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Revision as of 13:07, 19 January 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,074 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: ChEMBL KEGG.← Previous edit Latest revision as of 17:54, 21 May 2024 edit undoMagikMike (talk | contribs)1 editm →Production: Evolva was purchased by Lallemand in 12/23Tag: Visual edit 
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{{chembox {{chembox
| Verifiedfields = changed
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 400330361 | verifiedrevid = 408778015
| Name = Nootkatone | Name = Nootkatone
| ImageFile = Nootkatone.png | ImageFile = Nootkatone recrystallized.jpg
<!-- | ImageSize = 200px --> | ImageSize =
| ImageName = | ImageName = Nootkatone crystals
| ImageFile1 = Nootkatone.svg
| IUPACName = 4-alpha,5-dimethyl-1,2,3,4,4alpha,5,6,7-<br />octahydro-7-keto-3-isopropenylnaphthalene
| ImageSize1 =
⚫ | OtherNames = (+)-nootkatone
| ImageName1 =
⚫ | Section1 = {{Chembox Identifiers
| ImageFile2 = (+)-nootkatone-from-xtal-3D-bs-17.png
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| IUPACName = 4α,5α-Eremophila-1(10),11-dien-2-one
| SystematicName = (4''R'',4a''S'',6''R'')-4,4a-Dimethyl-6-(prop-1-en-2-yl)-4,4a,5,6,7,8-hexahydronaphthalen-2(3''H'')-one
⚫ | OtherNames = (+)-nootkatone
⚫ |Section1={{Chembox Identifiers
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 1064812 | ChemSpiderID = 1064812
| PubChem = 1268142 | PubChem = 1268142
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C17914 | 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 | 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 | InChIKey = WTOYNNBCKUYIKC-JMSVASOKBQ
| SMILES = O=C2\C=C1\CC(C(=C)C)C1(C)(C)C2 | SMILES = O=C2\C=C1\CC(C(=C)C)C1(C)(C)C2
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 446299 | ChEMBL = 446299
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 81377
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | 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 | 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_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = WTOYNNBCKUYIKC-JMSVASOKSA-N | StdInChIKey = WTOYNNBCKUYIKC-JMSVASOKSA-N
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 4674-50-4 | CASNo = 4674-50-4
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | RTECS =
| UNII = IZ2Y119N4J
⚫ | RTECS =
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=15 | H=22 | O=1
| Formula = C<sub>15</sub>H<sub>22</sub>O
| Appearance = Clear or white crystals, impure samples appear as a viscous yellow liquid
| MolarMass = 218.55 g/mol
⚫ | Density = 0.968 g/mL
| Appearance = Viscous yellow in its liquid form
| Solubility = Insoluble in water, very soluble in ethanol, dichloromethane, ethyl acetate, soluble in hexanes
⚫ | Density =
| Solubility = | MeltingPtC = 36
| BoilingPtC = 170
| MeltingPt = 36°C (309 K)
| pKa =
| BoilingPt = 170°C (443 K)
| pKa = | pKb =
| pKb = | Viscosity =
| Viscosity =
}} }}
| Section3 = {{Chembox Structure |Section3={{Chembox Structure
| MolShape = | MolShape =
| Coordination = | Coordination =
| CrystalStruct = | CrystalStruct =
| Dipole = | Dipole =
}} }}
| Section7 = {{Chembox Hazards |Section7={{Chembox Hazards
| ExternalMSDS = | ExternalSDS =
| MainHazards = | MainHazards =
| FlashPt = ~ 100°C | FlashPt = ~
| RPhrases = | FlashPtC = 100
| GHSPictograms = {{GHS07}}
| SPhrases = 23, 24, 25
| GHSSignalWord = warning
| HPhrases = {{HPhrases|H317}}
| PPhrases = {{PPhrases|P280}}
| GHS_ref = <ref>GHS: (SDS)</ref>
}} }}
| Section8 = {{Chembox Related |Section8={{Chembox Related
| OtherAnions = | OtherAnions =
| OtherCations = | OtherCations =
| OtherCompounds =
| Related ]s
| ] | OtherFunction = ]
| OtherFunction_label = ]s
| OtherCpds =
}} }}
}} }}


'''Nootkatone''' is an ], a ], which means that it is a C15 derivative that also contains an oxygen-containing ] (a ]). It is the most valuable ] of ].<ref>{{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 }}</ref> Nootkatone was originally isolated from the wood of the ], ''Cupressus nootkatensis''. The species name, nootkatensis, is derived from the language of the ] people of Canada (formerly referred to as the Nootka people).<ref>{{Cite web|url=https://conifersociety.org/conifers/cupressus-nootkatensis/|title = Cupressus nootkatensis / Nootka cypress &#124; Conifer Species}}</ref>
'''Nootkatone''' is a natural ] and is the most important and expensive aromatic
of ]<ref>{{cite journal
| last =Furusawa
| first =Mai
| authorlink =
| coauthors =Toshihiro Hashimoto, Yoshiaki Noma, and 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
| publisher =
| location =
| date =November 2005
| url =
| doi =10.1248/cpb.53.1513
| id =
| accessdate =
| pmid =16272746 }}</ref>
. It is a ] and a ].


==Production ==
Nootkatone was previously thought to be one of the main chemical components of the smell and flavour of ]s. In its solid form it is usually found as ]s. As a ], it is ] and ]. Nootkatone is typically extracted from ], but can also be manufactured with ], or through the chemical or biochemical ] of ].
Nootkatone is produced commercially from valencene, another more abundant sesquiterpene.<ref>{{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 }}</ref>
Nootkatone encapsulated with ] in a spray has been shown as an effective repellent against deer ticks that carry ] <ref>http://www.ars.usda.gov/is/pr/2011/110112.htm</ref>.
]
Allylix (Now Lallemand of Montreal, PQ), developed a fermentation process to nootkatone.<ref name=AllylixSite>{{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}}</ref><ref name=xconomy2011>{{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}}</ref>


==See also== ==Mechanism of action==
As is true of other plant terpenoids, nootkatone activates α-adrenergic type 1 ] receptor (PaOA1) in susceptible ], causing fatal spasms.<ref>{{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}}</ref>
⚫ *]


==References== ==Uses==
Nootkatone in spray form is an effective repellent or ] against ]<ref name="USDA2011">{{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}}</ref><ref name="Dolan2009"/><ref name="Jordan et al 2012">{{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}}</ref> and ].<ref name="Dolan2009">{{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 }}</ref><ref name="Jordan et al 2012"/> It is also an effective repellent or insecticide against mosquitos, and may repel bed bugs, head lice, ]s,<ref name="pmid11441443">{{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=}}</ref> and other insects.<ref name="NPR2001">{{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=]}}</ref> It is an environmentally friendly insecticide because it is a volatile essential oil that does not persist in the environment.<ref name="NPR2001"/> It was approved by the U.S. EPA for this use on August 10, 2020.<ref>{{Cite web|last=|first=|date=10 August 2020|title=EPS approves nootkatone|url=https://www.epa.gov/pesticides/nootkatone-now-registered-epa|access-date=|website=}}</ref> 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.<ref>{{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}}</ref> It is nontoxic to humans, is an approved food additive,<ref name="NPR2001"/> and is commonly used in foods, cosmetics, and pharmaceuticals.<ref name="USDA2011"/> The ] has licensed patents to two companies to produce an insecticide and an insect repellant.<ref name=NPR2001 />

== See also ==
⚫ * ]

== References ==
{{reflist}} {{reflist}}


==External links== == External links ==
* *


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{{aromatic-stub}}
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