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nootkatone
4,4a,5,6,7,8-hexahydro-6-isopropenyl-4,4a-dimethyl-2(3H)-naphthalenone

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CAS Number: 91416-23-8Picture of molecule3D/inchi
FDA UNII: Search
Nikkaji Web:J53.411K
XlogP3-AA:3.90 (est)
Molecular Weight:218.33954000
Formula:C15 H22 O
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:flavor and fragrance agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Perfumer and Flavorist:Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 318.00 to 319.00 °C. @ 760.00 mm Hg (est)
Vapor Pressure:0.000358 mmHg @ 25.00 °C. (est)
Flash Point: 288.00 °F. TCC ( 142.10 °C. ) (est)
logP (o/w): 3.765 (est)
Soluble in:
 alcohol
 water, 2.375 mg/L @ 25 °C (est)
Insoluble in:
 water
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Associate Allied Chemicals
Nootkatone
About
 
Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
flavor and fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
 
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :20797
National Institute of Allergy and Infectious Diseases:Data
4,4a-dimethyl-6-prop-1-en-2-yl-3,4,5,6,7,8-hexahydronaphthalen-2-one
Chemidplus:0091416238
 
References:
Leffingwell:Chirality or Article
 4,4a-dimethyl-6-prop-1-en-2-yl-3,4,5,6,7,8-hexahydronaphthalen-2-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):20797
Pubchem (sid):135081658
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
HMDB (The Human Metabolome Database):Search
FooDB:FDB014799
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 grapefruit
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 lemon oil
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 lemon petiole
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 lemon tissue culture
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 lime fruit
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 mandarin fruit
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 orange fruit
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 orange pericarp oil
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Synonyms:
4a,5-dimethyl-1,2,3,4,4a,5,6,7-octahydro-7-keto-3-isopropenylnaphthalene
4,4a-dimethyl-6-prop-1-en-2-yl-3,4,5,6,7,8-hexahydronaphthalen-2-one
5,6-dimethyl-8-isopropenylbicyclo(4.4.0)dec-1-en-3-one
4,4a,5,6,7,8-hexahydro-6-isopropenyl-4,4a-dimethyl-2(3H)-naphthalenone
2(3H)-naphthalenone, 4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-
6-isopropenyl-4,4a-dimethyl-4,4a,5,6,7,8-hexahydro-2(3H)-naphthalenone
 

Articles:

