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
The mouse eugenol odorant receptor: structural and functional plasticity of a broadly tuned odorant binding pocket.	2011-02-08	21142015
[Study on quality standards of decoction pieces of salt Alpinia].	2010-12	21438389
Mode of action for natural products isolated from essential oils of two trees is different from available mosquito adulticides.	2010-11	21175062
Natural toxins for use in pest management.	2010-08	22069667
Structural requirements for repellency: norsesquiterpenes and sesquiterpenoid derivatives of nootkatone against the Formosan subterranean termite (Isoptera: Rhinotermitidae).	2010-08	20602525
Nootkatone, a characteristic constituent of grapefruit, stimulates energy metabolism and prevents diet-induced obesity by activating AMPK.	2010-08	20501876
Catalytic oxidation of concentrated orange oil phase by synthetic metallic complexes biomimetic to MMO enzyme.	2010-07	20549797
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.	2009-12	20069863
Genome mining in Sorangium cellulosum So ce56: identification and characterization of the homologous electron transfer proteins of a myxobacterial cytochrome P450.	2009-10-16	19696019
An efficient and economic asymmetric synthesis of (+)-nootkatone, tetrahydronootkatone, and derivatives.	2009-08-20	19630428
Regioselective biooxidation of (+)-valencene by recombinant E. coli expressing CYP109B1 from Bacillus subtilis in a two-liquid-phase system.	2009-07-10	19591681
Nootkatone--a biotechnological challenge.	2009-05	19333595
Toxicity, tunneling and feeding behavior of the termite, Coptotermes vastator, in sand treated with oil of the physic nut, Jatropha curcas.	2009	20053119
Induction of multiple pleiotropic drug resistance genes in yeast engineered to produce an increased level of anti-malarial drug precursor, artemisinic acid.	2008-11-04	18983675
Screening of 397 chemicals and development of a quantitative structure--activity relationship model for androgen receptor antagonism.	2008-04	18324785
Citrus genomics.	2008	18509486
[GC-MS analysis of volatile constituents from five different kinds of Chinese eaglewood].	2007-05	17727060
Repellent activity of fractioned compounds from Chamaecyparis nootkatensis essential oil against nymphal Ixodes scapularis (Acari: Ixodidae).	2006-09	17017233
Volatile constituents of redblush grapefruit (Citrus paradisi) and pummelo (Citrus grandis) peel essential oils from Kenya.	2005-12-14	16332132
Changes in heartwood chemistry of dead yellow-cedar trees that remain standing for 80 years or more in southeast Alaska.	2005-11	16273433
Highly efficient production of nootkatone, the grapefruit aroma from valencene, by biotransformation.	2005-11	16272746
Biotransformation of citrus aromatics nootkatone and valencene by microorganisms.	2005-11	16272725
Bioconversion of (+)-valencene in submerged cultures of the ascomycete Chaetomium globosum.	2005-06	15602686
Use of novel compounds for pest control: insecticidal and acaricidal activity of essential oil components from heartwood of Alaska yellow cedar.	2005-05	15962787
Induction of apoptosis by Citrus paradisi essential oil in human leukemic (HL-60) cells.	2004-02-05	14758720
Toxicity and behavioral effects of nootkatone, 1,10-dihydronootkatone, and tetrahydronootkatone to the formosan subterranean termite (Isoptera: Rhinotermitidae).	2004-02	14998133
Structure-activity of valencenoid derivatives and their repellence to the Formosan subterranean termite.	2003-12	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.	2003-12	14617067
The sesquiterpenoid nootkatone and the absolute configuration of a dibromo derivative.	2003-05	12743407
Comparative effects of vetiver oil, nootkatone and disodium octaborate tetrahydrate on Coptotermes formosanus and its symbiotic fauna.	2003-01	12558100
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.	2002-10	12398545
Use of nootkatone as a senescence indicator for Rouge La Toma Cv. grapefruit (Citrus paradisi Macf.).	2002-08-14	12166965
Aroma composition changes in early season grapefruit juice produced from thermal concentration.	2002-02-13	11829649
Modulation of radioligand binding to the GABA(A)-benzodiazepine receptor complex by a new component from Cyperus rotundus.	2002-01	11824542
Efficacy of vetiver oil and nootkatone as soil barriers against Formosan subterranean termite (Isoptera: Rhinotermitidae).	2001-12	11777060
Nootkatone is a repellent for Formosan subterranean termite (Coptotermes formosanus).	2001-03	11441443
Inhibition of acetylcholinesterase activity by essential oil from Citrus paradisi.	2001	11858553

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 20:19:36 GMT 2025` Edited by `admin` on `Mon Mar 31 20:19:36 GMT 2025`
Record UNII	IZ2Y119N4J
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NOOTKATONE

Official Name

English

FEMA NO. 4941

Preferred 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

Classification Tree Code System Code

JECFA EVALUATION

NOOTKATONE