Buy Thujone Cas 76231-76-0

Thujone (/ˈθuːdʒoʊn/ ^ⓘ^[2]) is a ketone and a monoterpene that occurs predominantly in two diastereomeric (epimeric) forms: (−)-α-thujone and (+)-β-thujone.^[3]^[4]

Though it is best known as a chemical compound in the spirit absinthe, it is only present in trace amounts and is unlikely to be responsible for the spirit’s purported stimulant and psychoactive effects.^[5]^[6]^[7]

Thujone acts on the GABA_A receptor as an antagonist. As a competitive antagonist of GABA_A receptor, thujone alone is considered to be convulsant,^[8] though by interfering with the inhibitory transmitter GABA, it may convey stimulating, mood-elevating effects at low doses.^{[citation needed]} It is also found in perfumery as a component of several essential oils.

Buy Thujone Cas 76231-76-0

In addition to the naturally occurring (−)-α-thujone and (+)-β-thujone, two other forms are possible: (+)-α-thujone and (−)-β-thujone. In 2016, they were found in nature as well,^[9] in Salvia officinalis.

Buy Thujone Cas 76231-76-0

CAS No.: 76231-76-0

Chemical Name:: ALPHA+BETA-THUJONE

Synonyms: α,β-Thujone;β-thujone, 2-10%;α-thujone, 90-98%;α,β-Thujone;α,β-Thujone (>90%);α,β-Thujone (Standard);THUJONE, (alpha, beta)-;THUJONE, (alpha, beta)-(SG);(1S,5R)-1-Isopropyl-4-methylbicyclo[3.1.0]hexan-3-one;Bicyclo[3.1.0]hexan-3-one, 4-methyl-1-(1-methylethyl)-, (1S,5R)-

CBNumber:: CB7972560

Molecular Formula:: C10H16O

Molecular Weight:: 152.23

MDL Number:: MFCD00135597

MOL File:: 76231-76-0.mol

MSDS File:: SDS

TDS File:: TDS

Last updated:2026-05-28 03:25:34

Product description	Number	Pack Size	Price
α,β-Thujone phyproof? Reference Substance	PHL82669	100MG	$287
Thujone Standard Mixture analytical standard	04314	1ML	$94.2
α,β-Thujone technical, ~70% α-thujone basis, ~10% β-thujone basis	89230	10ml	$133
Thujone Standard Mixture analytical standard	04314	5ML	$371
α,β-Thujone technical, ~70% α-thujone basis, ~10% β-thujone basis	89230	50ml	$402
More product size

Request For Quotation

ALPHA+BETA-THUJONE Properties

Boiling point	84-86 °C/17 mmHg (lit.)
Density	0.925 g/mL at 25 °C (lit.)
refractive index	n20/D 1.455(lit.)
Flash point	64 °C
storage temp.	2-8°C
solubility	Chloroform (Slightly), Dichloromethane (Slightly), DMSO (Slightly)
form	Oil
color	Colourless
Henry’s Law Constant	6.2×10^-1 mol/(m³Pa) at 25℃, HSDB (2015)
InChI	1S/2C10H16O/c21-6(2)10-4-8(10)7(3)9(11)5-10/h26-8H,4-5H2,1-3H3/t7-,8+,10-;7-,8-,10+/m01/s1
InChIKey	AKPBIVZAUPVDMO-APEKEWONSA-N
SMILES	CC(C)[C@@]12C[C@@H]1[C@@H](C)C(=O)C2.CC(C)[C@@]34C[C@@H]3[C@H](C)C(=O)C4
Toxicology and Carcinogenesis	Toxicology and Carcinogenesis Studies of alpha,beta-Thujone (CASRN 76231-76-0) in F344/N Rats and B6C3F1 Mice (Gavage Studies)
FDA UNII	86HK1QRJ4K
UNSPSC Code	85151701
NACRES	NA.24

Buy Thujone Cas 76231-76-0

SAFETY

Risk and Safety Statements

Symbol(GHS)	GHS07
Signal word	Warning
Hazard statements	H302
Precautionary statements	P264-P270-P301+P312-P501
PPE	Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Codes	T
Risk Statements	23/24/25-36/37/38-42/43
Safety Statements	23-26-36/37/39-45
RIDADR	UN 2810 6.1/PG 3
WGK Germany	3
Storage Class	6.1C – Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects
Hazard Classifications	Acute Tox. 4 Oral
Hazardous Substances Data	76231-76-0(Hazardous Substances Data)

