2,4,6-trichloroanisole

2,4,6-Trichloroanisole

Names
Preferred IUPAC name 1,3,5-Trichloro-2-methoxybenzene
Other names 2,4,6-Trichloroanisole TCA 2,4,6-Trichloromethoxybenzene
Identifiers
CAS Number	87-40-1 N
3D model (Jmol)	Interactive image Interactive image
ChEBI	CHEBI:19333 Y
ChemSpider	6620 Y
ECHA InfoCard	100.001.585
KEGG	C11510 Y
RTECS number	MFCD00000588
InChI InChI=1S/C7H5Cl3O/c1-11-7-5(9)2-4(8)3-6(7)10/h2-3H,1H3 Y Key: WCVOGSZTONGSQY-UHFFFAOYSA-N Y InChI=1/C7H5Cl3O/c1-11-7-5(9)2-4(8)3-6(7)10/h2-3H,1H3 Key: WCVOGSZTONGSQY-UHFFFAOYAT
SMILES COc1c(Cl)cc(Cl)cc1Cl Clc1cc(Cl)cc(Cl)c1OC
Properties
Chemical formula	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
R-phrases	R22 R36
S-phrases	S26
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

2,4,6-Trichloroanisole (TCA) is a chemical compound that is a chlorinated derivative of anisole. TCA 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, which refers to a taste described as medicinal, phenolic, or iodine-like.

TCA is usually produced when naturally occurring airborne fungi and 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 synthesized by reaction of hypochlorites with lignin. They can also migrate from other objects such as shipping pallets treated by chlorophenols.

The odor of TCA is not directly perceived. Instead, the molecule distorts the perception of smell by suppressing olfactory signal transduction. The effect occurs at very low concentrations (single parts per trillion), so even very minute amounts of TCA can be detected. It causes unpleasant earthy, musty and moldy aromas.