nootkatone

Nootkatone is a naturally occurring sesquiterpene ketone found primarily in grapefruit and Alaskan yellow cedar. It is the key aroma compound responsible for the characteristic scent and flavor of grapefruit. Commercially produced from valencene via chemical or biotechnological oxidation processes[3][10], it is used as a flavoring agent in foods and beverages as well as a fragrance ingredient in cosmetics and perfumery[2][8]. Nootkatone has been approved by the US EPA as an active ingredient for use in insecticides and skin-applied repellents due to its effectiveness against ticks (including deer ticks), mosquitoes (including those that transmit Zika virus), bed bugs and other arthropods[1][3][7]. Its mechanism of action involves activation of α‑adrenergic type 1 octopamine receptors in susceptible arthropods leading to fatal spasms[3]. In mammals it shows low toxicity with minimal irritation potential[7], is non-sensitizing to skin or eyes at typical exposure levels[7], and is considered safe for use as a food additive. Preclinical studies suggest additional biological activities including anti-inflammatory effects via AMPK activation in skeletal muscle/liver cells; antiallergic/antiplatelet activity; possible benefits on metabolic-associated fatty liver disease through regulation of glycolipid metabolism by activating AMPK and inhibiting MAPK signaling pathways; anti-obesity effects; improved physical performance; protection against chronic kidney injury; anti-anxiety/antidepressant-like effects—all primarily demonstrated in animal models or cell culture systems rather than clinical trials[5][4].

Other names

(+)-nootkatonenootkartone4.beta.H,5.alpha.-Eremorphila-1(10)11-dien-2-one(4R)-4,4a,5,6,7,8-Hexahydro-4,4aβ-dimethyl-6α-(1-methylethenyl)naphthalen-2(3H)-one(4R,4aS,6R)-4,4a-Dimethyl-6-(prop-1-en-2-yl)-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one2(3H)-Naphthalenone 4 4a 5 6 7 8 hexahydro 44a dimethyl 6 (1 methylethenyl) (FEMA number: FEMA3166)nootkatane