PubMed:Production of the sesquiterpenoid (+)-nootkatone by metabolic engineering of Pichia pastoris.
PubMed:Different accumulation profiles of multiple components between pericarp and seed of Alpinia oxyphylla capsular fruit as determined by UFLC-MS/MS.
PubMed:(+)-Nootkatone inhibits tumor necrosis factor α/interferon γ-induced production of chemokines in HaCaT cells.
PubMed:Valencene oxidase CYP706M1 from Alaska cedar (Callitropsis nootkatensis).
PubMed:Valencene synthase from the heartwood of Nootka cypress (Callitropsis nootkatensis) for biotechnological production of valencene.
PubMed:Modification of valencene by bio- and chemical transformation.
PubMed:Quantitative analysis of the major constituents in Chinese medicinal preparation SuoQuan formulae by ultra fast high performance liquid chromatography/quadrupole tandem mass spectrometry.
PubMed:Ready access to functionally embellished cis-hydrindanes and cis-decalins: protecting group-free total syntheses of (±)-Nootkatone and (±)-Noreremophilane.
PubMed:Anti-diarrheal constituents of Alpinia oxyphylla.
PubMed:Challenges and pitfalls of P450-dependent (+)-valencene bioconversion by Saccharomyces cerevisiae.
PubMed:Compositions of the volatile oils of Citrus macroptera and C. maxima.
PubMed:Characterisation of commercial aromatised vinegars: phenolic compounds, volatile composition and antioxidant activity.
PubMed:Efficacy and environmental persistence of nootkatone for the control of the blacklegged tick (Acari: Ixodidae) in residential landscapes.
PubMed:HPTLC and reverse phase HPLC methods for the simultaneous quantification and in vitro screening of antioxidant potential of isolated sesquiterpenoids from the rhizomes of Cyperus rotundus.
PubMed:Efficacy of plant-derived and synthetic compounds on clothing as repellents against Ixodes scapularis and Amblyomma americanum (Acari: Ixodidae).
PubMed:Experimental use of two standard tick collection methods to evaluate the relative effectiveness of several plant-derived and synthetic repellents against Ixodes scapularis and Amblyomma americanum (Acari: Ixodidae).
PubMed:Functional expression of a valencene dioxygenase from Pleurotus sapidus in E. coli.
PubMed:A formulation to encapsulate nootkatone for tick control.
PubMed:CYP264B1 from Sorangium cellulosum So ce56: a fascinating norisoprenoid and sesquiterpene hydroxylase.
PubMed:A-Z of nutritional supplements: dietary supplements, sports nutrition foods and ergogenic aids for health and performance--Part 27.
PubMed:Toxic effects of Citrus aurantium and C. limon essential oils on Spodoptera frugiperda (Lepidoptera: Noctuidae).
PubMed:(+)-Nootkatone and (+)-valencene from rhizomes of Cyperus rotundus increase survival rates in septic mice due to heme oxygenase-1 induction.
PubMed:Biologically important eremophilane sesquiterpenes from alaska cedar heartwood essential oil and their semi-synthetic derivatives.
PubMed:Suppression of host-seeking Ixodes scapularis and Amblyomma americanum (Acari: Ixodidae) nymphs after dual applications of plant-derived acaricides in New Jersey.
PubMed:Susceptibility of four tick species, Amblyomma americanum, Dermacentor variabilis, Ixodes scapularis, and Rhipicephalus sanguineus (Acari: Ixodidae), to nootkatone from essential oil of grapefruit.
PubMed:Determination of volatile, phenolic, organic acid and sugar components in a Turkish cv. Dortyol (Citrus sinensis L. Osbeck) orange juice.
PubMed:[Study on quality standards of decoction pieces of salt Alpinia].
PubMed:Anti-allergic activity of sesquiterpenes from the rhizomes of Cyperus rotundus.
PubMed:Microbial transformation of (+)-nootkatone and the antiproliferative activity of its metabolites.
PubMed:Antiplatelet effects of Cyperus rotundus and its component (+)-nootkatone.
PubMed:Mode of action for natural products isolated from essential oils of two trees is different from available mosquito adulticides.
PubMed:A chicory cytochrome P450 mono-oxygenase CYP71AV8 for the oxidation of (+)-valencene.
PubMed:Structural requirements for repellency: norsesquiterpenes and sesquiterpenoid derivatives of nootkatone against the Formosan subterranean termite (Isoptera: Rhinotermitidae).
PubMed:Catalytic oxidation of concentrated orange oil phase by synthetic metallic complexes biomimetic to MMO enzyme.
PubMed:Nootkatone, a characteristic constituent of grapefruit, stimulates energy metabolism and prevents diet-induced obesity by activating AMPK.
