2,4,6-Trichloroanisole (TCA) is an organic compound with the formula . It is one of several isomers of trichloroanisole. It is a colorless solid.
Occurrence
2,4,6-Trichloroanisole represents one of the strongest of off-flavors, substances "generated naturally in foods/beverages [that considerably] deteriorate the quality" of such products. It is also a component of some drinking waters. It has also been detected in blood samples.
Wine
As of 2000, TCA was considered the primary chemical compound responsible for the phenomenon of cork taint in wines, which refers to a taste described as "medicinal, phenolic, or iodine-like". 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. Species implicated include those of the genera Aspergillus, Penicillium, Actinomycetes, Botrytis (e.g. Botrytis cinerea), Rhizobium, or Streptomyces.
Further reading
- An early primary research report on the role of TCA in cork taint.
See also
- 2,4,6-Tribromoanisole