2,4,6-trichloroanisole

2,4,6-Trichloroanisole (TCA) is a chemical compound that is a derivative of anisole. TCA is a white, crystalline solid that is slightly soluble in water, but more soluble in organic solvents. It is notable for its strong, musty odor which humans can detect in very low concentrations, as low as a few parts per trillion (ppt).

Chemical Structure and Properties

TCA has the chemical formula C7H5Cl3O. It consists of a benzene ring substituted with three chlorine atoms and one methoxy group. The presence of the chlorine atoms makes the molecule highly electronegative, which contributes to its low solubility in water.

Production and Uses

TCA is not produced commercially on a large scale, but it can be synthesized in the laboratory by the chlorination of anisole in the presence of a Lewis acid catalyst such as aluminium chloride.

In the wine industry, TCA is known for causing cork taint, a condition that spoils the taste and aroma of wine. It is believed to originate from the use of chlorinated compounds as fungicides or cleaning agents, which can react with naturally occurring phenols in the cork to produce TCA.

Health Effects

Exposure to TCA can cause a variety of health effects. Ingestion or inhalation of TCA can cause symptoms such as nausea, vomiting, and headache. Long-term exposure can lead to liver and kidney damage.

Detection and Removal

TCA can be detected in wine through sensory analysis or by using analytical techniques such as gas chromatography-mass spectrometry (GC-MS).

Removal of TCA from wine is challenging due to its low solubility in water and high affinity for organic materials. Several methods have been proposed, including the use of activated carbon or synthetic polymers that can adsorb TCA.

See Also

• Cork taint
• Anisole
• Chloroanisoles