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beta-thujone

Chemical Structure

General Material Information

Preferred name beta-thujone
Trivial Name 3-Thujanone
Short Description bicyclo(3.1.0)hexan-3-one, 4-methyl-1-(1-methylethyl)-
Formula C10 H16 O
CAS Number 1125-12-8
ECHA Number 214-405-7
FDA UNII 3110787XAY
Nikkaji Number J138.260H
Beilstein Number 4660369
xLogP3-AA 2.30 (est)
NMR Predictor External link
Synonyms
  • absinthone
  • bicyclo(3.1.0)hexan-3-one, 4-methyl-1-(1-methylethyl)-
  • bicyclo[3.1.0]hexan-3-one, 4-methyl-1-(1-methylethyl)-
  • chrysanthone
  • 4-methyl-1-(1-methyl ethyl) bicyclo(3.1.0)hexan-3-one
  • 4-methyl-1-(propan-2-yl)bicyclo[3.1.0]hexan-3-one
  • 4-methyl-1-propan-2-ylbicyclo[3.1.0]hexan-3-one
  • 1-iso propyl-4-methyl bicyclo(3.1.0)hexan-3-one
  • 1-iso propyl-4-methylbicyclo(3.1.0)hexan-3-one
  • 1-iso propyl-4-methylbicyclo[3.1.0]hexan-3-one
  • 3-sabinanone
  • salvone
  • tanacetone
  • 3-thujanone
  • 4-methyl-1-propan-2-ylbicyclo[3.1.0]hexan-3-one
  • 3-Thujanone
  • 4-Methyl-1-(1-methylethyl)bicyclo[3.1.0]hexan-3-one
  • 1-Isopropyl-4-methylbicyclo[3.1.0]hexan-3-one
  • NSC 407281

