alpha-thujone

bicyclo[3.1.0]hexan-3-one, 4-methyl-1- (1-methylethyl)-, [1S-(1a,4a,5a)]-

CAS: 546-80-5 C10 H16 O MW: 152.23672000 thujonic

Identification

Namealpha-thujone
CAS Number546-80-5
EINECS208-912-2
FDA UNIIR0SQ9G0DU5
Molecular FormulaC10 H16 O
Molecular Weight152.23672000
MDL NumberMFCD00135597
Nikkaji NumberJ6.432G
Beilstein4660369

Regulatory

Physical Properties

Appearance colorless to pale yellow clear liquid (est)
Assay 96.00 to 100.00
Food Chemicals Codex Listed No
Specific Gravity 0.91400 @ 20.00 °C.
Refractive Index 1.45000 @ 20.00 °C.
Boiling Point 200.00 to 201.00 °C. @ 760.00 mm Hg
Vapor Pressure 0.323000 mmHg @ 25.00 °C. (est)
Flash Point 147.00 °F. TCC ( 63.89 °C. )
logP (o/w) 2.044 (est)
Shelf Life 12.00 month(s) or longer if stored properly.
Storage refrigerate in tightly sealed containers.
Soluble in alcohol
Insoluble in water

Cosmetic Information

CosIngcosmetic data
Cosmetic Usesperfuming agents

Organoleptic Properties

Odor Description at 10.00 % in dipropylene glycol.

Safety Information

Preferred SDSView
European informationMost important hazard(s):
Oral/Parenteral Toxicityoral-rat LD50 500 mg/kg
Dermal Toxicitysubcutaneous-rabbit LD50 362 mg/kg
Inhalation ToxicityNot determined

GHS Classification

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

Safety in Use

Categoryfragrance agents
RIFM Fragrance Material Safety AssessmentSearch
IFRA Critical EffectNeurotoxicity
IFRA RESTRICTION LIMITS IN THE FINISHED PRODUCT (%)Category 1: Products applied to the lips
NotesIFRA FLAVOR REQUIREMENTS:
Recommendation for alpha-thujone flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

armoise oil morocco @ 23.9% Data artemisia campestris spp. glutinosa flower oil italy @ trace% Data artemisia gypsacea krasch. oil iran @ 8.90% Data basil plant bay leaf oil anise @ 0.1% Data boldus leaf oil chile @ 14.30% Data caraway seed cascarilla bark oil @ 0.14% Data cayenne fruit cedarleaf oil canada @ 43.90-56.70% Data chamomile sweet false chamomile plant cornmint plant costmary oil @ 0.78% Data cymbopogon citratus (dc.) stapf. oil cuba @ 0.20% Data hyssop oil CO2 extract @ 0.1% Data hyssop shoot layana oil wild zimbabwe @ 1.00-2.90% Data layana oil zimbabwe @ 0.7% Data lemon verbena oil morocco @ 0.3% Data mugwort plant nepeta denudata benth. oil iran @ 0.40% Data nepeta racemosa lam. oil iran @ 0.50% Data oregano plant oregano shoot peppermint oil rosemary plant rosemary sap sage leaf sage leaf oil sage oil sage oil albania @ 35.90% Data sage oil cuba @ 12.95% Data sage oil dalmatian @ 23.00% Data sage oil dalmatian @ 36.00% Data sage oil dalmatian @ 63.30% Data sage oil england @ 24.70% Data sage oil france @ 65.50% Data sage oil germany @ 7.21% Data sage oil hydrodistillation france @ 22.80% Data sage oil lithuania @ 19.58% Data sage oil reunion @ 45.50% Data sage oil sardinia @ 23.00% Data sage oil spain @ 26.50% Data sage plant salvia officinalis oil cuba @ 12.95% Data salvia officinalis oil reunion @ 33.25% Data salvia officinalis seed oil tunisia @ 14.77% Data salvia verbenaca seed oil tunisia @ 0.52% Data savory summer savory plant savory winter savory plant tagete oil CO2 extract @ 0.24% Data tansy flower oil dutch @ 0.70% Data tansy leaf oil dutch @ 0.90% Data tansy oil argentina @ 0.76% Data tansy oil canada @ 0.90% Data tansy oil marocco @ 0.10% Data tarragon leaf oil tarragon shoot thyme oil red spain @ 0.00-0.51% Data wormwood oil america @ 3.42% Data wormwood oil italy @ 67.5% Data wormwood oil poland @ 8.03% Data yarrow oil greece @ 1.50% Data