ALPHA+BETA-THUJONE price More Price(18)

Manufacturer	Product number	Product description	CAS number	Packaging	Price	Updated	Buy
Sigma-Aldrich	PHL82669	α,β-Thujone phyproof? Reference Substance	76231-76-0	100MG	$287	2026-04-30	Buy
Sigma-Aldrich	04314	Thujone Standard Mixture analytical standard	76231-76-0	1ML	$94.2	2026-04-30	Buy
Sigma-Aldrich	89230	α,β-Thujone technical, ~70% α-thujone basis, ~10% β-thujone basis	76231-76-0	10ml	$133	2026-04-30	Buy
Sigma-Aldrich	04314	Thujone Standard Mixture analytical standard	76231-76-0	5ML	$371	2026-04-30	Buy
Sigma-Aldrich	89230	α,β-Thujone technical, ~70% α-thujone basis, ~10% β-thujone basis	76231-76-0	50ml	$402	2023-06-20	Buy

ALPHA+BETA-THUJONE Chemical Properties, Uses, Production

Uses

α,β-Thujone is a component of the essential oil of Pistacia vera L. It is also used as as a reactant in organic synthesis.

General Description

This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

ALPHA+BETA-THUJONE Preparation Products And Raw materials

Raw materials

Preparation Products

THUJONE

(−)-α-thujone
(+)-α-thujone
(+)-β-thujone
(−)-β-thujone

Sources

Thujone is found in a number of plants, such as arborvitae (genus Thuja, hence the derivation of the name), Nootka cypress, some junipers, mugwort, oregano, common sage (sage oil contain more than 20% from alpha and beta thujone), tansy, and wormwood, most notably grand wormwood (Artemisia absinthium), usually as a mix of isomers in a 1:2 ratio. It is also found in various species of Mentha (mint).

Biosynthesis

The biosynthesis of thujone is similar to the synthesis of other monoterpenes and begins with the formation of geranyl diphosphate (GPP) from dimethylallyl pyrophosphate (DMAPP) and isopentenyl diphosphate (IPP), catalyzed by the enzyme geranyl diphosphate synthase.^[10] Quantitative ¹³C NMR spectroscopic analysis has demonstrated that the isoprene units used to form thujone in plants are derived from the methylerythritol phosphate pathway (MEP).^[11]

The reactions that generate the thujone skeleton in sabinene from GPP are mediated by the enzyme sabinene synthase which has GPP as its substrate.^[10] GPP (1) first isomerizes to linalyl diphosphate (LPP) (2) and neryl diphosphate (NPP) (3). LPP preferentially forms a delocalized allylic cation-diphosphate (4). The ion-pair intermediate then cyclizes in an electrophilic addition to yield the α-terpinyl tertiary cation (5).^[10]

The conversion of GPP to alpha-terpinyl cation.

The α-terpinyl cation (5) then undergoes a 1,2 hydride shift via a Wagner–Meerwein rearrangement, leading to the formation of the terpinen-4-yl cation (6). This cation undergoes a second cyclization to form the thujyl cation intermediate (7) before loss of a proton to form the thujone precursor, (+)-sabinene (8).

The conversion of alpha-terpinyl cation to (+)-sabinene

From (+)-sabinene (8), the proposed biosynthetic route to generate thujone follows a three-step pathway: (+)-sabinene is first oxidized to an isomer of (+)-sabinol (9-1, 9-2) by a cytochrome P450 enzyme, followed by conversion to (+)-sabinone (10) via a dehydrogenase. Finally, a reductase mediates the conversion to α-thujone (11-1) and β-thujone (11-2).^[12] The isomerism of the (+)-sabinol intermediate varies among thujone-producing plants; for instance, in the western redcedar (Thuja plicata), thujone is derived exclusively from the (+)-trans-sabinol intermediate (9-1) whereas in the common garden sage (Salvia officinalis), thujone is formed from the (+)-cis-sabinol intermediate (9-2).

alpha,beta-Thujone

Catalog No.

S637511

CAS No.

76231-76-0

M.F

C10H16O

M. Wt

152.23 g/mol

Availability

In Stock

* This item is exclusively intended for research purposes and is not designed for human therapeutic applications or veterinary use.

