Nootkatone

Last updated
Nootkatone
Nootkatone crystals Nootkatone recrystallized.jpg
Nootkatone crystals
Nootkatone.svg
(+)-nootkatone-from-xtal-3D-bs-17.png
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 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
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 Yes check.svgY
    Key: WTOYNNBCKUYIKC-JMSVASOKSA-N Yes check.svgY
  • 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
AppearanceClear 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]
GHS-pictogram-exclam.svg
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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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]

Contents

Production

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

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

  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. 1 2 Jan Suszkiw (January 2011). "Lignin + Nootkatone = Dead Ticks". USDA.
  9. 1 2 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. 1 2 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. hdl: 11380/455822 . PMID   11441443.
  12. 1 2 3 4 Richard Knox (April 18, 2011). "Repelling Bugs with the Essence of Grapefruit". NPR .
  13. ↑ "EPA 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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