nootkatone
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 408778015
| Name = Nootkatone
| ImageFile = Nootkatone recrystallized.jpg
| ImageSize =
| ImageName = Nootkatone crystals
| ImageFile1 = Nootkatone.svg
| ImageSize1 =
| ImageName1 =
| ImageFile2 = (+)-nootkatone-from-xtal-3D-bs-17.png
| IUPACName = 4α,5α-Eremophila-1(10),11-dien-2-one
| SystematicName = (4R,4aS,6R)-4,4a-Dimethyl-6-(prop-1-en-2-yl)-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one
| OtherNames = (+)-nootkatone
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 1064812
| PubChem = 1268142
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C17914
| 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
| InChIKey = WTOYNNBCKUYIKC-JMSVASOKBQ
| SMILES = O=C2\C=C1\CC[C@@H](C(=C)C)C[C@@]1(C)[C@H](C)C2
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 446299
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 81377
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = WTOYNNBCKUYIKC-JMSVASOKSA-N
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 4674-50-4
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = IZ2Y119N4J
| RTECS =
}}
|Section2={{Chembox Properties
| C=15 | H=22 | O=1
| Appearance = Clear or white crystals, impure samples appear as a viscous yellow liquid
| Density = 0.968 g/mL
| Solubility = Insoluble in water, very soluble in ethanol, dichloromethane, ethyl acetate, soluble in hexanes
| MeltingPtC = 36
| BoilingPtC = 170
| pKa =
| pKb =
| Viscosity =
}}
|Section3={{Chembox Structure
| MolShape =
| Coordination =
| CrystalStruct =
| Dipole =
}}
|Section7={{Chembox Hazards
| ExternalSDS =
| MainHazards =
| FlashPt = ~
| FlashPtC = 100
| GHSPictograms = {{GHS07}}
| GHSSignalWord = warning
| HPhrases = {{HPhrases|H317}}
| PPhrases = {{PPhrases|P280}}
| GHS_ref = GHS: [https://www.sigmaaldrich.com/NL/en/product/ALDRICH/74437 Sigma-Aldrich 74437] (SDS)
}}
|Section8={{Chembox Related
| OtherAnions =
| OtherCations =
| OtherCompounds =
| OtherFunction = Valencene
| OtherFunction_label = terpenes
}}
}}
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.{{cite journal | last =Furusawa | first =Mai |author2=Toshihiro Hashimoto |author3=Yoshiaki Noma |author4=Yoshinori Asakawa | title =Highly Efficient Production of Nootkatone, the Grapefruit Aroma from Valencene, by Biotransformation | journal =Chem. Pharm. Bull. | volume =53 | issue =11 | pages =1513–1514 | date =November 2005 | doi =10.1248/cpb.53.1513 | pmid =16272746 | doi-access =free }} 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).{{Cite web|url=https://conifersociety.org/conifers/cupressus-nootkatensis/|title = Cupressus nootkatensis / Nootka cypress | Conifer Species}}
Production
Nootkatone is produced commercially from valencene, another more abundant sesquiterpene.{{cite journal |doi=10.1038/nature17431 |title=Scalable and sustainable electrochemical allylic C–H oxidation |date=2016 |last1=Horn |first1=Evan J. |last2=Rosen |first2=Brandon R. |last3=Chen |first3=Yong |last4=Tang |first4=Jiaze |last5=Chen |first5=Ke |last6=Eastgate |first6=Martin D. |last7=Baran |first7=Phil S. |journal=Nature |volume=533 |issue=7601 |pages=77–81 |pmid=27096371 |pmc=4860034 |bibcode=2016Natur.533...77H }}
File:ValenceneToNootkatone.svg
Allylix (Now Lallemand of Montreal, PQ), developed a fermentation process to nootkatone.{{cite web|title=Cost effective fermentation replaces costly extraction |url=http://www.allylix.com/content/nootkatone|work=Allylix|accessdate=10 August 2012 |url-status=dead |archiveurl=https://web.archive.org/web/20120325001759/http://www.allylix.com/content/nootkatone |archivedate=2012-03-25}}{{cite news|last=Bigelow|first=Bruce|title=Nootkatone, So A-peeling in Grapefruit, is Repellent to Mosquitoes and Ticks|url=http://www.xconomy.com/san-diego/2011/04/28/nootkatone-so-a-peeling-in-grapefruit-is-repellent-to-mosquitoes-and-ticks/|accessdate=10 August 2012|newspaper=xconomy.com|date=2011-04-28}}
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.{{cite book|doi=10.1021/bk-2018-1289.ch012|chapter=Plant Terpenoids Modulate α-Adrenergic Type 1 Octopamine Receptor (PaOA1) Isolated from the American Cockroach (Periplaneta americana)|title=Advances in the Biorational Control of Medical and Veterinary Pests|series=ACS Symposium Series|year=2018|last1=Norris|first1=Edmund J.|last2=Gross|first2=Aaron D.|last3=Kimber|first3=Michael J.|last4=Bartholomay|first4=Lyric|last5=Coats|first5=Joel|volume=1289|pages=219–235|isbn=9780841233591}}
Uses
Nootkatone in spray form is an effective repellent or insecticide against deer ticks{{Cite news |url=http://www.ars.usda.gov/is/AR/archive/jan11/ticks0111.htm |title=Lignin + Nootkatone = Dead Ticks |author=Jan Suszkiw |date=January 2011 |publisher=USDA}}{{Cite journal
| last1 = Jordan | first1 = Robert A.
