2,4,6-Tribromoanisole

2,4,6-Tribromoanisole[1]
IUPAC name

1,3,5-Tribromo-2-methoxybenzene
Other names

Tribromoanisole; TBA
Identifiers
CAS number 607-99-8
PubChem 11839
ChemSpider 11345 Y
UNII DO7M3M4LX5 Y
ChEBI CHEBI:38703 Y
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C7H5Br3O
Molar mass 344.826
Melting point

84-88 °C
Boiling point

297-299 °C
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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.[2]

Tribromoanisole is a fungal metabolite of 2,4,6-tribromophenol, which is used as a fungicide in place of the banned pentachlorophenol. It can be found in minute traces on packaging materials stored in the presence of fiberboard treated with 2,4,6-tribromophenol. Traces of TBA cause mustiness in packaged foods.[3]

Tribromoanisole 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 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[4] (or 3.4-7.9 ng/l[5]) so even very minute amounts can be detected. It causes unpleasant earthy, musty and moldy aromas.

Consumer product recalls

In recent years, 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 Tylenol due to an odor caused by tribromoanisole.[6][7] In this case, 2,4,6-tribromophenol was used to treat wooden pallets on which product packaging materials were transported and stored.[6] In 2010 and in 2011, Pfizer recalled bottles of Lipitor after reports of an odor linked to the packaging bottles.[8] 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.[9]

See also

References

  1. ^ 2,4,6-Tribromoanisole at Sigma-Aldrich
  2. ^ Chatonnet P, Bonnet S, Boutou S, Labadie MD (2004). "Identification and responsibility of 2,4,6-tribromoanisole in musty, corked odors in wine". J Agric Food Chem 52 (5): 1255–1262. doi:10.1021/jf030632f. PMID 14995130. 
  3. ^ Frank B. Whitfield, Jodie L. Hill, and Kevin J. Shaw (1997). "2,4,6-Tribromoanisole: a Potential Cause of Mustiness in Packaged Food". J. Agric. Food Chem. 45 (3): 889–893. doi:10.1021/jf960587u. 
  4. ^ http://www.restek.com/Technical-Resources/Technical-Library/General-Interest/general_A031
  5. ^ http://www.wawgg.org/files/documents/THK_&_Richard_Larsen_Tasting_Room_Training_power_point.pdf
  6. ^ a b Tylenol Recall Expands, WebMD Health News, January 18, 2010
  7. ^ McNeil Consumer Healthcare Announces Voluntary Recall Of One Product Lot Of TYLENOL® Extra Strength Caplets 225 Count Distributed In The U.S.
  8. ^ 38,000 more bottles of Lipitor recalled over odor complaints, CNN.com, October 30, 2010
  9. ^ Lipitor (atorvastatin) 40 mg: Recall Specific Bottles, drugs.com, Dec 23, 2010