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Nootkatone

Nootkatone

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. 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).

Production

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

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

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

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.

Uses

Nootkatone in spray form is an effective repellent or insecticide against deer ticks{{Cite journal

References

References

  1. GHS: [https://www.sigmaaldrich.com/NL/en/product/ALDRICH/74437 Sigma-Aldrich 74437] (SDS)
  2. Furusawa, Mai. (November 2005). "Highly Efficient Production of Nootkatone, the Grapefruit Aroma from Valencene, by Biotransformation". Chem. Pharm. Bull..
  3. "Cupressus nootkatensis / Nootka cypress | Conifer Species".
  4. (2016). "Scalable and sustainable electrochemical allylic C–H oxidation". Nature.
  5. "Cost effective fermentation replaces costly extraction". Allylix.
  6. Bigelow, Bruce. (2011-04-28). "Nootkatone, So A-peeling in Grapefruit, is Repellent to Mosquitoes and Ticks". xconomy.com.
  7. (2018). "Advances in the Biorational Control of Medical and Veterinary Pests".
  8. Jan Suszkiw. (January 2011). "Lignin + Nootkatone = Dead Ticks". USDA.
  9. (Dec 2009). "Ability of two natural products, nootkatone and carvacrol, to suppress ''Ixodes scapularis'' and ''Amblyomma americanum'' (Acari: Ixodidae) in a Lyme disease endemic area of New Jersey". J Econ Entomol.
  10. (March 2001). "Nootkatone is a repellent for Formosan subterranean termite (Coptotermes formosanus)". J Chem Ecol.
  11. Richard Knox. (April 18, 2011). "Repelling Bugs with the Essence of Grapefruit". [[NPR]].
  12. (10 August 2020). "EPA approves nootkatone".
  13. McNeil, Donald G. Jr.. (2020-08-11). "Citrus Flavoring Is Weaponized Against Insect-Borne Diseases". nytimes.com.
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This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

flavors enones sesquiterpenes decalins alkene-derivatives
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