Content Navigation

General Information

Crude wormwood oil and pure isomer sourcing cause inconsistent synthesis and excessive costs. This alpha,beta-thujone mixture (CAS 76231-76-0) offers a reproducible, cost-effective solution. • Standardized isomer ratio (~70-98% α, 2-10% β) ensures reliable stereoselective synthesis of sesquiterpenes, avoiding expensive pure isomer isolation. • Essential analytical reference for GC-FID/GC-MS total thujone quantification in absinthe and botanicals, supporting FDA/EU compliance (35 mg/L). • Reflects natural exposure for GABA_A receptor studies, providing translatable toxicological data. Bulk quantities available for industrial R&D.

CAS Number

76231-76-0

Product Name

alpha,beta-Thujone

IUPAC Name

(1S,5R)-4-methyl-1-propan-2-ylbicyclo[3.1.0]hexan-3-one

Molecular Formula

C10H16O

Molecular Weight

152.23 g/mol

InChI

InChI=1S/C10H16O/c1-6(2)10-4-8(10)7(3)9(11)5-10/h6-8H,4-5H2,1-3H3/t7?,8-,10+/m1/s1

InChI Key

USMNOWBWPHYOEA-VWHDNNRLSA-N

SMILES

CC1C2CC2(CC1=O)C(C)C

solubility

Practically insoluble in water
Soluble in alcohol and many organic solvents

Synonyms

(+)-thujone, (-)-thujone, 3-isothujone, 3-thujanone, alpha, beta-thujone, alpha-thujone, beta-thujone, beta-thujone, (1alpha,4alpha,5alpha)-isomer, beta-thujone, (1S-(1alpha,4alpha,5alpha))-isomer, beta-thujone, 1S-(1alpha,4beta,5alpha)-isomer, cis-thujone, thujone

Canonical SMILES

CC1C2CC2(CC1=O)C(C)C

Isomeric SMILES

CC1[C@H]2C[C@]2(CC1=O)C(C)C

The exact mass of the compound alpha,beta-Thujone is unknown and the complexity rating of the compound is unknown. The solubility of this chemical has been described as in water, 407 mg/l at 25 °c (est)practically insoluble in watersoluble in alcohol and many organic solvents. The United Nations designated GHS hazard class pictogram is Acute Toxic;Irritant;Health Hazard, and the GHS signal word is DangerThe storage condition is unknown. Please store according to label instructions upon receipt of goods.Use and application categories indicated by third-party sources: Flavouring Agent -> FLAVOURING_AGENT; -> JECFA Functional Classes. However, this does not mean our product can be used or applied in the same or a similar way.

Purity

≥96% (sum of isomers)

Package Size

1 g, 5 g, 1 ml, 25 ml

alpha,beta-Thujone Procurement and Chemical Overview

alpha,beta-Thujone (CAS 76231-76-0) is a commercially available bicyclic monoterpene ketone mixture, typically comprising ~70–98% (-)-alpha-thujone and ~2–10% (+)-beta-thujone, depending on the technical or analytical grade [1]. Unlike highly purified single isomers, this specific mixture serves as the primary industrial and laboratory standard due to its natural abundance in botanical extracts such as Artemisia absinthium and Thuja occidentalis. For procurement professionals and synthetic chemists, the alpha,beta-thujone mixture provides a highly cost-effective, scalable chiral synthon that retains the critical C-1 and C-5 stereocenters of the bicyclo[3.1.0]hexane scaffold required for the total synthesis of complex sesquiterpenes [2]. Additionally, it functions as the definitive analytical reference material for regulatory compliance testing in the food, beverage, and fragrance sectors, where total thujone quantification is legally mandated [1].

Procurement Fit

Reference StandardDefined α:β ratio (α 90–98%) for reproducible GC/HPLC calibration and regulatory compliance testing

Research ToolIsomer-defined material for GABAA receptor modulation and diastereomer-specific neurotoxicology studies

References

alpha,beta-Thujone Substitution Risks

Substituting the standardized alpha,beta-thujone mixture (CAS 76231-76-0) with either crude wormwood essential oil or pure single isomers introduces severe process and cost inefficiencies. Crude botanical extracts contain highly variable concentrations of thujone alongside interfering compounds like absinthin, rendering them entirely unsuitable for precise stereoselective synthesis or quantitative analytical calibration [1]. Conversely, attempting to procure pure (-)-alpha-thujone (CAS 546-80-5) or (+)-beta-thujone (CAS 471-15-8) is commercially prohibitive for large-scale synthesis; the boiling point difference between the two epimers is less than 1°C (approx. 201°C vs. 201.8°C), making fractional distillation exceptionally difficult and expensive [1]. Furthermore, for regulatory and toxicological testing, pure alpha-thujone fails to accurately model human exposure, as it overestimates GABA_A receptor antagonism toxicity compared to the natural isomer ratio found in the standard mixture [2].

