alpha-thujone
bicyclo[3.1.0]hexan-3-one, 4-methyl-1- (1-methylethyl)-, [1S-(1a,4a,5a)]-
Identification
| Name | alpha-thujone |
| CAS Number | 546-80-5 |
| EINECS | 208-912-2 |
| FDA UNII | R0SQ9G0DU5 |
| Molecular Formula | C10 H16 O |
| Molecular Weight | 152.23672000 |
| MDL Number | MFCD00135597 |
| Nikkaji Number | J6.432G |
| Beilstein | 4660369 |
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
| CosIng | cosmetic data |
| Cosmetic Uses | perfuming agents |
Organoleptic Properties
| Odor Description | at 10.00 % in dipropylene glycol. |
Safety Information
| Preferred SDS | View |
| European information | Most important hazard(s): |
| Oral/Parenteral Toxicity | oral-rat LD50 500 mg/kg |
| Dermal Toxicity | subcutaneous-rabbit LD50 362 mg/kg |
| 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 | fragrance agents |
| RIFM Fragrance Material Safety Assessment | Search |
| IFRA Critical Effect | Neurotoxicity |
| IFRA RESTRICTION LIMITS IN THE FINISHED PRODUCT (%) | Category 1: Products applied to the lips |
| Notes | IFRA FLAVOR REQUIREMENTS: |
| Recommendation for alpha-thujone flavor usage levels up to | not for flavor use. |
Penta International Corporation
Chemistry innovation
At Penta, our products and services help businesses do business better.
Potential Uses
Natural Occurrence
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.