| last2 = Schulze | first2 = Terry L.
| last3 = Dolan | first3 = Marc C.
| title = Efficacy of Plant-Derived and Synthetic Compounds on Clothing as Repellents Against Ixodes scapularis and Amblyomma americanum (Acari: Ixodidae)
| doi = 10.1603/ME10241
| journal = Journal of Medical Entomology
| volume = 49
| pages = 101–106
| date=January 2012
| pmid = 22308777| pmc =
| issue = 1 | url = https://apps.dtic.mil/sti/pdfs/ADA557262.pdf| archive-url = https://web.archive.org/web/20170618123116/http://www.dtic.mil/get-tr-doc/pdf?AD=ADA557262| url-status = live| archive-date = June 18, 2017| doi-access = free}} and lone star ticks.{{Cite journal | last1 = Dolan | first1 = MC. | last2 = Jordan | first2 = RA. | last3 = Schulze | first3 = TL. | last4 = Schulze | first4 = CJ. | last5 = Manning | first5 = MC. | last6 = Ruffolo | first6 = D. | last7 = Schmidt | first7 = JP. | last8 = Piesman | first8 = J. | last9 = Karchesy | first9 = JJ. | title = 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 | journal = J Econ Entomol | volume = 102 | issue = 6 | pages = 2316–24 |date=Dec 2009 | doi = 10.1603/029.102.0638| pmid = 20069863 | s2cid = 2731012 }} It is also an effective repellent or insecticide against mosquitos, and may repel bed bugs, head lice, Formosan termites,{{cite journal |vauthors=Zhu BC, Henderson G, Chen F, Maistrello L, Laine RA |title=Nootkatone is a repellent for Formosan subterranean termite (Coptotermes formosanus) |journal=J Chem Ecol |volume=27 |issue=3 |pages=523–31 |date=March 2001 |pmid=11441443 |doi=10.1023/a:1010301308649 |url=}} and other insects.{{Cite news |url=https://www.npr.org/2011/04/18/135468567/repelling-bugs-with-the-essence-of-grapefruit |title=Repelling Bugs with the Essence of Grapefruit |author=Richard Knox |date=April 18, 2011 |work=NPR}} It is an environmentally friendly insecticide because it is a volatile essential oil that does not persist in the environment. It was approved by the U.S. EPA for this use on August 10, 2020.{{Cite web|last=|first=|date=10 August 2020|title=EPA approves nootkatone|url=https://www.epa.gov/pesticides/nootkatone-now-registered-epa|access-date=|website=}} 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.{{cite news|last=McNeil|first=Donald G. Jr.|title=Citrus Flavoring Is Weaponized Against Insect-Borne Diseases|url=https://www.nytimes.com/2020/08/10/health/tick-mosquito-repellant-nootkatone.html|accessdate=2021-07-05|newspaper=nytimes.com|date=2020-08-11}} It is nontoxic to humans, is an approved food additive, and is commonly used in foods, cosmetics, and pharmaceuticals. The CDC has licensed patents to two companies to produce an insecticide and an insect repellant.
See also
References
{{reflist}}
External links
- [http://www.leffingwell.com/chirality/nootkatone.htm Description of nootkatone at Leffingwell.com]