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Literature & References

4-methyl-1-propan-2-ylbicyclo[3.1.0]hexan-3-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):11027
Pubchem (sid):135049026
Pherobase:View
Publications by PubMed
Chemical Composition of the Essential Oils of Three Endemic Species of Anthemis Sect. Hiorthia (DC.) R.Fern. Growing Wild in Sicily and Chemotaxonomic Volatile Markers of the Genus Anthemis L.: An Update.
Anthelmintic activity of crude extract and essential oil of Tanacetum vulgare (Asteraceae) against adult worms of Schistosoma mansoni.
TLC-direct bioautography for determination of antibacterial activity of Artemisia adamsii essential oil.
Central α- and β-thujone: similar anxiogenic-like effects and differential modulation on GABAA receptors in neonatal chicks.
Chemical characterization by GC-MS and in vitro activity against Candida albicans of volatile fractions prepared from Artemisia dracunculus, Artemisia abrotanum, Artemisia absinthium and Artemisia vulgaris.
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.
Chemotype diversity of indigenous Dalmatian sage (Salvia officinalis L.) populations in Montenegro.
Differences in shoot and root terpenoid profiles and plant responses to fertilisation in Tanacetum vulgare.
Study on Gas Chromatography-Mass Spectrometry Fingerprint of Acanthopanax brachypus.
Chemopreventive and antioxidant activity of the chamazulene-rich essential oil obtained from Artemisia arborescens L. growing on the Isle of La Maddalena, Sardinia, Italy.
Comparison of different extraction methods for the determination of α- and β-thujone in sage (Salvia officinalis L.) herbal tea.
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.
Identification of 1,8-cineole, borneol, camphor, and thujone as anti-inflammatory compounds in a Salvia officinalis L. infusion using human gingival fibroblasts.
Identification of genes in Thuja plicata foliar terpenoid defenses.
Attempts to separate (-)-α-thujone, (+)-β-thujone epimers from camphor enantiomers by enantioselective HPLC with polarimetric detection.
Monoterpene α-thujone exerts a differential inhibitory action on GABA(A) receptors implicated in phasic and tonic GABAergic inhibition.
Antibacterial, allelopathic and antioxidant activities of essential oil of Salvia officinalis L. growing wild in the Atlas Mountains of Morocco.
Thujone and thujone-containing herbal medicinal and botanical products: toxicological assessment.
Essential oil variation in the populations of Artemisia spicigera from northwest of Iran: chemical composition and antibacterial activity.
Essential oils and their compositions as spatial repellents for pestiferous social wasps.
Chemical composition and antimicrobial activity of essential oils from Scabiosa arenaria Forssk: growing wild in Tunisia.
Modulation of GABAergic synaptic currents and current responses by α-thujone and dihydroumbellulone.
Chemical composition and antifungal activity of Artemisia nilagirica essential oil growing in northern hilly areas of India.
Composition of the essential oil of Origanum tyttanthum from Tajikistan.
Seasonal influence on gene expression of monoterpene synthases in Salvia officinalis (Lamiaceae).
Toxicology and carcinogenesis studies of alpha,beta-thujone (CAS No. 76231-76-0) in F344/N rats and B6C3F1 mice (gavage studies).
Distribution and chemical polymorphism of the essential oils of Achillea cartilaginea growing wild in Lithuania.
Thujone inhibits lung metastasis induced by B16F-10 melanoma cells in C57BL/6 mice.
Augmentation of humoral and cell mediated immune responses by Thujone.
Determination of the biologically active flavour substances thujone and camphor in foods and medicines containing sage (Salvia officinalis L.).
Thujone corrects cholesterol and triglyceride profiles in diabetic rat model.
Modulation of genotoxicity and DNA repair by plant monoterpenes camphor, eucalyptol and thujone in Escherichia coli and mammalian cells.
Skeletal muscle fatty acid oxidation is not directly associated with AMPK or ACC2 phosphorylation.
Morphological characterisation and agronomical parameters of different species of Salvia sp. (Lamiaceae).
Oil constituents of Artemisia nilagirica var. septentrionalis growing at different altitudes.
Chemical composition and antibacterial potential of Artemisia arborescens L. essential oil.
Metabolism of α-thujone in human hepatic preparations in vitro.
Composition and intraspecific chemical variability of the essential oil from Artemisia herba-alba growing wild in a Tunisian arid zone.
Influence of ionic interactions on essential oil and phenolic diterpene composition of Dalmatian sage (Salvia officinalis L.).
Insecticidal activity and chemical composition of the essential oils of Artemisia lavandulaefolia and Artemisia sieversiana from China.
Risk assessment of thujone in foods and medicines containing sage and wormwood--evidence for a need of regulatory changes?
Chemical composition of the essential oil of Salvia officinalis L. from Romania.
Thujone, a component of medicinal herbs, rescues palmitate-induced insulin resistance in skeletal muscle.
Antimicrobial activity and essential oil composition of a new T. argyrophyllum (C. Koch) Tvzel var. argyrophyllum chemotype.
Essential oil composition of Achillea clusiana from Bulgaria.
Influence of gibberellin and daminozide on the expression of terpene synthases and on monoterpenes in common sage (Salvia officinalis).
Artemisia fukudo essential oil attenuates LPS-induced inflammation by suppressing NF-kappaB and MAPK activation in RAW 264.7 macrophages.
Antibacterial and antioxidant activities of the essential oil of Artemisia echegarayi Hieron. (Asteraceae).
Chemosystematic value of the essential oil composition of Thuja species cultivated in Poland-antimicrobial activity.
Variations in essential oil, phenolic compounds, and antioxidant activity of tunisian cultivated Salvia officinalis L.
Absinthe, epileptic seizures and Valentin Magnan.
Compositional variation of the essential oils of Artemisia afra Jacq. from three provinces in South Africa--a case study of its safety.
Motile cilia of human airway epithelia are chemosensory.
Essential oil composition of Tanacetum vulgare subsp. siculum (Guss.) Raimondo et Spadaro (Asteraceae) from Sicily.
Essential oil composition of Artemisia herba-alba from southern Tunisia.