Substitution Risk

Generic thujone mixtures

Undefined α:β ratios introduce up to 5-fold uncertainty in neurotoxicity endpoints and receptor pharmacology outcomes

Natural essential oils

Wide batch-to-batch isomer variability (α 13–49% in sage oil) prevents reproducible quantification and dose-response modeling

Regulatory compliance gap

EU and US thujone limits require accurate sum-of-isomers measurement; uncharacterized materials compromise audit-ready method validation

References

Quantitative Evidence for alpha,beta-Thujone Selection

Chiral Synthon Cost and Scalability

For the total synthesis of complex sesquiterpenes such as (+)-alpha-eudesmol and (-)-alpha-selinene, the alpha,beta-thujone mixture provides the necessary bicyclo[3.1.0]hexane scaffold without the prohibitive costs associated with pure isomer isolation[2]. Because the epimers differ only at the C-4 methyl group—which is often manipulated or rendered irrelevant during downstream ring-opening—the conserved C-1 and C-5 stereocenters in the mixture are synthetically identical to those in pure (-)-alpha-thujone [2]. The sub-1°C boiling point differential (201°C vs. 201.8°C) makes separating the isomers via fractional distillation commercially unviable [1].

Evidence Dimension	Boiling point differential and separation feasibility
Target Compound Data	alpha,beta-Thujone mixture (CAS 76231-76-0) used directly as a scalable chiral synthon
Comparator Or Baseline	Pure (-)-alpha-thujone (CAS 546-80-5) and (+)-beta-thujone (CAS 471-15-8)
Quantified Difference	<1°C boiling point difference makes pure isomer isolation prohibitively expensive compared to the technical mixture
Conditions	Large-scale stereoselective organic synthesis

Procuring the mixture avoids the prohibitive cost of pure isomers while providing the exact same stereochemical utility for complex terpenoid synthesis.

Acute Neurotoxicity

Head-to-head

α-Thujone LD5087.5 mg/kg s.c.

β-Thujone LD50442.2 mg/kg s.c.

Supports isomer-specific neurotoxicity screening

Mice, subcutaneous; 5-fold difference

Simultaneous Isomer Calibration for Regulatory Testing

Regulatory frameworks, such as the EU limit of 35 mg/L in absinthe, mandate the quantification of total thujone, which is the sum of alpha and beta epimers. Utilizing the alpha,beta-thujone standard (CAS 76231-76-0) allows for the simultaneous GC-MS retention mapping and calibration of both isomers in a single run, achieving limits of detection (LOD) of approximately 0.11 µg/mL for alpha-thujone and 0.10 µg/mL for beta-thujone [1]. A pure alpha-thujone standard cannot establish the retention time or calibration curve for the beta epimer, necessitating the purchase of a second, highly expensive pure standard [1].

Evidence Dimension	Chromatographic retention mapping and calibration efficiency
Target Compound Data	alpha,beta-Thujone standard maps both epimers simultaneously (LOD ~0.11 µg/mL and ~0.10 µg/mL)
Comparator Or Baseline	Pure (-)-alpha-thujone standard
Quantified Difference	The mixture halves the reference material acquisition cost and reduces GC-MS calibration runs by 50% for total thujone quantification
Conditions	GC-MS analysis of botanical extracts and beverages

Procurement of the mixed standard streamlines regulatory compliance workflows and significantly reduces analytical consumable costs for food safety laboratories.

GABAA Receptor Modulation

Head-to-head

α-Thujone (78 nmol)Reversed stress-induced receptor recruitment

β-Thujone (78 nmol)No reversal observed

Highlights diastereomer-specific receptor modulation

Neonatal chick model, i.c.v.

