nootkatone
4,4a,5,6,7,8-hexahydro-6-isopropenyl-4,4a-dimethyl-2(3H)-naphthalenone
Identification
| Name | nootkatone |
| CAS Number | 91416-23-8 |
| FDA UNII | Search |
| Molecular Formula | C15 H22 O |
| Molecular Weight | 218.33954000 |
| Nikkaji Number | J53.411K |
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 Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | flavor and fragrance agents |
| RIFM Fragrance Material Safety Assessment | Search |
Associate Allied Chemicals
Quality, Service and Values
Our aim is to become a reliable one-stop shop for our customers.
Potential Uses
Natural Occurrence
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 Soâce56.
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.