2,4,6-Trichloroanisole
Chemical primarily responsible for cork taint in wines (TCA) / From Wikipedia, the free encyclopedia
2,4,6-Trichloroanisole (TCA) is a chemical compound that represents one of the strongest of off-flavors, substances "generated naturally in foods/beverages [that considerably] deteriorate the quality" of such products.[1][2] As of 2000, TCA was considered the primary chemical compound responsible for the phenomenon of cork taint in wines,[3][1] and it has an unpleasant earthy, musty and moldy smell.[2]
Names | |
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Preferred IUPAC name
1,3,5-Trichloro-2-methoxybenzene | |
Other names
2,4,6-Trichloroanisole TCA 2,4,6-Trichloromethoxybenzene | |
Identifiers | |
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3D model (JSmol) |
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ChEBI | |
ChemSpider |
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ECHA InfoCard | 100.001.585 |
EC Number |
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KEGG |
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PubChem CID |
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RTECS number |
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UNII | |
CompTox Dashboard (EPA) |
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Properties | |
C7H5Cl3O | |
Molar mass | 211.47 g·mol−1 |
Melting point | 60 to 62 °C (140 to 144 °F; 333 to 335 K) |
Boiling point | 140 °C (284 °F; 413 K) at 28 Torr |
Hazards | |
GHS labelling: | |
Warning | |
H302, H319, H413 | |
P264, P270, P273, P280, P301+P312, P305+P351+P338, P330, P337+P313, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Chemically, TCA is a chlorinated derivative of anisole, and it is a formed by the biomethylation of 2,4,6-trichlorophenol.[4][5] More generally, it may be produced when naturally occurring airborne fungi and bacteria are presented with chlorinated phenolic compounds, which they then convert into chlorinated anisole derivatives.[6] Species implicated include those of the genera Aspergillus, Penicillium, Actinomycetes, Botrytis (e.g. Botrytis cinerea), Rhizobium, or Streptomyces.[7][8][6]
The chlorophenol precursor, 2,4,6-trichlorophenol, is used as a fungicide; more generally, related compounds can originate as contaminants found in some pesticides and wood preservatives, or as by-products of the chlorine bleaching process used to sterilize or bleach wood, paper, and other materials.[9]
TCA has also been suggested as cause of the "Rio defect" in coffees from Brazil and other parts of the world,[10] which refers to a taste described as "medicinal, phenolic, or iodine-like".[5] In investigation of the mechanism of its role in producing off-flavor effects, it was found to "attenuate olfactory transduction by suppressing cyclic nucleotide-gated channels, without evoking odorant responses."[1]