Toxicological Profiling and Baseline Accuracy

The National Toxicology Program (NTP) specifically utilizes the alpha,beta-thujone mixture (CAS 76231-76-0) for in vivo gavage studies because it accurately reflects the natural exposure ratio, typically 7:1 to 10:1 alpha to beta, found in botanical products [2]. Pure (-)-alpha-thujone is approximately 2 to 3 times more potent as a GABA_A receptor competitive antagonist than the beta epimer, with a significantly lower LD50 of approximately 45 mg/kg in mice[1]. Testing pure alpha-thujone artificially inflates the perceived neurotoxicity of natural extracts, whereas the mixture provides a translatable baseline for establishing allowable daily intake limits [2].

Evidence Dimension	In vivo toxicological relevance and LD50 accuracy
Target Compound Data	alpha,beta-Thujone mixture accurately models natural botanical exposure ratios
Comparator Or Baseline	Pure (-)-alpha-thujone
Quantified Difference	Pure alpha-thujone overestimates toxicity by 2-3x due to higher GABA_A antagonism potency (LD50 ~45 mg/kg) compared to the beta epimer
Conditions	In vivo pharmacological and toxicological assays assessing neurotoxicity

Ensures that toxicological assays yield data that is directly translatable to regulatory risk assessments, avoiding artificial toxicity inflation.

GABAA Channel Binding

Reported

Competitive [3H]EBOB inhibitor; inhibits recombinant α1β2γ2s currents vs. menthol enhancement (496±113%)

Supports GABAA antagonist screening context

Xenopus oocytes; picrotoxinin site

CYP Metabolism

Head-to-head

α-Thujone in mice2-hydroxylation pathway present

β-Thujone in mice2-hydroxylation absent

Requires isomer-defined toxicokinetic modeling

Species-specific; CYP3A4 relevance

Standard vs. Natural Extracts

Head-to-head

Analytical Standardα-thujone 90–98%

Natural Sourcesα-thujone 13–49%, variable

Essential for reproducible analytical quantification

GC/HPLC reference; regulatory compliance

Regulatory Limits

Class-level

5–35 mg/kg (EU) / <10 ppm (US)

Supports regulatory compliance testing

Tiered limits by beverage category

alpha,beta-Thujone Industrial and Laboratory Applications

Chiral Synthon for Sesquiterpene Synthesis

Directly downstream of its scalable viability, the alpha,beta-thujone mixture is the preferred starting material for the stereoselective synthesis of complex sesquiterpenes, such as (+)-alpha-eudesmol, (-)-alpha-selinene, and (+)-beta-cyperone. By leveraging the conserved C-1 and C-5 stereocenters of the bicyclo[3.1.0]hexane scaffold, synthetic chemists can bypass the prohibitive costs of pure isomer isolation [1].

Regulatory Compliance Testing for Food and Beverages

Driven by the need for simultaneous isomer calibration, analytical grade alpha,beta-thujone is essential for GC-FID and GC-MS quantification of total thujone in absinthe, sage extracts, and other botanical products. This ensures compliance with FDA and EU maximum residue limits (e.g., 35 mg/L) using a single, cost-effective reference standard [2].

In Vivo Toxicological Modeling

Because it accurately reflects the natural isomeric ratio found in plant extracts, the alpha,beta-thujone mixture is the standard compound for pharmacological assays evaluating GABA_A receptor antagonism and neurotoxicity. It is the mandated form for studies aiming to establish translatable allowable daily intake (ADI) limits for herbal medicines and flavorings [3].

Application Fit Matrix

Analytical method validation for thujone

Defined α:β compositional range

Calibration linearity and LOD

GABAA receptor pharmacology screening

Noncompetitive antagonist profile

Negative control response vs. menthol

Isomer-specific toxicokinetic studies

Isomer-defined metabolic pathway

CYP3A4 metabolite profiling

Diastereomer-specific neurotoxicity research

Defined diastereomer ratio for dose-response

LD50 reproducibility across batches

References

Specification

Physical Description

Solid

Color/Form

Colorless or almost colorless liquid

XLogP3

2.3

Hydrogen Bond Acceptor Count

Exact Mass

152.120115130 g/mol

Monoisotopic Mass

152.120115130 g/mol

Boiling Point

203 °C

Heavy Atom Count

Density

Specific gravity: 0.915-0.919 at 20 °C/20 °C

LogP

log Kow = 2.65 (est)

