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Category:flavor and fragrance agents
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Assay: | 95.00 to 100.00
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| Food Chemicals Codex Listed: | No |
| Boiling Point: | 318.00 to 319.00 °C. @ 760.00 mm Hg (est)
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| Vapor Pressure: | 0.000358 mmHg @ 25.00 °C. (est) |
| Flash Point: | 288.00 °F. TCC ( 142.10 °C. ) (est)
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| 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:
Suppliers:
Safety Information:
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| Hazards identification |
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| Classification of the substance or mixture |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
| None found. |
| GHS Label elements, including precautionary statements |
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| Pictogram | |
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| Hazard statement(s) |
| None found. |
| Precautionary statement(s) |
| None found. |
| Oral/Parenteral Toxicity: |
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Not determined
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| Dermal Toxicity: |
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Not determined
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| Inhalation Toxicity: |
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Not determined
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Safety in Use Information:
Safety References:
References:
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
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 |
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. |
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