Cytotoxicity, antimicrobial activity and composition of essential oil from Tanacetum balsamita L. subsp. balsamita.
Long-term stability of thujone, fenchone, and pinocamphone in vintage preban absinthe.
Chemical composition of the essential oil of Achillea umbellata growing in Greece.
Cooperative effects on radical recombination in CYP3A4-catalyzed oxidation of the radical clock beta-thujone.
Chemical composition of the essential oil of Artemisia absinthium growing wild in Iran.
Tunisian Salvia officinalis L. and Schinus molle L. essential oils: their chemical compositions and their preservative effects against Salmonella inoculated in minced beef meat.
[Thujone-attributable effects of absinthe are only an urban legend--toxicology uncovers alcohol as real cause of absinthism].
Chemical composition of vintage preban absinthe with special reference to thujone, fenchone, pinocamphone, methanol, copper, and antimony concentrations.
Tick repellent substances in the essential oil of Tanacetum vulgare.
[Thujone].
Absinthe and tobacco--a new look at an old problem? (Comment on: Absinthe--is its history relevant for current public health?).
Insecticidal properties of essential oils from Lippia turbinata and Lippia polystachya (Verbenaceae) against Culex quinquefasciatus (Diptera: Culicidae).
[Chemical diversity of the biological active ingredients of salvia officinalis and some closely related species].
[Absinthe - history of dependence to thujone or to alcohol?].
Composition of the essential oil of Salvia officinalis L. from various European countries.
Chemical composition and antifungal activity of the essential oils of three species of Artemisia on some soil-borne phytopathogens.
The essential oil of Solvia cabulica.
Biotransformation of terpenoids by mammals, microorganisms, and plant-cultured cells.
Phytochemical analysis of the essential oil of Achillea millefolium L. from various European Countries.
Absinthe--a review.
Antimutagenic effect of essential oil of sage (Salvia officinalis L.) and its monoterpenes against UV-induced mutations in Escherichia coli and Saccharomyces cerevisiae.
Absinthe, the nervous system and painting.
Radical intermediates in the catalytic oxidation of hydrocarbons by bacterial and human cytochrome P450 enzymes.
Vapor phase toxicity of marjoram oil compounds and their related monoterpenoids to Blattella germanica (Orthoptera: Blattellidae).
Antiviral activities of extracts and selected pure constituents of Ocimum basilicum.
Thujone--cause of absinthism?
Absinthe: attention performance and mood under the influence of thujone.
Biosynthesis of the irregular monoterpene artemisia ketone, the sesquiterpene germacrene D and other isoprenoids in Tanacetum vulgare L. (Asteraceae).
Alpha- and beta-thujone radical rearrangements and isomerizations. A new radical clock.
Radical rebound mechanism in cytochrome P-450-catalyzed hydroxylation of the multifaceted radical clocks alpha- and beta-thujone.
The human taste receptor hTAS2R14 responds to a variety of different bitter compounds.
Chemotypical variation of tansy (Tanacetum vulgare L.) from 40 different locations in Norway.
Alpha-thujone reduces 5-HT3 receptor activity by an effect on the agonist-reduced desensitization.
GC analysis of essential oils in the rumen fluid after incubation of Thuja orientalis twigs in the Rusitec system.
Plant odour processing in the antennal lobe of male and female grapevine moths, Lobesia botrana (Lepidoptera: Tortricidae).
Volatile metabolites from Salvia fruticosa as antifungal agents in soilborne pathogens.
Essential oils produced by in vitro shoots of sage (Salvia officinalis L.).
Composition and antimicrobial activity of the essential oil of Artemisia absinthium from Croatia and France.
[Studies of volatile oils from the flowers of Chrysanthemum nankingense and Chrysanthemum indicum].
Monoterpene effect on feeding choice by deer.
Absinthe: enjoying a new popularity among young people?
Composition and antimicrobial activity of the essential oil of Achillea multifida.
Absinthe: return of the Green Fairy.
Seasonal changes in the composition of the essential oil extract of East Mediterranean sage (Salvia libanotica) and its toxicity in mice.
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.
Towards the industrial production of medicinal tincture by ultrasound assisted extraction.
alpha- and beta-Thujones (herbal medicines and food additives): synthesis and analysis of hydroxy and dehydro metabolites.
Acaricidal properties of Artemisia absinthium and Tanacetum vulgare (Asteraceae) essential oils obtained by three methods of extraction.
Absinthe and gamma-aminobutyric acid receptors.
Alpha-thujone (the active component of absinthe): gamma-aminobutyric acid type A receptor modulation and metabolic detoxification.
Absinthe: what's your poison? Though absinthe is intriguing, it is alcohol in general we should worry about.
Essential oils from dalmatian sage (Salvia officinalis l.): variations among individuals, plant parts, seasons, and sites.
Thujone exhibits low affinity for cannabinoid receptors but fails to evoke cannabimimetic responses.
Absinthe--return of the green fairy.
Comparison of conventional and ultrasonically assisted extractions of pharmaceutically active compounds from Salvia officinalis.
Porphyrogenic properties of the terpenes camphor, pinene, and thujone (with a note on historic implications for absinthe and the illness of Vincent van Gogh).
Floral volatiles ofTanacetum vulgare L. attractive toLobesia botrana den. et schiff. females.
Volatile Constituents of Achillea grandifolia.
Another diagnosis for Vincent Van Gogh?
Terpenoid biotransformation in mammals. V. Metabolism of (+)-citronellal, (+-)-7-hydroxycitronellal, citral, (-)-perillaldehyde, (-)-myrtenal, cuminaldehyde, thujone, and (+-)-carvone in rabbits.
Absinthe.
Vincent van Gogh and the thujone connection.
Metabolism of monoterpenes: specificity of the dehydrogenases responsible for the biosynthesis of camphor, 3-thujone, and 3-isothujone.
A study on tansy chemotypes.
Isolation and identification of mosquito repellents inArtemisia vulgaris.
Quantitative analysis of alpha, beta-thujone, pulegone, safrole, coumarin and beta-asarone in alcoholic beverages by selected-ion monitoring.
Constituents of the Essential Oil of Artemisia coerulescens.
[Condensation of thujone with biogenic amines and amino acids].
Absinthe: behind the emerald mask.
Van Gogh's vision: thujone intoxication.