Decomposition

Hazardous decomposition products formed under fire conditions. – Carbon oxides. /Alpha-Thujone/

Others

Melting Point

< 25 °C

UNII

R0SQ9G0DU5
86HK1QRJ4K

GHS Hazard Statements

Aggregated GHS information provided by 40 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;
H301 (95%): Toxic if swallowed [Danger Acute toxicity, oral];
H311 (95%): Toxic in contact with skin [Danger Acute toxicity, dermal];
H315 (95%): Causes skin irritation [Warning Skin corrosion/irritation];
H317 (95%): May cause an allergic skin reaction [Warning Sensitization, Skin];
H319 (95%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];
H331 (95%): Toxic if inhaled [Danger Acute toxicity, inhalation];
H334 (95%): May cause allergy or asthma symptoms or breathing difficulties if inhaled [Danger Sensitization, respiratory];
H335 (95%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure;
Respiratory tract irritation];
Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Therapeutic Uses

EXPL THER … The aim of this investigation was to study the cytotoxicity of Salvia officinalis L. (sage) essential oil. Salvia officinalis essential oil was gained by aqueous extraction from plant material and subsequently analyzed by gas chromatography. The cytotoxicity of the essential oil on the squamous human cell carcinoma cell line of the oral cavity (UMSCC1) was assessed with the XTT assay. These experiments revealed the half maximal inhibitory concentration (IC(50)) of the essential oil. It was used in the microarray-based analysis of gene expression of UMSSC1 cells. The results were submitted to a signaling pathway analysis. The main constituents of Salvia officinalis essential oil include the monoterpenes thujone, beta-pinene, and 1,8-cineol. Low concentrations of the essential oil increased vitality of the UMSCC1 cells. Beyond the concentration of the IC(50) of 135 ug/mL, sage essential oil reduced UMSSC1 cells viability to a minimum. In the microarray gene expression analysis, genes involved in cancer, cellular growth and proliferation, cell death, cell morphology, cell cycle, gene expression, and DNA repair were the most prominent. The three most significantly regulated pathways by sage were aryl hydrocarbon receptor signaling, cell cycle (G1/S checkpoint) regulation, and p53 signaling. To the best of our knowledge, this study suggests for the first time the ability of Salvia officinalis essential oil to inhibit human HNSCC cell growth. The therapeutic potential of sage essential oil might exceed that of its common use in otorhinolaryngology. /Salvia officinalis essential oil/
EXPL THER In the present study, the chemical constituents of Artemisia fukudo essential oil (AFE) were investigated using GC-MS. The major constituents were alpha-thujone (48.28%), beta-thujone (12.69%), camphor (6.95%) and caryophyllene (6.01%). /Investigators/ also examined the effects of AFE on the production of nitric oxide (NO), prostaglandin E(2) (PGE(2)), tumour necrosis factor (TNF)-alpha, interleukin (IL)-1beta, and IL-6, in lipopolysaccharide (LPS)-activated RAW 264.7 macrophages. Western blotting and RT-PCR tests indicated that AFE has potent dose-dependent inhibitory effects on pro-inflammatory cytokines and mediators. /the authors/ investigated the mechanism by which AFE inhibits NO and PGE(2) by examining the level of nuclear factor-kappaB (NF-kappaB) activation within the mitogen-activated protein kinase (MAPK) pathway, which is an inflammation-induced signal pathway in RAW 264.7 cells. AFE inhibited LPS-induced ERK, JNK, and p38 phosphorylation. Furthermore, AFE inhibited the LPS-induced phosphorylation and degradation of Ikappa-B-alpha, which is required for the nuclear translocations of the p50 and p65 NF-kappaB subunits in RAW 264.7 cells. /These/ results suggest that AFE might exert an anti-inflammatory effect by inhibiting the expression of pro-inflammatory cytokines. Such an effect is mediated by a blocking of NF-kappaB activation which consequently inhibits the generation of inflammatory mediators in RAW264.7 cells. AFE may be useful for treating inflammatory diseases.
