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2,4,6-Trichloroanisole

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2,4,6-Trichloroanisole
Chemical structure of 2,4,6-trichloroanisole
Names
IUPAC name 2,4,6-Trichloroanisole
Other names TCA
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.001.585 Edit this at Wikidata
KEGG
RTECS number
  • MFCD00000588
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C7H5Cl3O/c1-11-7-5(9)2-4(8)3-6(7)10/h2-3H,1H3Key: WCVOGSZTONGSQY-UHFFFAOYSA-N
  • InChI=1/C7H5Cl3O/c1-11-7-5(9)2-4(8)3-6(7)10/h2-3H,1H3Key: WCVOGSZTONGSQY-UHFFFAOYAT
SMILES
  • COc1c(Cl)cc(Cl)cc1Cl
  • Clc1cc(Cl)cc(Cl)c1OC
Properties
Chemical formula C7H5Cl3O
Molar mass 211.47 g/mol
Melting point 60-62 °C
Boiling point 140 °C at 28 torr
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

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.

See also

References

  1. Spadone, Jean Claude (1990). "Analytical investigation of Rio off-flavor in green coffee". Journal of Agricultural and Food Chemistry. 38: 226–233. doi:10.1021/jf00091a050. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
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