Molecule of the Week

2,4,6-Trichloroanisole

December 23, 2013

2,4,6-Trichloroanisole (TCA), first synthesized by M. Kohn and M. Heller in 1925, was formerly used as an “assistant” in polyester fiber dyeing. It is also a fungal metabolite produced from the fungicide 2,4,6-trichlorophenol.

TCA, however, is mainly known for causing cork taint that can give wine a musty smell and taste. Until recently, the prevailing wisdom was that it was generated by molds in contaminated corks. But H. Takeuchi and T. Kurahashi of Osaka University (Japan) discovered that TCA contaminates many foods and beverages and that it blocks a protein ion channel associated with olfactory sensing. It may also cause foods to spoil, which would intensify their off-taste.

More about this molecule from CAS, the most authoritative and comprehensive source for chemical information.

3D rendering of the Molecule of the Week: 2,4,6-Trichloroanisole