2,4,6-Trichloroanisole

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2,4,6-Trichloroanisole
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2,4,6-Trichloroanisole (TCA) is an organic compound with the formula Template:Chem2. 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.[1][2] It is also a component of some drinking waters.[3] It has also been detected in blood samples.[4]

Wine

As of 2000, TCA was considered the primary chemical compound responsible for the phenomenon of cork taint in wines,[5][1] and it has an unpleasant earthy, musty and moldy smell.[2]

Coffee

TCA has also been suggested as cause of the "Rio defect" in coffees from Brazil and other parts of the world,[6] which refers to a taste described as "medicinal, phenolic, or iodine-like".[7] 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]

Formation

TCA is formed by the methylation of 2,4,6-trichlorophenol.[8][7] 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.[9] Species implicated include those of the genera Aspergillus, Penicillium, Actinomycetes, Botrytis (e.g. Botrytis cinerea), Rhizobium, or Streptomyces.[10][11][9]

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.[12]

Further reading

  • Script error: No such module "citation/CS1".
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  • Script error: No such module "Citation/CS1". An early primary research report on the role of TCA in cork taint.

See also

References

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  1. ↑ a b c Script error: No such module "Citation/CS1".Template:Primary source inline
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  6. ↑ These include Central and South America.Script error: No such module "Unsubst".
  7. ↑ a b Script error: No such module "Citation/CS1". Note, at best, this source states that 2,4,6-trichlorophenol is "the probable precursor of TCA".
  8. ↑ Script error: No such module "citation/CS1".
  9. ↑ a b Script error: No such module "Citation/CS1".
  10. ↑ Script error: No such module "citation/CS1".
  11. ↑ With regard to circumstantial evidence, Spodone, et al., op. cit., note that Rio off-flavor is associated with "beans heavily infested with various fungi (Aspergilli, Fusaria, Penicillia, Rhizopus, etc.) and bacteria (Lactobacilli, Streptrococci)".
  12. ↑ NTP (National Toxicology Program). 2021. "2,4,6-Trichlorophenol", Report on Carcinogens, Fifteenth Edition. Research Triangle Park, NC: U.S. Department of Health and Human Services, Public Health Service. https://ntp.niehs.nih.gov/go/roc15 DOI: https://doi.org/10.22427/NTP-OTHER-1003

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