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
HMDB (The Human Metabolome Database):HMDB41631
FooDB:FDB021854
Export Tariff Code:2914.29.5000
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 152.23672485352
Specific gravity @ 25 °C
Pounds per Gallon
Boiling Point 200 to 201°C @ 760 mm Hg
Boiling Point 113 to 114°C @ 50 mm Hg
Vapor Pressure 0.323 mmHg @ 25 °C
Flash Point TCC Value 64.44 °C TCC
logP (o/w) 2.044 est
Solubility
alcohol Yes
water, 407.7 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Thujonic
cedar, thujonic, spicy, woody
General comment At 10.00 % in dipropylene glycol. cedarleaf

Occurrences

Potential Uses

Applications
Odor purposes Cedar , Tansy oil replacer , Wormwood oil replacer
Flavoring purposes Tansy oil replacer

Safety Information

Safety information

Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
IFRA Critical Effect:
Neurotoxicity
View the IFRA Standard
View IFRA Standards Library for complete information.
Please review Amendment 49 IFRA documentation for complete information.
IFRA RESTRICTION LIMITS IN THE FINISHED PRODUCT (%):
Category 1: Products applied to the lips
0.11 %
Category 2: Products applied to the axillae
0.21 %
Category 3: Products applied to the face/body using fingertips
0.32 %
Category 4: Products related to fine fragrance
1.40 %
Category 5: Products applied to the face and body using the hands (palms), primarily leave-on
Category 5A: Body lotion products applied to the body using the hands (palms), primarily leave-on
0.095 %
Category 5B: Face moisturizer products applied to the face using the hands (palms), primarily leave-on
0.032 %
Category 5C: Hand cream products applied to the hands using the hands (palms), primarily leave-on
0.016 %
Category 5D: Baby Creams, baby Oils and baby talc
0.0053 %
Category 6: Products with oral and lip exposure
0.095 %
Category 7: Products applied to the hair with some hand contact
Category 7A: Rinse-off products applied to the hair with some hand contact
0.24 %
Category 7B: Leave-on products applied to the hair with some hand contact
0.24 %
Category 8: Products with significant anogenital exposure
0.0053 %
Category 9: Products with body and hand exposure, primarily rinse off
0.13 %
Category 10: Household care products with mostly hand contact
Category 10A: Household care excluding aerosol products (excluding aerosol/spray products)
0.13 %
Category 10B: Household aerosol/spray products
0.22 %
Category 11: Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate
Category 11A: Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
0.0053 %
Category 11B: Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
0.0053 %
Category 12: Products not intended for direct skin contact, minimal or insignificant transfer to skin
9.50 %
Notes:
IFRA FLAVOR REQUIREMENTS:

Due to the possible ingestion of small amounts of fragrance ingredients from their use in products in Categories 1 and 6, materials must not only comply with IFRA Standards but must also be recognized as safe as a flavoring ingredient as defined by the IOFI Code of Practice (www.iofi.org). For more details see chapter 1 of the Guidance for the use of IFRA Standards.

Recommendation for beta-thujone flavor usage levels up to:
not for flavor use.

Safety references

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):1125-12-8
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :11027
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
4-methyl-1-propan-2-ylbicyclo[3.1.0]hexan-3-one
Chemidplus:0001125128