Nootkatone
Chemical compound
From Wikipedia, the free encyclopedia
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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| Names | |
|---|---|
| IUPAC name
4α,5α-Eremophila-1(10),11-dien-2-one | |
| Systematic IUPAC name
(4R,4aS,6R)-4,4a-Dimethyl-6-(prop-1-en-2-yl)-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one | |
| Other names
(+)-nootkatone | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.022.840 |
| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C15H22O | |
| Molar mass | 218.340 g·mol−1 |
| Appearance | Clear or white crystals, impure samples appear as a viscous yellow liquid |
| Density | 0.968 g/mL |
| Melting point | 36 °C (97 °F; 309 K) |
| Boiling point | 170 °C (338 °F; 443 K) |
| Insoluble in water, very soluble in ethanol, dichloromethane, ethyl acetate, soluble in hexanes | |
| Hazards | |
| GHS labelling:[1] | |
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| Warning | |
| H317 | |
| P280 | |
| Flash point | ~ 100 °C (212 °F; 373 K) |
| Related compounds | |
Related terpenes |
Valencene |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Production
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]