2,4,6-trichloroanisole
benzene, 1,3,5-trichloro-2-methoxy- (9CI)
Identification
| Name | 2,4,6-trichloroanisole |
| CAS Number | 87-40-1 |
| EINECS | 201-743-5 |
| FDA UNII | 31O3X41254 |
| Molecular Formula | C7 H5 Cl3 O |
| Molecular Weight | 211.47205000 |
| MDL Number | MFCD00000588 |
| Nikkaji Number | J4.277C |
| Beilstein | 2329219 |
| XlogP3 | 4.00 (est) |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 61.50 °C. @ 760.00 mm Hg |
| Boiling Point | 241.00 °C. @ 760.00 mm Hg |
| Vapor Pressure | 0.023000 mmHg @ 20.00 °C. |
| Flash Point | 213.00 °F. TCC ( 100.40 °C. ) (est) |
| logP (o/w) | 4.110 |
| Soluble in | water, 10 mg/L @ 20 °C (exp) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| 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 | natural substances and extractives |
| Recommendation for 2,4,6-trichloroanisole usage levels up to | not for fragrance use. |
| Recommendation for 2,4,6-trichloroanisole flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
anisole, 2,4,6-trichloro- (8CI)
benzene, 1,3,5-trichloro-2-methoxy-
benzene, 1,3,5-trichloro-2-methoxy- (9CI)
methyl 2,4,6-trichlorophenyl ether
2,4,6-
trichloranisole
2,4,6-
trichloro-1-methoxybenzene
1,3,5-
trichloro-2-methoxybenzene
tyrene
PubMed:
A rapid space-resolved solid-phase microextraction method as a powerful tool to determine contaminants in wine based on their volatility.
PubMed:
The Problem of 2,4,6-Trichloroanisole in Cork Planks Studied by Attenuated Total Reflection Infrared Spectroscopy: Proof of Concept.
PubMed:
A simple and sensitive vortex assisted liquid-liquid microextraction method for the simultaneous determination of haloanisoles and halophenols in wines.
PubMed:
Using corona discharge-ion mobility spectrometry for detection of 2,4,6-Trichloroanisole.
PubMed:
Extraction-less, rapid assay for the direct detection of 2,4,6-trichloroanisole (TCA) in cork samples.
PubMed:
Simultaneous determination of ten taste and odor compounds in drinking water by solid-phase microextraction combined with gas chromatography-mass spectrometry.
PubMed:
Gas chromatography-mass spectrometry determination of earthy-musty odorous compounds in waters by two phase hollow-fiber liquid-phase microextraction using polyvinylidene fluoride fibers.
PubMed:
Occurrence of earthy and musty odor compounds (geosmin, 2-methylisoborneol and 2,4,6-trichloroanisole) in biologically treated wastewater.
PubMed:
Cyclic voltammetry: a tool to quantify 2,4,6-trichloroanisole in aqueous samples from cork planks boiling industrial process.
PubMed:
2,4,6-trichloroanisole is a potent suppressor of olfactory signal transduction.
PubMed:
Different headspace solid phase microextraction--gas chromatography/mass spectrometry approaches to haloanisoles analysis in wine.
PubMed:
Experimental design for the optimization of the derivatization reaction in determining chlorophenols and chloroanisoles by headspace-solid-phase microextraction-gas chromatography/mass spectrometry.
PubMed:
Analysis of corky off-flavour compounds at ultra trace level with multidimensional gas chromatography-electron capture detection.
PubMed:
Ionic liquids as novel stationary phases in gas liquid chromatography: inverse or normal isotope effect?
PubMed:
[Determination of two mouldy compounds in cork by gas chromatography-mass spectrometry].
PubMed:
Headspace-multicapillary column-ion mobility spectrometry for the direct analysis of 2,4,6-trichloroanisole in wine and cork samples.
PubMed:
[Determination of 2,4,6-trichloroanisole in wine by head-space solid phase micro-extraction and gas chromatography-mass spectrometry].
PubMed:
Headspace-single drop microextraction with a commercial capillary electrophoresis instrument.
PubMed:
Method development and validation for the determination of 2,4,6-tribromoanisole, 2,4,6-tribromophenol, 2,4,6-trichloroanisole, and 2,4,6-trichlorophenol in various drug products using stir bar sorptive extraction and gas chromatography-tandem mass spectrometry detection.
