Pinocarveol is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon- hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. Th ...

with the formula C₁₀H₁₆O. It is a

bicyclic In chemistry, a bicyclic molecule () is a molecule that features two joined rings. Bicyclic structures occur widely, for example in many biologically important molecules like α-thujene and camphor. A bicyclic compound can be carbocyclic (a ...

monoterpenoid Monoterpenes are a class of terpenes that consist of two isoprene units and have the molecular formula C10H16. Monoterpenes may be linear (acyclic) or contain rings (monocyclic and bicyclic). Modified terpenes, such as those containing oxygen funct ...

, which is a combination of two

isoprene Isoprene, or 2-methyl-1,3-butadiene, is a common volatile organic compound with the formula CH2=C(CH3)−CH=CH2. In its pure form it is a colorless volatile liquid. Isoprene is an unsaturated hydrocarbon. It is produced by many plants and animals ...

units with one

hydroxyl group In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy ...

as a substituent. It exists as either ''trans''- or ''cis''-pinocarveol, referring to

stereochemical Stereochemistry, a subdiscipline of chemistry, involves the study of the relative spatial arrangement of atoms that form the structure of molecules and their manipulation. The study of stereochemistry focuses on the relationships between stereoi ...

orientation of the oxygen as compared to the methylene bridge. It is a naturally occurring molecule in numerous plant species including ''

Eucalyptus globulus ''Eucalyptus globulus'', commonly known as southern blue gum or blue gum, is a species of tall, evergreen tree endemic to southeastern Australia. This ''Eucalyptus'' species has mostly smooth bark, juvenile leaves that are whitish and waxy on ...

'' and ''

Picea abies ''Picea abies'', the Norway spruce or European spruce, is a species of spruce native to Northern, Central and Eastern Europe. It has branchlets that typically hang downwards, and the largest cones of any spruce, 9–17 cm long. It is very clo ...

.'' Pinocarveol is found in a variety of essential oils.

Synthesis

Pinocarveol is formed by heating a mixture of turpentine,

selenium dioxide Selenium dioxide is the chemical compound with the formula SeO2. This colorless solid is one of the most frequently encountered compounds of selenium. Properties Solid SeO2 is a one-dimensional polymer, the chain consisting of alternating seleni ...

, and

hydrogen peroxide Hydrogen peroxide is a chemical compound with the formula . In its pure form, it is a very pale blue liquid that is slightly more viscous than water. It is used as an oxidizer, bleaching agent, and antiseptic, usually as a dilute solution (3% ...

. The selenium dioxide acts as a

catalyst Catalysis () is the process of increasing the rate of a chemical reaction by adding a substance known as a catalyst (). Catalysts are not consumed in the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recyc ...

while the hydrogen peroxide

oxidizes Redox (reduction–oxidation, , ) is a type of chemical reaction in which the oxidation states of substrate change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is the gain of electrons or a de ...

the

pinene Pinene is a collection of unsaturated bicyclic monoterpenes. Two geometric isomers of pinene are found in nature, α-pinene and β-pinene. Both are chiral. As the name suggests, pinenes are found in pines. Specifically, pinene is the major co ...

found in turpentine. The other products in the turpentine are left unreacted.

Use

Pinocarveol is used as a food flavouring. In the European Union it is designated Fl 02.100.

References

Monoterpenes Bicyclic compounds Alcohols {{Chem-stub