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Nootkatone

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Nootkatone
Nootkatone crystals
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)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.022.840 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C15H22O/c1-10(2)12-5-6-13-8-14(16)7-11(3)15(13,4)9-12/h8,11-12H,1,5-7,9H2,2-4H3/t11-,12-,15+/m1/s1 checkY
    Key: WTOYNNBCKUYIKC-JMSVASOKSA-N checkY
  • InChI=1/C15H22O/c1-10(2)12-5-6-13-8-14(16)7-11(3)15(13,4)9-12/h8,11-12H,1,5-7,9H2,2-4H3/t11-,12-,15+/m1/s1
    Key: WTOYNNBCKUYIKC-JMSVASOKBQ
  • O=C2\C=C1\CC[C@@H](C(=C)C)C[C@@]1(C)[C@H](C)C2
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]
GHS07: Exclamation mark
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).
☒N verify (what is checkY☒N ?)

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]

Production

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

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

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

Uses

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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

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References

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  1. ^ GHS: Sigma-Aldrich 74437 (SDS)
  2. ^ Furusawa, Mai; Toshihiro Hashimoto; Yoshiaki Noma; Yoshinori Asakawa (November 2005). "Highly Efficient Production of Nootkatone, the Grapefruit Aroma from Valencene, by Biotransformation". Chem. Pharm. Bull. 53 (11): 1513–1514. doi:10.1248/cpb.53.1513. PMID 16272746.
  3. ^ "Cupressus nootkatensis / Nootka cypress | Conifer Species".
  4. ^ Horn, Evan J.; Rosen, Brandon R.; Chen, Yong; Tang, Jiaze; Chen, Ke; Eastgate, Martin D.; Baran, Phil S. (2016). "Scalable and sustainable electrochemical allylic C–H oxidation". Nature. 533 (7601): 77–81. Bibcode:2016Natur.533...77H. doi:10.1038/nature17431. PMC 4860034. PMID 27096371.
  5. ^ "Cost effective fermentation replaces costly extraction". Allylix. Archived from the original on 2012-03-25. Retrieved 10 August 2012.
  6. ^ Bigelow, Bruce (2011-04-28). "Nootkatone, So A-peeling in Grapefruit, is Repellent to Mosquitoes and Ticks". xconomy.com. Retrieved 10 August 2012.
  7. ^ Norris, Edmund J.; Gross, Aaron D.; Kimber, Michael J.; Bartholomay, Lyric; Coats, Joel (2018). "Plant Terpenoids Modulate α-Adrenergic Type 1 Octopamine Receptor (PaOA1) Isolated from the American Cockroach (Periplaneta americana)". Advances in the Biorational Control of Medical and Veterinary Pests. ACS Symposium Series. Vol. 1289. pp. 219–235. doi:10.1021/bk-2018-1289.ch012. ISBN 9780841233591.
  8. ^ a b Jan Suszkiw (January 2011). "Lignin + Nootkatone = Dead Ticks". USDA.
  9. ^ a b Dolan, MC.; Jordan, RA.; Schulze, TL.; Schulze, CJ.; Manning, MC.; Ruffolo, D.; Schmidt, JP.; Piesman, J.; Karchesy, JJ. (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. 102 (6): 2316–24. doi:10.1603/029.102.0638. PMID 20069863. S2CID 2731012.
  10. ^ a b Jordan, Robert A.; Schulze, Terry L.; Dolan, Marc C. (January 2012). "Efficacy of Plant-Derived and Synthetic Compounds on Clothing as Repellents Against Ixodes scapularis and Amblyomma americanum (Acari: Ixodidae)" (PDF). Journal of Medical Entomology. 49 (1): 101–106. doi:10.1603/ME10241. PMID 22308777. Archived from the original on June 18, 2017.
  11. ^ Zhu BC, Henderson G, Chen F, Maistrello L, Laine RA (March 2001). "Nootkatone is a repellent for Formosan subterranean termite (Coptotermes formosanus)". J Chem Ecol. 27 (3): 523–31. doi:10.1023/a:1010301308649. PMID 11441443.
  12. ^ a b c d Richard Knox (April 18, 2011). "Repelling Bugs with the Essence of Grapefruit". NPR.
  13. ^ "EPS approves nootkatone". 10 August 2020.
  14. ^ McNeil, Donald G. Jr. (2020-08-11). "Citrus Flavoring Is Weaponized Against Insect-Borne Diseases". nytimes.com. Retrieved 2021-07-05.
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