PubMed:
A framework for identifying characteristic odor compounds in municipal wastewater effluent.
PubMed:
Accurate analysis of trace earthy-musty odorants in water by headspace solid phase microextraction gas chromatography-mass spectrometry.
PubMed:
Optimisation of a sensitive method based on ultrasound-assisted emulsification-microextraction for the simultaneous determination of haloanisoles and volatile phenols in wine.
PubMed:
The potential of ion mobility spectrometry (IMS) for detection of 2,4,6-trichloroanisole (2,4,6-TCA) in wine.
PubMed:
Concentrations of organochlorine pesticides and 2,4,6-trichloroanisole in cork bark.
PubMed:
Destruction of chloroanisoles by using a hydrogen peroxide activated method and its application to remove chloroanisoles from cork stoppers.
PubMed:
Trace level analysis of corky off-flavor compounds: development of a new analytical method based on solid phase extraction and analysis by multidimensional gas chromatography with mass spectrometric detection.
PubMed:
Odorous compounds in municipal wastewater effluent and potable water reuse systems.
PubMed:
Direct determination of 2,4,6-tricholoroanisole in wines by single-drop ionic liquid microextraction coupled with multicapillary column separation and ion mobility spectrometry detection.
PubMed:
Multivariate analysis of volatile compounds detected by headspace solid-phase microextraction/gas chromatography: A tool for sensory classification of cork stoppers.
PubMed:
Volatile compounds in samples of cork and also produced by selected fungi.
PubMed:
Development of a cellular biosensor for the detection of 2,4,6-trichloroanisole (TCA).
PubMed:
Selectable one-dimensional or two-dimensional gas chromatography-olfactometry/mass spectrometry with preparative fraction collection for analysis of ultra-trace amounts of odor compounds.
PubMed:
Origin and incidence of 2-methoxy-3,5-dimethylpyrazine, a compound with a "fungal" and "corky" aroma found in cork stoppers and oak chips in contact with wines.
PubMed:
Concentrations of viable airborne fungal spores and trichloroanisole in wine cellars.
PubMed:
Identification of a new source of contamination of Quercus sp. oak wood by 2,4,6-trichloroanisole and its impact on the contamination of barrel-aged wines.
PubMed:
Sensitive determination of 2,4,6-trichloroanisole in water samples by ultrasound assisted emulsification microextraction prior to gas chromatography-tandem mass spectrometry analysis.
PubMed:
Ultrasound-assisted emulsification microextraction for determination of 2,4,6-trichloroanisole in wine samples by gas chromatography tandem mass spectrometry.
PubMed:
Development of a microwave assisted extraction method for the analysis of 2,4,6-trichloroanisole in cork stoppers by SIDA-SBSE-GC-MS.
PubMed:
Sensory screening for large-format natural corks by "dry soak" testing and its correlation to headspace solid-phase microextraction (SPME) gas chromatography/mass spectrometry (GC/MS) releasable trichloroanisole (TCA) analysis.
PubMed:
Off-odor compounds produced in cork by isolated bacteria and fungi: a gas chromatography-mass spectrometry and gas chromatography-olfactometry study.
PubMed:
Modeling quality of premium spanish red wines from gas chromatography-olfactometry data.
PubMed:
Catalytic ozonation for degradation of 2, 4, 6-trichloroanisole in drinking water in the presence of gamma-AlOOH.
PubMed:
Ozonation catalyzed by the raw bauxite for the degradation of 2,4,6-trichloroanisole in drinking water.
PubMed:
Multi-residue off-flavour profiling in wine using stir bar sorptive extraction-thermal desorption-gas chromatography-mass spectrometry.
PubMed:
Molecular fingerprinting by PCR-denaturing gradient gel electrophoresis reveals differences in the levels of microbial diversity for musty-earthy tainted corks.
PubMed:
Comparison of two SPME fibers for the extraction of some off-flavor cork-taint compounds in bottled wines investigated by GC-HRMS.
PubMed:
Copper UPD as non-specific adsorption barrier in electrochemical displacement immunosensors.
PubMed:
Analysis of earthy and musty odors in water samples by solid-phase microextraction coupled with gas chromatography/ion trap mass spectrometry.
