Identification

Namenootkatone
CAS Number91416-23-8
FDA UNIISearch
Molecular FormulaC15 H22 O
Molecular Weight218.33954000
Nikkaji NumberJ53.411K

Regulatory

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
Insoluble in water

No sensory data available

Safety Information

Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categoryflavor and fragrance agents
RIFM Fragrance Material Safety AssessmentSearch

Associate Allied Chemicals

Quality, Service and Values

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Potential Uses

None Found

Natural Occurrence

grapefruit lemon oil lemon petiole lemon tissue culture lime fruit mandarin fruit orange fruit orange pericarp oil

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-iso propenyl-4,4a-dimethyl-4,4a,5,6,7,8-hexahydro-2(3H)-naphthalenone 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 CCl -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 OF ALPINIA OXYPHYLLA FRUIT. 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.