EXPL THER The antimetastatic potential of thujone, a naturally occurring monoterpene, was evaluated. Metastasis was induced in C57BL/6 mice by injecting highly metastatic B16F-10 melanoma cells through the lateral tail vein. Administration of thujone (1 mg/kg body weight), prophylactically and simultaneously with tumor induction, inhibited tumor nodule formation in the lungs by 59.45% and 57.54%, respectively, with an increase in the survival rate (33.67% and 32.16%) of the metastatic tumor bearing animals. These results correlated with biochemical parameters such as lung collagen hydroxyproline, hexosamine and uronic acid contents, serum sialic acid and gamma-glutamyl transpeptidase levels, and histopathological analysis. Treatment with thujone downregulated the production of proinflammatory cytokines such as tumor necrosis factor-alpha, interleukin (IL)-1beta, IL-6, and granulocyte-monocyte colony-stimulating factor. Thujone administration downregulated the expression of matrix metalloproteinase (MMP)-2, MMP-9, extracellular signal-regulated kinase (ERK)-1, ERK-2, and vascular endothelial growth factor (VEGF) and also upregulated the expression of nm-23, tissue inhibitor of metalloproteinase (TIMP)-1, and TIMP-2 in the lung tissue of metastasis-induced animals. Treatment with thujone inhibited the activity of MMP-2 and MMP-9 in gelatin zymographic analysis. Thujone treatment significantly inhibited the invasion of B16F-10 melanoma cells across the collagen matrix in a Boyden chamber. Thujone also inhibited the adhesion of tumor cells to collagen-coated microtire plate wells and the migration of B16F-10 melanoma cells across a polycarbonate filter in vitro. These results indicate that Thujone can inhibit the lung metastasis of B16F-10 cells through inhibition of tumor cell proliferation, adhesion, and invasion, as well as by regulating expression of MMPs, VEGF, ERK-1, ERK-2, TIMPs, nm23, and levels of proinflammatory cytokines and IL-2 in metastatic animals.
EXPL THER Thujone is thought to be the main constituent of medicinal herbs that have antidiabetic properties. Therefore, we examined whether thujone ameliorated palmitate-induced insulin resistance in skeletal muscle. Soleus muscles were incubated for < or = 12 hr without or with palmitate (2 mM). Thujone (0.01 mg/mL), in the presence of palmitate, was provided in the last 6 hr of incubation. Palmitate oxidation, AMPK/acetyl-CoA carboxylase (ACC) phosphorylation and insulin-stimulated glucose transport, plasmalemmal GLUT4, and AS160 phosphorylation were examined at 0, 6, and 12 hr. Palmitate treatment for 12 hr reduced fatty acid oxidation (-47%), and insulin-stimulated glucose transport (-71%), GLUT4 translocation (-40%), and AS160 phosphorylation (-26%), but it increased AMPK (+51%) and ACC phosphorylations (+44%). Thujone (6-12 hr) fully rescued palmitate oxidation and insulin-stimulated glucose transport, but only partially restored GLUT4 translocation and AS160 phosphorylation, raising the possibility that an increased GLUT4 intrinsic activity may also have contributed to the restoration of glucose transport. Thujone also further increased AMPK phosphorylation but had no further effect on ACC phosphorylation. Inhibition of AMPK phosphorylation with adenine 9-beta-d-arabinofuranoside (Ara) (2.5 mM) or compound C (50 muM) inhibited the thujone-induced improvement in insulin-stimulated glucose transport, GLUT4 translocation, and AS160 phosphorylation. In contrast, the thujone-induced improvement in palmitate oxidation was only slightly inhibited (< or = 20%) by Ara or compound C. Thus, while thujone, a medicinal herb component, rescues palmitate-induced insulin resistance in muscle, the improvement in fatty acid oxidation cannot account for this thujone-mediated effect. Instead, the rescue of palmitate-induced insulin resistance appears to occur via an AMPK-dependent mechanism involving partial restoration of insulin-stimulated GLUT4 translocation.
For more Therapeutic Uses (Complete) data for alpha, beta-Thujone (11 total), please visit the HSDB record page.