PubMed:
Application of robust NiTi-ZrO2-PEG SPME fiber in the determination of haloanisoles in cork stopper samples.
PubMed:
Biodegradation of 2,4,6-TCA by the white-rot fungus Phlebia radiata is initiated by a phase I (O-demethylation)-phase II (O-conjugation) reactions system: implications for the chlorine cycle.
PubMed:
Comparison of stir bar sorptive extraction and solid-phase microextraction to determine halophenols and haloanisoles by gas chromatography-ion trap tandem mass spectrometry.
PubMed:
Determination of 2,4,6-trichloroanisole and 2,4,6-tribromoanisole in wine using microextraction in packed syringe and gas chromatography-mass spectrometry.
PubMed:
Transformation ability of fungi isolated from cork and grape to produce 2,4,6-trichloroanisole from 2,4,6-trichlorophenol.
PubMed:
Environmental significance of O-demethylation of chloroanisoles by soil bacterial isolates as a mechanism that improves the overall biodegradation of chlorophenols.
PubMed:
Multiple headspace solid-phase microextraction for eliminating matrix effect in the simultaneous determination of haloanisoles and volatile phenols in wines.
PubMed:
Assessment of the matrix effect on the headspace solid-phase microextraction (HS-SPME) analysis of chlorophenols in wines.
PubMed:
Application of fractional factorial experimental and Box-Behnken designs for optimization of single-drop microextraction of 2,4,6-trichloroanisole and 2,4,6-tribromoanisole from wine samples.
PubMed:
Analysis for chloroanisoles and chlorophenols in cork by stir bar sorptive extraction and gas chromatography-mass spectrometry.
PubMed:
Optimisation of a microwave-assisted extraction method for the simultaneous determination of haloanisoles and halophenols in cork stoppers.
PubMed:
Analysis of off-flavor compounds in water at sub part per trillion level by GC/MS with programmable temperature vaporizer inlet.
PubMed:
Optimisation of a headspace solid-phase microextraction with on-fiber derivatisation method for the direct determination of haloanisoles and halophenols in wine.
PubMed:
Rapid headspace solid-phase microextraction/gas chromatographic/mass spectrometric assay for the quantitative determination of some of the main odorants causing off-flavours in wine.
PubMed:
Fungal strains isolated from cork stoppers and the formation of 2,4,6-trichloroanisole involved in the cork taint of wine.
PubMed:
Fast and sensitive method to determine chloroanisoles in cork using an internally cooled solid-phase microextraction fiber.
PubMed:
Determination of haloanisols in white wine by immunosorbent solid-phase extraction followed by enzyme-linked immunosorbent assay.
PubMed:
Comparative study of two chromatographic methods for quantifying 2,4,6-trichloranisole in wines.
PubMed:
Automated trace determination of earthy-musty odorous compounds in water samples by on-line purge-and-trap-gas chromatography-mass spectrometry.
PubMed:
Multiple response optimisation based on desirability functions of a microwave-assisted extraction method for the simultaneous determination of chloroanisoles and chlorophenols in oak barrel sawdust.
PubMed:
Assays on the simultaneous determination and elimination of chloroanisoles and chlorophenols from contaminated cork samples.
PubMed:
Non-destructive method to determine halophenols and haloanisoles in cork stoppers by headspace sorptive extraction.
PubMed:
Determination of 2,4,6-trichloroanisole and 2,4,6-tribromoanisole on ng L-1 to pgL-1 levels in wine by solid-phase microextraction and gas chromatography-high-resolution mass spectrometry.
PubMed:
Routine analysis of off-flavor compounds in water at sub-part-per-trillion level by large-volume injection GC/MS with programmable temperature vaporizing inlet.
PubMed:
Ethanol/Water extraction combined with solid-phase extraction and solid-phase microextraction concentration for the determination of chlorophenols in cork stoppers.
PubMed:
Use of multiple headspace solid-phase microextraction and pervaporation for the determination of off-flavours in wine.
PubMed:
Quantification of chloroanisoles in cork using headspace solid-phase microextraction and gas chromatography with electron capture detection.
PubMed:
Simultaneous picogram determination of "earthy-musty" odorous compounds in water using solid-phase microextraction and gas chromatography-mass spectrometry coupled with initial cool programmable temperature vaporizer inlet.
