Terpinen-4-ol is an isomer of

terpineol Terpineol is any of four isomeric monoterpenoids. Terpenoids are terpene that are modified by the addition of a functional group, in this case, an alcohol. Terpineols have been isolated from a variety of sources such as cardamom, cajuput oil, ...

with the chemical formula C₁₀H₁₈O. A primary constituent of

tea tree oil Tea tree oil, also known as melaleuca oil, is an essential oil with a fresh, camphoraceous odour and a colour that ranges from pale yellow to nearly colourless and clear. It is derived from the leaves of the tea tree, '' Melaleuca alternif ...

, it is obtained as an

extract An extract (essence) is a substance made by extracting a part of a raw material, often by using a solvent such as ethanol, oil or water. Extracts may be sold as tinctures or absolutes or dried and powdered. The aromatic principles of ma ...

from the leaves, branches, and bark of '' Melaleuca alternifolia'' Cheel. Despite considerable

basic Basic or BASIC may refer to: Science and technology * BASIC, a computer programming language * Basic (chemistry), having the properties of a base * Basic access authentication, in HTTP Entertainment * Basic (film), ''Basic'' (film), a 2003 film ...

and preliminary

clinical research Clinical research is a branch of medical research that involves people and aims to determine the effectiveness (efficacy) and safety of medications, devices, diagnostic products, and treatment regimens intended for improving human health. The ...

of terpinen-4-ol and tea tree oil, its biological properties and potential for clinical uses have not been established as of 2019. It may be a factor in the

contact dermatitis Contact dermatitis is a type of acute or chronic inflammation of the skin caused by exposure to chemical or physical agents. Symptoms of contact dermatitis can include itchy or dry skin, a red rash, bumps, blisters, or swelling. These rashes ...

of tea tree oil when used topically. Terpinen-4-ol occurs in ''

Juniperus communis ''Juniperus communis'', the common juniper, is a species of small tree or shrub in the cypress family Cupressaceae. An evergreen conifer, it has the largest geographical range of any woody plant, with a circumpolar distribution throughout the coo ...

'' and is thought to be the reason why this wood is highly resistant to rot.

Synthesis

Terpinen-4-ol can be synthesized from

terpinolene The terpinenes are a group of isomeric hydrocarbons that are classified as monoterpenes. They each have the same molecular formula and carbon framework, but they differ in the position of carbon-carbon double bonds. α-Terpinene has been isolate ...

(1) by photooxidation, reduction of the resulting hydroperoxide (2), and selective

hydrogenation Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to redox, reduce or Saturated ...

of the terminal double bond in 3. :

References

{{reflist Monoterpenes Cyclohexenols