2,4,6-Tribromoanisole

2,4,6-TBA 2,4,6-trichlorobenzoic acid 2,4,6-Trichlorobenzoyl chloride changed changed 477210687 https://www.sigmaaldrich.com/US/en/product/aldrich/398780 2,4,6-Tribromoanisole Sigma-Aldrich 2,4,6-tribromoanisole.svg 150px Skeletal formula of 2,4,6-tribromoanisole 2,4,6-Tribromoanisole-3D-balls.png 160 Ball-and-stick model of the 2,4,6-tribromoanisole molecule 1,3,5-Tribromo-2-methoxybenzene Tribromoanisole; TBA changed chemspider 21170966 1/C7H5Br3O/c1-11-7-5(9)2-4(8)3-6(7)10/h2-3H,1H3 COc1c(Br)cc(Br)cc1Br changed chemspider 1S/C7H5Br3O/c1-11-7-5(9)2-4(8)3-6(7)10/h2-3H,1H3 changed chemspider YXTRCOAFNXQTKL-UHFFFAOYSA-N changed ?? 607-99-8 11839 correct FDA DO7M3M4LX5 COC1=C(C=C(C=C1Br)Br)Br 7 5 3 1 84 to 88 297 to 299 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.10.1021/jf030632f J Agric Food Chem 2004 52 5 1255–1262 Identification and responsibility of 2,4,6-tribromoanisole in musty, corked odors in wine Chatonnet P, Bonnet S, Boutou S, Labadie MD 14995130 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.2,4,6-Tribromoanisole: a Potential Cause of Mustiness in Packaged Food Whitfield, Frank B. Hill, Jodie L. Shaw, Kevin J. J. Agric. Food Chem. 1997 45 3 889–893 10.1021/jf960587u 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 winehttp://www.restek.com/Technical-Resources/Technical-Library/General-Interest/general_A031 Fast Screening of Recalled Tylenol for Tribromoanisole and Related Adulterants Using QuEChERS and GC-TOFMS Jason Thomas Jack Cochran amp 2010 Restek Corporation June 29, 2011 July 27, 2017 https://web.archive.org/web/20170727065722/http://www.restek.com/Technical-Resources/Technical-Library/General-Interest/general_A031 dead (or 3.4-7.9 ng/Lhttp://www.wawgg.org/files/documents/THK_&_Richard_Larsen_Tasting_Room_Training_power_point.pdf WAWGG Annual Meeting 2011: Tasting Room Staff Training Thomas Henick-Kling Richard Larsen amp Washington Association of Wine Grape Growers dead https://web.archive.org/web/20110929213420/http://www.wawgg.org/files/documents/THK_&_Richard_Larsen_Tasting_Room_Training_power_point.pdf September 29, 2011) 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.http://arthritis.webmd.com/news/20091229/tylenol-recall-expands Tylenol Recall Expands Daniel J. DeNoon December 29, 2009 WebMD Health Newshttps://www.fda.gov/Safety/Recalls/ucm261498.htm/ McNeil Consumer Healthcare Announces Voluntary Recall Of One Product Lot Of TYLENOL Extra Strength Caplets 225 Count Distributed In The U.S. June 28, 2011 Food and Drug Administration dead https://web.archive.org/web/20111103033823/https://www.fda.gov/Safety/Recalls/ucm261498.htm/ November 3, 2011 In this case, a supplier had used 2,4,6-tribromophenol to treat wooden pallets on which product packaging materials were transported and stored. In 2010 and in 2011, Pfizer recalled bottles of Lipitor after reports of an odor linked to the packaging bottles.http://www.cnn.com/2010/HEALTH/10/30/lipitor.recall/ 38,000 more bottles of Lipitor recalled over odor complaints October 30, 2010 CNN 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.https://www.drugs.com/fda/lipitor-atorvastatin-40-mg-recall-specific-bottles-12873.html Lipitor (atorvastatin) 40 mg: Recall Specific Bottles December 23, 2010 Drugs.com See also 2,4,6-Trichloroanisole References Category:Bromoarenes Category:Phenol ethers