PubMed:
Determination of 2,4,6-trichloroanisole and guaiacol in cork stoppers by pressurised fluid extraction and gas chromatography-mass spectrometry.
PubMed:
Identification of 2,4,6-trichloroanisole (TCA) causing a musty/muddy off-flavor in sake and its production in rice koji and moromi mash.
PubMed:
Migration of contaminants by gas phase transfer from carton board and corrugated board box secondary packaging into foods.
PubMed:
Highly selective solid-phase extraction and large volume injection for the robust gas chromatography-mass spectrometric analysis of TCA and TBA in wines.
PubMed:
Detection of 2,4,6-trichloroanisole in chlorinated water at nanogram per litre levels by SPME-GC-ECD.
PubMed:
Determination of odour-causing volatile organic compounds in cork stoppers by multiple headspace solid-phase microextraction.
PubMed:
Removal of earthy-musty odorants in drinking water by powdered activated carbon.
PubMed:
Determination of odorous mixed chloro-bromoanisoles in water by solid-phase micro-extraction and gas chromatography-mass detection.
PubMed:
Purge-and-trap preconcentration system coupled to capillary gas chromatography with atomic emission detection for 2,4,6-trichloroanisole determination in cork stoppers and wines.
PubMed:
Dynamic headspace coupled to perevaporation for the analysis of anisoles in wine by gas chromatography-ion-trap tandem mass spectrometry.
PubMed:
Optimisation of a headspace solid-phase microextraction method for the direct determination of chloroanisoles related to cork taint in red wine.
PubMed:
Determination of chloroanisole compounds in red wine by headspace solid-phase microextraction and gas chromatography-mass spectrometry.
PubMed:
Analysis of anisoles in wines using pervaporation coupled to gas chromatography-mass spectrometry.
PubMed:
Isolation and identification of 2-methoxy-3,5-dimethylpyrazine, a potent musty compound from wine corks.
PubMed:
Formation and emission of chloroanisoles as indoor pollutants.
PubMed:
Optimization of stir bar sorptive extraction applied to the determination of odorous compounds in drinking water.
PubMed:
Stir bar sorptive extraction for the analysis of wine cork taint.
PubMed:
Immunochemical determination of 2,4,6-trichloroanisole as the responsible agent for the musty odor in foods. 2. Immunoassay evaluation.
PubMed:
Immunochemical determination of 2,4,6-trichloroanisole as the responsible agent for the musty odor in foods. 1. Molecular modeling studies for antibody production.
PubMed:
Accurate determination of 2,4,6-trichloroanisole in wines at low parts per trillion by solid-phase microextraction followed by GC-ECD.
PubMed:
Fast screening method for determining 2,4,6-trichloroanisole in wines using a headspace-mass spectrometry (HS-MS) system and multivariate calibration.
PubMed:
Analysis of off-flavors in the aquatic environment by stir bar sorptive extraction-thermal desorption-capillary GC/MS/olfactometry.
PubMed:
Application of stir bar sorptive extraction for wine analysis.
PubMed:
Determination of 2,4,6-trichloroanisole in wines by headspace solid-phase microextraction and gas chromatography-electron-capture detection.
PubMed:
Cork taint of wines: role of the filamentous fungi isolated from cork in the formation of 2,4,6-trichloroanisole by o methylation of 2,4,6-trichlorophenol.
PubMed:
Evaluation of an extraction method in the determination of the 2,4,6-trichloroanisole content of tainted cork.
PubMed:
Application of low-temperature glassy carbon films in solid-phase microextraction.
PubMed:
Determination of trace amounts of off-flavor compounds in drinking water by stir bar sorptive extraction and thermal desorption GC-MS.
PubMed:
The determination of six taste and odour compounds in water using Ambersorb 572 and high resolution mass spectrometry.
PubMed:
Trends of organochlorine compounds in Finnish inland waters. Results of mussel incubation monitoring 1984-1998.
PubMed:
Cork taint in wine: scientific knowledge and public perception: a critical review.
PubMed:
Supercritical fluid extraction of 2,4,6-trichloroanisole from cork stoppers.
PubMed:
Analysis of 2,4,6-trichloroanisole in wines using solid-phase microextraction coupled to gas chromatography-mass spectrometry.
PubMed:
Identification of 2,4,6-trichloroanisole in several essential oils.