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alpha-thujone

Chemical Structure

General Material Information

Preferred name alpha-thujone
Trivial Name Thujone
Short Description bicyclo[3.1.0]hexan-3-one, 4-methyl-1- (1-methylethyl)-, [1S-(1a,4a,5a)]-
Formula C10 H16 O
CAS Number 546-80-5
ECHA Number 208-912-2
FDA UNII R0SQ9G0DU5
Nikkaji Number J6.432G
Beilstein Number 4660369
MDL MFCD00135597
xLogP3-AA 2.30 (est)
Bio Activity Summary External link
NMR Predictor External link
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
  • 3-Thujanone, (1S,4R,5R)-(-)-
  • Bicyclo[3.1.0]hexan-3-one, 4-methyl-1-(1-methylethyl)-, [1S-(1α,4α,5α)]-
  • (1S,4R,5R)-4-Methyl-1-(1-methylethyl)bicyclo[3.1.0]hexan-3-one
  • α-Thujone
  • Thujone
  • (-)-Thujone
  • Thujon
  • (-)-α-Thujone
  • NSC 93742
  • Absinthol
  • (1S,4R,5R)-1-Isopropyl-4-methylbicyclo[3.1.0]hexan-3-one

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Literature & References

(1S,4R,5R)-4-methyl-1-propan-2-ylbicyclo[3.1.0]hexan-3-one
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:546-80-5
Pubchem (cid):261491
Pubchem (sid):134977422
Pherobase:View
Publications by PubMed
Chemical composition and antimicrobial activity of essential oils from Acantholippia deserticola, Artemisia proceriformis, Achillea micrantha and Libanotis buchtormensis against phytopathogenic bacteria and fungi.
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.
Determination of volatile organic compounds in the dried leaves of Salvia species by solid-phase microextraction coupled to gas chromatography mass spectrometry.
Artemisia herba-alba essential oil from Buseirah (south Jordan): Chemical characterization and assessment of safe antifungal and anti-inflammatory doses.
Repellent Effect and Metabolite Volatile Profile of the Essential Oil of Achillea millefolium Against Aegorhinus nodipennis (Hope) (Coleoptera: Curculionidae).
Ethnobotanical survey of medicinal plants used in the Maseru district of Lesotho.
Artemisia arborescens "Powis Castle" extracts and α-thujone prevent fruit infestation by codling moth neonates.
Thuja occidentalis L. and its active compound, α-thujone: Promising effects in the treatment of polycystic ovary syndrome without inducing osteoporosis.
The antifungal activity of Artemisia sieberi essential oil from different localities of Iran against dermatophyte fungi.
Inhibitory Effects of Chrysanthemum boreale Essential Oil on Biofilm Formation and Virulence Factor Expression of Streptococcus mutans.
Fumigant toxicity of basil oil compounds and related compounds to Thrips palmi and Orius strigicollis.
Volatile compounds from Achillea tenorii (Grande) growing in the Majella National Park (Italy).
Volatile-oils composition, and bioactivity of the essential oils of Plectranthus barbatus, P. neochilus, and P. ornatus grown in Portugal.
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 composition and general toxicity of essential oils extracted from the aerial parts of Artemisia armeniaca Lam. and A. incana (L.) Druce growing in Iran.
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.
Phytochemical composition of the essential oil of different populations of Stachys lavandulifolia Vahl.
Constituents of Artemisia gmelinii Weber ex Stechm. from Uttarakhand Himalaya: A Source of Artemisia Ketone.
Bioactivities of volatile components from Nepalese Artemisia species.
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.
Chemical composition and anticancer activity of essential oils of Mediterranean sage (Salvia officinalis L.) grown in different environmental conditions.
Terpenoids of plant origin inhibit morphogenesis, adhesion, and biofilm formation by Candida albicans.
Essential oil variation in the populations of Artemisia spicigera from northwest of Iran: chemical composition and antibacterial activity.
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.
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.
Antimicrobial and antioxidant properties of the essential oil of Salvia lanigera from Cyprus.
Chemical composition of the essential oil of Salvia officinalis L. from Romania.
Effects of foliar fertilization and arbuscular mycorrhizal colonization on Salvia officinalis L. growth, antioxidant capacity, and essential oil composition.
Composition at different development stages of the essential oil of four Achillea species grown in Iran.
Essential oil composition of Achillea clusiana from Bulgaria.
Misidentification of tansy, Tanacetum macrophyllum, as yarrow, Achillea grandifolia: a health risk or benefit?
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.
Chemical composition of hydrodistilled essential oil of Artemisia incana (L.) Druce and antimicrobial activity against foodborne microorganisms.
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.
In vitro evaluation of the permeation through reconstructed human epidermis of essentials oils from cosmetic formulations.
Essential oil composition of Tanacetum vulgare subsp. siculum (Guss.) Raimondo et Spadaro (Asteraceae) from Sicily.
Flowerhead volatile oil composition of soilless culture-grown Chrysanthemum balsamita L.
Cytotoxicity, antimicrobial activity and composition of essential oil from Tanacetum balsamita L. subsp. balsamita.
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.
Tunisian Salvia officinalis L. and Schinus molle L. essential oils: their chemical compositions and their preservative effects against Salmonella inoculated in minced beef meat.
Mass propagation and essential oil analysis of Artemisia vulgaris.
Tick repellent substances in the essential oil of Tanacetum vulgare.
Chemical composition and antibacterial activity of essential oil from Artemisia feddei.
Insecticidal properties of essential oils from Lippia turbinata and Lippia polystachya (Verbenaceae) against Culex quinquefasciatus (Diptera: Culicidae).
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.
Comparison of three lychee cultivar odor profiles using gas chromatography-olfactometry and gas chromatography-sulfur detection.
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.
Acaricidal activities of paeonol and benzoic acid from Paeonia suffruticosa root bark and monoterpenoids against Tyrophagus putrescentiae (Acari: Acaridae).
Radical intermediates in the catalytic oxidation of hydrocarbons by bacterial and human cytochrome P450 enzymes.
Chemical composition and antioxidant, antimicrobial, and antifungal activities of the essential oil of Achillea ligustica all.
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.
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.
Antimicrobial activity of Artemisia douglasiana leaf essential oil.
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.
Volatile metabolites from Salvia fruticosa as antifungal agents in soilborne pathogens.
Antibacterial activity and chemical composition of essential oil of Chrysanthemum boreale.
Composition and antimicrobial activity of the essential oil of Achillea multifida.
Organ- and season-dependent variation in the essential oil composition of Salvia officinalis L. cultivated at two different sites.
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.
Production of yarrow (Achillea millefolium L.) in Norway: essential oil content and quality.
Role of human GABA(A) receptor beta3 subunit in insecticide toxicity.
alpha- and beta-Thujones (herbal medicines and food additives): synthesis and analysis of hydroxy and dehydro metabolites.
Volatile chemicals identified in extracts from leaves of Japanese mugwort (Artemisia princeps pamp.).
Composition of essential oil of costmary [Balsamita major (L.) Desf. ] at different growth phases.
Alpha-thujone (the active component of absinthe): gamma-aminobutyric acid type A receptor modulation and metabolic detoxification.
Dynamics of yield components and essential oil production in a commercial hybrid sage (Salvia officinalis x Salvia fruticosa cv. Newe Ya'ar no. 4).
Floral volatiles ofTanacetum vulgare L. attractive toLobesia botrana den. et schiff. females.
Olfactory responses of a specialist and a generalist grasshopper to volatiles ofArtemisia ludoviciana nutt. (Asteraceae).
Constituents of the Essential Oil of Artemisia coerulescens.

