NOOTKATONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C15H22O
Molecular Weight	218.3346
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@@H]1CC(=O)C=C2CC[C@H](C[C@@]12C)C(C)=C

InChI

InChIKey=WTOYNNBCKUYIKC-JMSVASOKSA-N

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

HIDE SMILES / InChI

Molecular Formula	C15H22O
Molecular Weight	218.3346
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

PubMed

Title	Date	PubMed
Inhibition of acetylcholinesterase activity by essential oil from Citrus paradisi.	2001	11858553
Efficacy of vetiver oil and nootkatone as soil barriers against Formosan subterranean termite (Isoptera: Rhinotermitidae).	2001 Dec	11777060
Nootkatone is a repellent for Formosan subterranean termite (Coptotermes formosanus).	2001 Mar	11441443
Use of nootkatone as a senescence indicator for Rouge La Toma Cv. grapefruit (Citrus paradisi Macf.).	2002 Aug 14	12166965
Aroma composition changes in early season grapefruit juice produced from thermal concentration.	2002 Feb 13	11829649
Modulation of radioligand binding to the GABA(A)-benzodiazepine receptor complex by a new component from Cyperus rotundus.	2002 Jan	11824542
Absolute stereostructures of three new sesquiterpenes from the fruit of Alpinia oxyphylla with inhibitory effects on nitric oxide production and degranulation in RBL-2H3 cells.	2002 Oct	12398545
Structure-activity of valencenoid derivatives and their repellence to the Formosan subterranean termite.	2003 Dec	14969356
Citrus fruit flavor and aroma biosynthesis: isolation, functional characterization, and developmental regulation of Cstps1, a key gene in the production of the sesquiterpene aroma compound valencene.	2003 Dec	14617067
Comparative effects of vetiver oil, nootkatone and disodium octaborate tetrahydrate on Coptotermes formosanus and its symbiotic fauna.	2003 Jan	12558100
The sesquiterpenoid nootkatone and the absolute configuration of a dibromo derivative.	2003 May	12743407
Induction of apoptosis by Citrus paradisi essential oil in human leukemic (HL-60) cells.	2003 Nov-Dec	14758720
Toxicity and behavioral effects of nootkatone, 1,10-dihydronootkatone, and tetrahydronootkatone to the formosan subterranean termite (Isoptera: Rhinotermitidae).	2004 Feb	14998133
Volatile constituents of redblush grapefruit (Citrus paradisi) and pummelo (Citrus grandis) peel essential oils from Kenya.	2005 Dec 14	16332132
Bioconversion of (+)-valencene in submerged cultures of the ascomycete Chaetomium globosum.	2005 Jun	15602686
Use of novel compounds for pest control: insecticidal and acaricidal activity of essential oil components from heartwood of Alaska yellow cedar.	2005 May	15962787
Changes in heartwood chemistry of dead yellow-cedar trees that remain standing for 80 years or more in southeast Alaska.	2005 Nov	16273433
Highly efficient production of nootkatone, the grapefruit aroma from valencene, by biotransformation.	2005 Nov	16272746
Biotransformation of citrus aromatics nootkatone and valencene by microorganisms.	2005 Nov	16272725
Repellent activity of fractioned compounds from Chamaecyparis nootkatensis essential oil against nymphal Ixodes scapularis (Acari: Ixodidae).	2006 Sep	17017233
[GC-MS analysis of volatile constituents from five different kinds of Chinese eaglewood].	2007 May	17727060
Citrus genomics.	2008	18509486
Screening of 397 chemicals and development of a quantitative structure--activity relationship model for androgen receptor antagonism.	2008 Apr	18324785
Induction of multiple pleiotropic drug resistance genes in yeast engineered to produce an increased level of anti-malarial drug precursor, artemisinic acid.	2008 Nov 4	18983675
Toxicity, tunneling and feeding behavior of the termite, Coptotermes vastator, in sand treated with oil of the physic nut, Jatropha curcas.	2009	20053119
An efficient and economic asymmetric synthesis of (+)-nootkatone, tetrahydronootkatone, and derivatives.	2009 Aug 20	19630428
Regioselective biooxidation of (+)-valencene by recombinant E. coli expressing CYP109B1 from Bacillus subtilis in a two-liquid-phase system.	2009 Jul 10	19591681
Nootkatone--a biotechnological challenge.	2009 May	19333595
Genome mining in Sorangium cellulosum So ce56: identification and characterization of the homologous electron transfer proteins of a myxobacterial cytochrome P450.	2009 Oct 16	19696019
Natural toxins for use in pest management.	2010 Aug	22069667
Structural requirements for repellency: norsesquiterpenes and sesquiterpenoid derivatives of nootkatone against the Formosan subterranean termite (Isoptera: Rhinotermitidae).	2010 Aug	20602525
Nootkatone, a characteristic constituent of grapefruit, stimulates energy metabolism and prevents diet-induced obesity by activating AMPK.	2010 Aug	20501876
[Study on quality standards of decoction pieces of salt Alpinia].	2010 Dec	21438389
Catalytic oxidation of concentrated orange oil phase by synthetic metallic complexes biomimetic to MMO enzyme.	2010 Jul	20549797
Mode of action for natural products isolated from essential oils of two trees is different from available mosquito adulticides.	2010 Nov	21175062
The mouse eugenol odorant receptor: structural and functional plasticity of a broadly tuned odorant binding pocket.	2011 Feb 8	21142015

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 21:28:28 GMT 2023` Edited by `admin` on `Fri Dec 15 21:28:28 GMT 2023`
Record UNII	IZ2Y119N4J
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NOOTKATONE

Official Name

English

4,4A,5,6,7,8-HEXAHYDRO-4,4A-DIMETHYL-6-(1-METHYLENE-ETHYL)-2(3H)-NAPHTHALENONE

Common Name

English

NOOTKANONE

Common Name

English

4,4A,5,6,7,8-HEXAHYDRO-6-ISO-PROPENYL-4,4A-DIMETHYL-2(3H)-NAPHTHALENONE

Common Name

English

4.BETA.H,5.ALPHA.-EREMOPHILA-1(10),11-DIEN-2-ONE

Common Name

English

NOOTKATONE [MI]

Common Name

English

NOOTKATONE [FHFI]

Common Name

English

2(3H)-NAPHTHALENONE, 4,4A,5,6,7,8-HEXAHYDRO-4,4A-DIMETHYL-6-(1-METHYLETHENYL)-, (4R,4AS,6R)-

Common Name

English

2(3H)-NAPHTHALENONE, 4,4A,5,6,7,8-HEXAHYDRO-4,4A-DIMETHYL-6-(1-METHYLETHENYL)-, (4R-(4.ALPHA.,4A.ALPHA.,6.BETA.))-

Common Name

English

5,6-DIMETHYL-8-ISOPROPENYL-BICYCLO(4,4,0)-DEC-1-EN-3-ONE

Systematic Name

English

(+)-NOOTKATONE

Common Name

English

FEMA NO. 4941

Code

English

Classification Tree Code System Code

JECFA EVALUATION

NOOTKATONE