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.[2]

2,4,6-Tribromoanisole[1]
Skeletal formula of 2,4,6-tribromoanisole
Ball-and-stick model of the 2,4,6-tribromoanisole molecule
Names
Preferred IUPAC name
1,3,5-Tribromo-2-methoxybenzene
Other names
Tribromoanisole; TBA
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.156.226
UNII
  • InChI=1S/C7H5Br3O/c1-11-7-5(9)2-4(8)3-6(7)10/h2-3H,1H3 ☒N
    Key: YXTRCOAFNXQTKL-UHFFFAOYSA-N ☒N
  • InChI=1/C7H5Br3O/c1-11-7-5(9)2-4(8)3-6(7)10/h2-3H,1H3
  • COC1=C(C=C(C=C1Br)Br)Br
  • COc1c(Br)cc(Br)cc1Br
Properties
C7H5Br3O
Molar mass 344.828 g·mol−1
Melting point 84 to 88 °C (183 to 190 °F; 357 to 361 K)
Boiling point 297 to 299 °C (567 to 570 °F; 570 to 572 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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.[3]

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[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

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, a supplier had used 2,4,6-tribromophenol 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". 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. Whitfield, Frank B.; Hill, Jodie L.; Shaw, Kevin J. (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. Thomas, Jason & Cochran, Jack (2010). "Fast Screening of Recalled Tylenol® for Tribromoanisole and Related Adulterants Using QuEChERS and GC-TOFMS". Restek Corporation. Archived from the original on July 27, 2017. Retrieved June 29, 2011.
  5. Henick-Kling, Thomas & Larsen, Richard. "WAWGG Annual Meeting 2011: Tasting Room Staff Training" (PDF). Washington Association of Wine Grape Growers. Archived from the original (PDF) on September 29, 2011.
  6. DeNoon, Daniel J. (December 29, 2009). "Tylenol Recall Expands". WebMD Health News.
  7. "McNeil Consumer Healthcare Announces Voluntary Recall Of One Product Lot Of TYLENOL® Extra Strength Caplets 225 Count Distributed In The U.S." Food and Drug Administration. June 28, 2011. Archived from the original on November 3, 2011.
  8. "38,000 more bottles of Lipitor recalled over odor complaints". CNN. October 30, 2010.
  9. "Lipitor (atorvastatin) 40 mg: Recall Specific Bottles". Drugs.com. December 23, 2010.
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