Synonyms

bicyclo(3.1.0)hexan-3-one, 4-methyl-1-(1-methylethyl)-, (1S,4R,5R)- bicyclo[3.1.0]hexan-3-one, 4-methyl-1- (1-methylethyl)-, [1S-(1a,4a,5a)]- bicyclo[3.1.0]hexan-3-one, 4-methyl-1-(1-methylethyl)-, (1S,4R,5R)- (1S-1-alpha, 4-alpha,5-alpha)-4- methyl-1-(1-methyl ethyl) bicyclo(3.1.0)hexan-3-one (1S,4R,5R)-4- methyl-1-(1-methylethyl)bicyclo[3.1.0]hexan-3-one [1S-(1a,4a,5a)]-4- methyl-1-(1-methylethyl)bicyclo[3.1.0]hexan-3-one (1S,4R,5R)-4-1S,4R,5R)-4- methyl-1-(propan-2-yl)bicyclo[3.1.0]hexan-3-one (1S,4R,5R)-4- methyl-1-propan-2-ylbicyclo[3.1.0]hexan-3-one iso propyl methyl bicyclohexanone (1S,4R)-1-iso propyl-4-methyl bicyclo(3.1.0)hexan-3-one (Z+E)-1-iso propyl-4-methyl bicyclo(3.1.0)hexan-3-one (1S,4R,5R)-1-iso propyl-4-methylbicyclo[3.1.0]hexan-3-one (1S,4R)-1-iso propyl-4-methylbicyclo[3.1.0]hexan-3-one (1S,4R,5R)- thujan-3-one (-)-3- thujanone (1S,4R,5R)-(-)-3- thujanone 3- thujanone, (-)- 3- thujanone, (1S,4R,5R)-(-)- (-)- thujone (-)-3-iso thujone (-)-a- thujone (-)-alpha- thujone (-)-iso thujone a- thujone a-(-)- thujone alpha- thujone L- thujone laevo- thujone PubMed: Chemical composition and antimicrobial activity of essential oils from Acantholippia deserticola, Artemisia proceriformis, Achillea micrantha and Libanotis buchtormensis against phytopathogenic bacteria and fungi. PubMed: Attenuated Total Reflectance-Fourier Transform Infrared Spectroscopy on Intact Dried Leaves of Sage (Salvia officinalis L.): Accelerated Chemotaxonomic Discrimination and Analysis of Essential Oil Composition. PubMed: Determination of volatile organic compounds in the dried leaves of Salvia species by solid-phase microextraction coupled to gas chromatography mass spectrometry. PubMed: Artemisia herba-alba essential oil from Buseirah (south Jordan): Chemical characterization and assessment of safe antifungal and anti-inflammatory doses. PubMed: Repellent Effect and Metabolite Volatile Profile of the Essential Oil of Achillea millefolium Against Aegorhinus nodipennis (Hope) (Coleoptera: Curculionidae). PubMed: Ethnobotanical survey of medicinal plants used in the Maseru district of Lesotho. PubMed: Artemisia arborescens "Powis Castle" extracts and α-thujone prevent fruit infestation by codling moth neonates. PubMed: Thuja occidentalis L. and its active compound, α-thujone: Promising effects in the treatment of polycystic ovary syndrome without inducing osteoporosis. PubMed: The antifungal activity of Artemisia sieberi essential oil from different localities of Iran against dermatophyte fungi. PubMed: Inhibitory Effects of Chrysanthemum boreale Essential Oil on Biofilm Formation and Virulence Factor Expression of Streptococcus mutans. PubMed: Fumigant toxicity of basil oil compounds and related compounds to Thrips palmi and Orius strigicollis. PubMed: Volatile compounds from Achillea tenorii (Grande) growing in the Majella National Park (Italy). PubMed: Volatile-oils composition, and bioactivity of the essential oils of Plectranthus barbatus, P. neochilus, and P. ornatus grown in Portugal. PubMed: TLC-direct bioautography for determination of antibacterial activity of Artemisia adamsii essential oil. PubMed: Central α- and β-thujone: similar anxiogenic-like effects and differential modulation on GABAA receptors in neonatal chicks. PubMed: Chemical composition and general toxicity of essential oils extracted from the aerial parts of Artemisia armeniaca Lam. and A. incana (L.) Druce growing in Iran. PubMed: Toxicokinetics of α-thujone following intravenous and gavage administration of α-thujone or α- and β-thujone mixture in male and female F344/N rats and B6C3F1 mice. PubMed: Phytochemical composition of the essential oil of different populations of Stachys lavandulifolia Vahl. PubMed: Constituents of Artemisia gmelinii Weber ex Stechm. from Uttarakhand Himalaya: A Source of Artemisia Ketone. PubMed: Bioactivities of