Mechanism of Action

The gamma-aminobutyric acid type A (GABA(A)) receptor is the target for the major insecticides alpha-endosulfan, lindane, and fipronil and for many analogs. Their action as chloride channel blockers is directly measured by binding studies with [(3)H]ethynylbicycloorthobenzoate ([(3)H]EBOB). This study tests the hypothesis that GABA(A) receptor subunit composition determines the sensitivity and selectivity of insecticide toxicity. Human receptor subtypes were expressed individually (alpha1, alpha6, beta1, beta3, and gamma2) and in combination in insect Sf9 cells. Binding parameters were similar for [(3)H]EBOB in the beta3 homooligomer, alpha1beta3gamma2 heterooligomer, and native brain membranes, but toxicological profiles were very different. Surprisingly, alpha-endosulfan, lindane, and fipronil were all remarkably potent on the recombinant beta3 homooligomeric receptor (IC50 values of 0.5-2.4 nM), whereas they were similar in potency on the alpha1beta3gamma2 subtype (IC50 values of 16-33 nM) and highly selective on the native receptor (IC50 values of 7.3, 306, and 2470 nM, respectively). The selectivity order for 29 insecticides and convulsants as IC50 ratios for native/beta3 or alpha1beta3gamma2/beta3 was as follows: fipronil > lindane > 19 other insecticides including alpha-endosulfan and picrotoxinin > 4 trioxabicyclooctanes and dithianes (almost nonselective) > tetramethylenedisulfotetramine, 4-chlorophenylsilatrane, or alpha-thujone. Specificity between mammals and insects at the target site (fipronil > lindane > alpha-endosulfan) paralleled that for toxicity. Potency at the native receptor is more predictive for inhibition of GABA-stimulated chloride uptake than that at the beta3 or alpha1beta3gamma2 receptors. Therefore, the beta3 subunit contains the insecticide target and other subunits differentially modulate the binding to confer compound-dependent specificity and selective toxicity.
alpha-Thujone, a constituent of wormwood, has been suspected to cause adverse psychoactive reactions in addicted drinkers of absinthe. While the content of alpha-thujone in absinthe is too low for such effects, at higher doses it can indeed induce seizures and inhibit GABA(A) receptors (GABA(A)Rs). The effect of alpha-thujone on GABAergic synaptic currents and the mechanisms by which it modulates GABA(A)Rs remain unknown. To address these issues, cultured hippocampal neurons were used to investigate the action of alpha-Thujone on GABAergic miniature inhibitory postsynaptic currents (mIPSCs) and on responses to exogenous GABA applications. Since lipophi

alpha,beta-Thujone (CAS 76231-76-0) | Pharma …

Buy alpha,beta-Thujone (CAS 76231-76-0) from SMolecule. Scalable chiral synthon & reference standard …
Thujone Standard Mixture analytical standard 76231-76-0

Find documentation for the products that you have recently purchased in the Document Library.
a,b-Thujone technical, a-thujone 70 , b-thujone 10 76231-76-0

Description Application α,β-Thujone can be used as a chiral synthon in the total synthesis of (+)-β-cyperone and several bicyclo [3. …

Thujone | CAS No. 76231-76-0 | Clearsynth

Buy Thujone CAS No- 76231-76-0, a high quality product from Clearsynth, a Leading Manufacturer and Exporter of Thujone …
ALPHA+BETA-THUJONE | 76231-76-0 – ChemicalBook
May 28, 2026 · ALPHA+BETA-THUJONE (CAS 76231-76-0) information, including chemical properties, structure, melting point, …
- Boiling point: 84-86 °C/17 mmHg (lit.)
- Flash point: 64 °C
- Density: 0.925 g/mL at 25 °C (lit.)
- refractive index: n20/D 1.455 (lit.)
CAS 76231-76-0 Thujone Standard Mixture – Analytical Products / Alfa …

Thujone Standard Mixture (76231-76-0) Quality Assurance, In Stock. 24h Delivery. Free Inquiry.

Buy Online CAS Number 76231-76-0 – TRC – Alpha,Beta-Thujone …

Purchase online CAS Number 76231-76-0 – TRC – Alpha,Beta-Thujone (>90%). High Quality CRMs, Reference Materials, Proficiency …
CAS No : 76231-76-0 | Product Name : α,β-Thujone

Buy highly pure α,β-Thujone, CAS No : 76231-76-0, Mol.Formula : C10H16O, Mol.Weight : 152.2, from Pharmaffiliates. Login as …

CAS 76231-76-0 (α,β-Thujone) – BOC Sciences

α,β-Thujone (CAS# 76231-76-0) is a component of the essential oil of Pistacia vera L. It is also used as as a reactant in organic …

Thujone Standard Mixture, MilliporeSigma Supelco – Buffers and …

Reviews

There are no reviews yet.

Be the first to review “Buy Thujone Cas 76231-76-0”