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Nootkatone

Chemical compound From Wikipedia, the free encyclopedia

Nootkatone
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Nootkatone is an organic compound, a sesquiterpenoid, which means that it is a C15 derivative that also contains an oxygen-containing functional group (a ketone). It is the most valuable aroma compound of grapefruit.[2] Nootkatone was originally isolated from the wood of the Alaskan yellow cedar, Cupressus nootkatensis. The species name, nootkatensis, is derived from the language of the Nuu-Chah-Nulth people of Canada (formerly referred to as the Nootka people).[3]

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Production

Nootkatone is produced commercially from valencene, another more abundant sesquiterpene.[4]

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The conversion of valencene to nootkatone is an example of allylic oxidation.

Allylix (Now Lallemand of Montreal, PQ), developed a fermentation process to nootkatone.[5][6]

Mechanism of action

As is true of other plant terpenoids, nootkatone activates α-adrenergic type 1 octopamine receptor (PaOA1) in susceptible arthropods, causing fatal spasms.[7]

Uses

Nootkatone in spray form is an effective repellent or insecticide against deer ticks[8][9][10] and lone star ticks.[9][10] It is also an effective repellent or insecticide against mosquitos, and may repel bed bugs, head lice, Formosan termites,[11] and other insects.[12] It is an environmentally friendly insecticide because it is a volatile essential oil that does not persist in the environment.[12] It was approved by the U.S. EPA for this use on August 10, 2020.[13] Its ability to repel ticks, mosquitoes, and other insects may last for hours, in contrast to other plant-based oil repellants like citronella, peppermint oil, and lemongrass oil.[14] It is nontoxic to humans, is an approved food additive,[12] and is commonly used in foods, cosmetics, and pharmaceuticals.[8] The CDC has licensed patents to two companies to produce an insecticide and an insect repellant.[12]

See also

References

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