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2,4,6-Tribromoanisole

2,4,6-Tribromoanisole (TBA) is a chemical compound that is a brominated derivative of anisole. It is one of the chemicals responsible for cork taint.

Tribromoanisole is a fungal metabolite of 2,4,6-tribromophenol, which is used as a fungicide. It can be found in minute traces on packaging materials stored in the presence of fiberboard treated with 2,4,6-tribromophenol. These traces can cause an unpleasant mustiness in packaged foods.

Tribromoanisole is usually produced when naturally occurring airborne fungi or bacteria (usually Aspergillus sp., Penicillium sp., Actinomycetes, Botrytis cinerea, Rhizobium sp., or Streptomyces) are presented with brominated phenolic compounds, which they then convert into bromoanisole derivatives. The bromophenols can originate from various contaminants including those found in some pesticides and wood preservatives. They can also migrate from other objects such as shipping pallets treated by bromophenols.

Tribromoanisole has a very low odor detection threshold. It is 0.08-0.3 parts per trillion (ppt) in water and 2-6 ppt in wine (or 3.4-7.9 ng/L) so even very minute amounts can be detected. It causes unpleasant earthy, musty and moldy aromas.

Consumer product recalls

There have been several events in which consumer products were recalled due to odors caused by tribromoanisole on product packaging. In 2010 and 2011, Johnson & Johnson voluntarily recalled some over-the-counter products, including Benadryl, Motrin, Rolaids, Simply Sleep, St. Joseph Aspirin, and Tylenol, due to an odor caused by tribromoanisole. In this case, a supplier had used 2,4,6-tribromophenol to treat wooden pallets on which product packaging materials were transported and stored. Pfizer said the bottles were supplied by a third-party manufacturer and determined the cause to be exposure of the bottles to low levels of tribromoanisole as they were shipped or stored.

References

References

  1. "2,4,6-Tribromoanisole".
  2. (2004). "Identification and responsibility of 2,4,6-tribromoanisole in musty, corked odors in wine". J Agric Food Chem.
  3. (1997). "2,4,6-Tribromoanisole: a Potential Cause of Mustiness in Packaged Food". J. Agric. Food Chem..
  4. (2010). "Fast Screening of Recalled Tylenol for Tribromoanisole and Related Adulterants Using QuEChERS and GC-TOFMS".
  5. "WAWGG Annual Meeting 2011: Tasting Room Staff Training".
  6. DeNoon, Daniel J.. (December 29, 2009). "Tylenol Recall Expands".
  7. (June 28, 2011). "McNeil Consumer Healthcare Announces Voluntary Recall Of One Product Lot Of TYLENOL Extra Strength Caplets 225 Count Distributed In The U.S.".
  8. (October 30, 2010). "38,000 more bottles of Lipitor recalled over odor complaints".
  9. (December 23, 2010). "Lipitor (atorvastatin) 40 mg: Recall Specific Bottles".
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