volatile components from Nepalese Artemisia species. PubMed: Identification of genes in Thuja plicata foliar terpenoid defenses. PubMed: Attempts to separate (-)-α-thujone, (+)-β-thujone epimers from camphor enantiomers by enantioselective HPLC with polarimetric detection. PubMed: Monoterpene α-thujone exerts a differential inhibitory action on GABA(A) receptors implicated in phasic and tonic GABAergic inhibition. PubMed: Chemical composition and anticancer activity of essential oils of Mediterranean sage (Salvia officinalis L.) grown in different environmental conditions. PubMed: Terpenoids of plant origin inhibit morphogenesis, adhesion, and biofilm formation by Candida albicans. PubMed: Essential oil variation in the populations of Artemisia spicigera from northwest of Iran: chemical composition and antibacterial activity. PubMed: Chemical composition and antimicrobial activity of essential oils from Scabiosa arenaria Forssk: growing wild in Tunisia. PubMed: Modulation of GABAergic synaptic currents and current responses by α-thujone and dihydroumbellulone. PubMed: Chemical composition and antifungal activity of Artemisia nilagirica essential oil growing in northern hilly areas of India. PubMed: Metabolism of α-thujone in human hepatic preparations in vitro. PubMed: Composition and intraspecific chemical variability of the essential oil from Artemisia herba-alba growing wild in a Tunisian arid zone. PubMed: Antimicrobial and antioxidant properties of the essential oil of Salvia lanigera from Cyprus. PubMed: Chemical composition of the essential oil of Salvia officinalis L. from Romania. PubMed: Effects of foliar fertilization and arbuscular mycorrhizal colonization on Salvia officinalis L. growth, antioxidant capacity, and essential oil composition. PubMed: Composition at different development stages of the essential oil of four Achillea species grown in Iran. PubMed: Essential oil composition of Achillea clusiana from Bulgaria. PubMed: Misidentification of tansy, Tanacetum macrophyllum, as yarrow, Achillea grandifolia: a health risk or benefit? PubMed: Influence of gibberellin and daminozide on the expression of terpene synthases and on monoterpenes in common sage (Salvia officinalis). PubMed: Artemisia fukudo essential oil attenuates LPS-induced inflammation by suppressing NF-kappaB and MAPK activation in RAW 264.7 macrophages. PubMed: Chemical composition of hydrodistilled essential oil of Artemisia incana (L.) Druce and antimicrobial activity against foodborne microorganisms. PubMed: Variations in essential oil, phenolic compounds, and antioxidant activity of tunisian cultivated Salvia officinalis L. PubMed: Absinthe, epileptic seizures and Valentin Magnan. PubMed: Compositional variation of the essential oils of Artemisia afra Jacq. from three provinces in South Africa--a case study of its safety. PubMed: In vitro evaluation of the permeation through reconstructed human epidermis of essentials oils from cosmetic formulations. PubMed: Essential oil composition of Tanacetum vulgare subsp. siculum (Guss.) Raimondo et Spadaro (Asteraceae) from Sicily. PubMed: Flowerhead volatile oil composition of soilless culture-grown Chrysanthemum balsamita L. PubMed: Cytotoxicity, antimicrobial activity and composition of essential oil from Tanacetum balsamita L. subsp. balsamita. PubMed: Effects of the essential oils of Lippia turbinata and Lippia polystachya (Verbenaceae) on the temporal pattern of locomotion of the mosquito Culex quinquefasciatus (Diptera: Culicidae) larvae. PubMed: Tunisian Salvia officinalis L. and Schinus molle L. essential oils: their chemical compositions and their preservative effects against Salmonella inoculated in minced beef meat. PubMed: Mass propagation and essential oil analysis of Artemisia vulgaris. PubMed: Tick repellent substances in the essential oil of Tanacetum vulgare. PubMed: Chemical