| 2,4,6-Trichloroanisole | |
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2,4,6-Trichloroanisole |
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Other names
TCA |
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| Identifiers | |
| CAS number | 87-40-1 |
| ChemSpider | 6620 |
| KEGG | C11510 |
| ChEBI | CHEBI:19333 |
| RTECS number | MFCD00000588 |
| Jmol-3D images | Image 1 Image 2 |
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| Properties | |
| Molecular formula | C7H5Cl3O |
| Molar mass | 211.47 g/mol |
| Melting point |
60-62 °C |
| Boiling point |
140 °C at 28 torr |
| Hazards | |
| R-phrases | R22 R36 |
| S-phrases | S26 |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
2,4,6-Trichloroanisole (TCA) is a chemical compound that is a chlorinated derivative of anisole. Trichloroanisole is a fungal metabolite of 2,4,6-trichlorophenol, which is used as a fungicide. It can be found in minute traces on packaging materials stored in the presence of fiberboard treated with trichlorophenol.
TCA is the chemical primarily responsible for cork taint in wines. TCA has also been implicated as a major component of the "Rio defect" in coffees from Central and South America.[1]
Trichloroanisole is usually produced when naturally occurring airborne fungi and/or bacteria (usually Aspergillus sp., Penicillium sp., Actinomycetes, Botrytis cinerea, Rhizobium sp., or Streptomyces) are presented with chlorinated phenolic compounds, which they then convert into chlorinated anisole derivatives. The chlorophenols can originate from various contaminants such as those found in some pesticides and wood preservatives. Chlorophenols can also be a product of the chlorine bleaching process used to sterilize or bleach wood, paper, and other materials; they can be synthetized by reaction of hypochlorites with lignin. They can also migrate from other objects such as shipping pallets treated by chlorophenols.
Trichloroanisole has a very low odor detection threshold (single parts per trillion), so even very minute amounts can be detected. It causes unpleasant earthy, musty and moldy aromas.