxide anions .
Sodium hydroxide is a highly caustic base and alkali ...
to α-terpineol with 7% selectivity. Side-products are β-terpineol in a mixture of the ''cis'' isomer, the ''trans'' isomer, and 4-terpineol.
The biosynthesis of α-terpineol proceeds from geranyl pyrophosphate, which releases pyrophosphate to give the terpinyl cation. This carbocation is the precursor to many terpenes and terpenoids. Its hydrolysis gives terpineol.
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References
External links
MSDS for alpha-terpineol
* {{Authority control Flavors Monoterpenes Alkenols Cyclohexenes