composition and antibacterial activity of essential oil from Artemisia feddei. PubMed: Insecticidal properties of essential oils from Lippia turbinata and Lippia polystachya (Verbenaceae) against Culex quinquefasciatus (Diptera: Culicidae). PubMed: Composition of the essential oil of Salvia officinalis L. from various European countries. PubMed: Chemical composition and antifungal activity of the essential oils of three species of Artemisia on some soil-borne phytopathogens. PubMed: Comparison of three lychee cultivar odor profiles using gas chromatography-olfactometry and gas chromatography-sulfur detection. PubMed: The essential oil of Solvia cabulica. PubMed: Biotransformation of terpenoids by mammals, microorganisms, and plant-cultured cells. PubMed: Phytochemical analysis of the essential oil of Achillea millefolium L. from various European Countries. PubMed: Acaricidal activities of paeonol and benzoic acid from Paeonia suffruticosa root bark and monoterpenoids against Tyrophagus putrescentiae (Acari: Acaridae). PubMed: Radical intermediates in the catalytic oxidation of hydrocarbons by bacterial and human cytochrome P450 enzymes. PubMed: Chemical composition and antioxidant, antimicrobial, and antifungal activities of the essential oil of Achillea ligustica all. PubMed: Vapor phase toxicity of marjoram oil compounds and their related monoterpenoids to Blattella germanica (Orthoptera: Blattellidae). PubMed: Antiviral activities of extracts and selected pure constituents of Ocimum basilicum. PubMed: Radical rebound mechanism in cytochrome P-450-catalyzed hydroxylation of the multifaceted radical clocks alpha- and beta-thujone. PubMed: The human taste receptor hTAS2R14 responds to a variety of different bitter compounds. PubMed: Antimicrobial activity of Artemisia douglasiana leaf essential oil. PubMed: Chemotypical variation of tansy (Tanacetum vulgare L.) from 40 different locations in Norway. PubMed: Alpha-thujone reduces 5-HT3 receptor activity by an effect on the agonist-reduced desensitization. PubMed: GC analysis of essential oils in the rumen fluid after incubation of Thuja orientalis twigs in the Rusitec system. PubMed: Volatile metabolites from Salvia fruticosa as antifungal agents in soilborne pathogens. PubMed: Antibacterial activity and chemical composition of essential oil of Chrysanthemum boreale. PubMed: Composition and antimicrobial activity of the essential oil of Achillea multifida. PubMed: Organ- and season-dependent variation in the essential oil composition of Salvia officinalis L. cultivated at two different sites. PubMed: Detoxification of alpha- and beta-Thujones (the active ingredients of absinthe): site specificity and species differences in cytochrome P450 oxidation in vitro and in vivo. PubMed: Production of yarrow (Achillea millefolium L.) in Norway: essential oil content and quality. PubMed: Role of human GABA(A) receptor beta3 subunit in insecticide toxicity. PubMed: alpha- and beta-Thujones (herbal medicines and food additives): synthesis and analysis of hydroxy and dehydro metabolites. PubMed: Volatile chemicals identified in extracts from leaves of Japanese mugwort (Artemisia princeps pamp.). PubMed: Composition of essential oil of costmary [Balsamita major (L.) Desf. ] at different growth phases. PubMed: Alpha-thujone (the active component of absinthe): gamma-aminobutyric acid type A receptor modulation and metabolic detoxification. PubMed: Dynamics of yield components and essential oil production in a commercial hybrid sage (Salvia officinalis x Salvia fruticosa cv. Newe Ya'ar no. 4). PubMed: Floral volatiles ofTanacetum vulgare L. attractive toLobesia botrana den. et schiff. females. PubMed: Olfactory responses of a specialist and a generalist grasshopper to volatiles ofArtemisia ludoviciana nutt. (Asteraceae). PubMed: Constituents of the Essential Oil of Artemisia coerulescens.