PubMed:Isolation and purification of nootkatone from the essential oil of fruits of Alpinia oxyphylla Miquel by high-speed counter-current chromatography.
PubMed: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.
PubMed:A dioxygenase of Pleurotus sapidus transforms (+)-valencene regio-specifically to (+)-nootkatone via a stereo-specific allylic hydroperoxidation.
PubMed:Genome mining in Sorangium cellulosum So ce56: identification and characterization of the homologous electron transfer proteins of a myxobacterial cytochrome P450.
PubMed:An efficient and economic asymmetric synthesis of (+)-nootkatone, tetrahydronootkatone, and derivatives.
PubMed:Regioselective biooxidation of (+)-valencene by recombinant E. coli expressing CYP109B1 from Bacillus subtilis in a two-liquid-phase system.
PubMed:Nootkatone--a biotechnological challenge.
PubMed:[GC-MS analysis of volatile constituents from five different kinds of Chinese eaglewood].
PubMed:Biotransformation of terpenoids by mammals, microorganisms, and plant-cultured cells.
PubMed:Repellent activity of fractioned compounds from Chamaecyparis nootkatensis essential oil against nymphal Ixodes scapularis (Acari: Ixodidae).
PubMed:Volatile constituents of redblush grapefruit (Citrus paradisi) and pummelo (Citrus grandis) peel essential oils from Kenya.
PubMed:Changes in heartwood chemistry of dead yellow-cedar trees that remain standing for 80 years or more in southeast Alaska.
PubMed:Highly efficient production of nootkatone, the grapefruit aroma from valencene, by biotransformation.
PubMed:Biotransformation of citrus aromatics nootkatone and valencene by microorganisms.
PubMed:Use of novel compounds for pest control: insecticidal and acaricidal activity of essential oil components from heartwood of Alaska yellow cedar.
PubMed:Bioconversion of (+)-valencene in submerged cultures of the ascomycete Chaetomium globosum.
PubMed:Biotransformation of the sesquiterpene (+)-valencene by cytochrome P450cam and P450BM-3.
PubMed:Toxicity and behavioral effects of nootkatone, 1,10-dihydronootkatone, and tetrahydronootkatone to the formosan subterranean termite (Isoptera: Rhinotermitidae).
PubMed:Structure-activity of valencenoid derivatives and their repellence to the Formosan subterranean termite.
PubMed:Induction of apoptosis by Citrus paradisi essential oil in human leukemic (HL-60) cells.
PubMed: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.
PubMed:The sesquiterpenoid nootkatone and the absolute configuration of a dibromo derivative.
PubMed:[Grapefruit juice and drugs: a hazardous combination?].
PubMed:Comparative effects of vetiver oil, nootkatone and disodium octaborate tetrahydrate on Coptotermes formosanus and its symbiotic fauna.
PubMed: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.
PubMed:Use of nootkatone as a senescence indicator for Rouge La Toma Cv. grapefruit (Citrus paradisi Macf.).
PubMed:Inhibition of acetylcholinesterase activity by essential oil from Citrus paradisi.
PubMed:Aroma composition changes in early season grapefruit juice produced from thermal concentration.
PubMed:Modulation of radioligand binding to the GABA(A)-benzodiazepine receptor complex by a new component from Cyperus rotundus.
PubMed:Efficacy of vetiver oil and nootkatone as soil barriers against Formosan subterranean termite (Isoptera: Rhinotermitidae).
PubMed:Nootkatone is a repellent for Formosan subterranean termite (Coptotermes formosanus).
PubMed:Determination of Key Flavor Components in Methylene Chloride Extracts from Processed Grapefruit Juice.
PubMed:Insecticidal sesquiterpene from Alpinia oxyphylla against Drosophila melanogaster.
PubMed:Inhibition selectivity of grapefruit juice components on human cytochromes P450.
PubMed:Grapefruit gland oil composition is affected by wax application, storage temperature, and storage time.
PubMed:Effect of ethylene on naringin, narirutin and nootkatone accumulation in grapefruit.
PubMed:Accumulation of the sesquiterpenes nootkatone and valencene by callus cultures of Citrus paradisi, Citrus limonia and Citrus aurantium.
PubMed:Anti-ulcer effect in rats of bitter cardamon constituents.
PubMed:Terpenoid biotransformation in mammals. IV Biotransformation of (+)-longifolene, (-)-caryophyllene, (-)-caryophyllene oxide, (-)-cyclocolorenone, (+)-nootkatone, (-)-elemol, (-)-abietic acid and (+)-dehydroabietic acid in rabbits.