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
CHEMBL:View
KEGG (GenomeNet):C09906
HMDB (The Human Metabolome Database):HMDB36115
FooDB:FDB014962
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 @ 20 °C
Pounds per Gallon
Boiling Point 200 to 201°C @ 760 mm Hg
Vapor Pressure 0.323 mmHg @ 25 °C
Flash Point TCC Value 63.89 °C TCC
logP (o/w) 2.044 est
Shelf life 12 months (or longer if stored properly.)
Storage notes Refrigerate in tightly sealed containers.
Solubility
alcohol Yes
water, 407.7 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

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

Occurrences

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xn - Harmful.
R 22 - Harmful if swallowed.
R 36/37/38 - Irritating to eyes, respiratory system, and skin.
S 02 - Keep out of the reach of children.
S 20/21 - When using do not eat, drink or smoke.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36/37/39 - Wear suitable clothing, gloves and eye/face protection.
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:
oral-rat LD50 500 mg/kg
French Demande Patent Document. Vol. #2448856

intravenous-rabbit LD50 0.031 mg/kg
French Demande Patent Document. Vol. #2448856

intravenous-rabbit LD50 31 ug/kg
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 29, Pg. 2, 1940.

intraperitoneal-rat LDLo 120 mg/kg
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Journal of Pharmacology and Experimental Therapeutics. Vol. 65, Pg. 275, 1939.

Dermal Toxicity:
subcutaneous-rabbit LD50 362 mg/kg
Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 29, Pg. 2, 1940.

subcutaneous-mouse LD50 2157 ug/kg
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 29, Pg. 2, 1940.

subcutaneous-rabbit LD50 362 ug/kg
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 29, Pg. 2, 1940.

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
0.032 %
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 alpha-thujone flavor usage levels up to:
not for flavor use.

Safety references

EPI System: View
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):546-80-5
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :261491
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(1S,4R,5R)-4-methyl-1-propan-2-ylbicyclo[3.1.0]hexan-3-one
Chemidplus:0000546805
RTECS:XO9625000 for cas# 546-80-5