PubMed:Regioselective biotransformation of valencene in cell suspension cultures of Citrus sp.
PubMed:In Vivo Protective Effects of Nootkatone against Particles-Induced Lung Injury Caused by Diesel Exhaust Is Mediated via the NF-κB Pathway.
PubMed:Thrombosis, systemic and cardiac oxidative stress and DNA damage induced by pulmonary exposure to diesel exhaust particles, and the effect of nootkatone thereon.
PubMed:Cell-free one-pot conversion of (+)-valencene to (+)-nootkatone by a unique dye-decolorizing peroxidase combined with a laccase from Funalia trogii.
PubMed:Characterization of CYP154F1 from Thermobifida fusca YX and Extension of Its Substrate Spectrum by Site-Directed Mutagenesis.
PubMed:Heterologous Protein Expression in Pichia pastoris: Latest Research Progress and Applications.
PubMed:Nootkatone confers hepatoprotective and anti-fibrotic actions in a murine model of liver fibrosis by suppressing oxidative stress, inflammation, and apoptosis.
PubMed:Neuroprotective effects of nootkatone from Alpiniae oxyphyllae Fructus against amyloid-β-induced cognitive impairment.
PubMed:CYP109E1 is a novel versatile statin and terpene oxidase from Bacillus megaterium.
PubMed:Comparative study of submerged and surface culture acetification process for orange vinegar.
PubMed:Nootkatone encapsulation by cyclodextrins: Effect on water solubility and photostability.
PubMed:Ethanol extract and its dichloromethane fraction of Alpinia oxyphylla Miquel exhibited hepatoprotective effects against CCl4-induced oxidative damage in vitro and in vivo with the involvement of Nrf2.
PubMed:DIURETIC AND ANTI-DIURETIC BIOACTIVITY DIFFERENCES OF THE SEED AND SHELL EXTRACTS OFALPINIA OXYPHYLLAFRUIT.
PubMed:Control of stress-induced depressive disorders by So-ochim-tang-gamibang, a Korean herbal medicine.
PubMed:Cytochromes P450: History, Classes, Catalytic Mechanism, and Industrial Application.
PubMed:Synthetic genome engineering forging new frontiers for wine yeast.
PubMed:Botanical drugs in Ayurveda and Traditional Chinese Medicine.
PubMed:Integrated Analysis of the Wood Oil from Xanthocyparis vietnamensis Farjon & Hiep. by Chromatographic and Spectroscopic Techniques.
PubMed:Enhancing cytochrome P450-mediated conversions in P. pastoris through RAD52 over-expression and optimizing the cultivation conditions.
PubMed:In vitro inhibitory effects of plumbagin, the promising antimalarial candidate, on human cytochrome P450 enzymes.
PubMed:Exchanging ligand-binding specificity between a pair of mouse olfactory receptor paralogs reveals odorant recognition principles.
PubMed:New Sesquiterpene Oxidations with CYP260A1 and CYP264B1 from Sorangium cellulosum So ce56.
PubMed:Bioactivity-guided isolation of anti-hepatitis B virus active sesquiterpenoids from the traditional Chinese medicine: Rhizomes of Cyperus rotundus.
PubMed:GC-FID coupled with chemometrics for quantitative and chemical fingerprinting analysis of Alpinia oxyphylla oil.
PubMed:Izalpinin from fruits of Alpinia oxyphylla with antagonistic activity against the rat bladder contractility.
PubMed:Nootkatone.
PubMed:Evaluation of 89 compounds for identification of substrates for cynomolgus monkey CYP2C76, a new bupropion/nifedipine oxidase.
PubMed:High-throughput functional screening of steroid substrates with wild-type and chimeric P450 enzymes.
PubMed:Crosses between monokaryons of Pleurotus sapidus or Pleurotus florida show an improved biotransformation of (+)-valencene to (+)-nootkatone.
PubMed:Ligand-selective activation of heterologously-expressed mammalian olfactory receptor.
PubMed:Tissue-specific metabolite profiling of Cyperus rotundus L. rhizomes and (+)-nootkatone quantitation by laser microdissection, ultra-high-performance liquid chromatography-quadrupole time-of-flight mass spectrometry, and gas chromatography-mass spectrometry techniques.
PubMed:Identification of known chemicals and their metabolites from Alpinia oxyphylla fruit extract in rat plasma using liquid chromatography/tandem mass spectrometry (LC-MS/MS) with selected reaction monitoring.
PubMed:Isolation and characterization of wild-type lipoxygenase LOX(Psa)1 from Pleurotus sapidus.
PubMed:(+)-Nootkatone inhibits tumor necrosis factor α/interferon γ-induced production of chemokines in HaCaT cells.
 
Notes:
Constit. of grapefruit oil and juice. Flavouring ingredient
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