Names | |
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Preferred IUPAC name 1,3,5-Tribromo-2-methoxybenzene | |
Other names Tribromoanisole; TBA | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
ECHA InfoCard | 100.156.226 |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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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). |
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. 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.
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]
Tylenol is a brand of medication, advertised for reducing pain, reducing fever, and relieving the symptoms of allergies, cold, cough, headache, and influenza. The active ingredient of its original flagship product is paracetamol, an analgesic and antipyretic. Like the words paracetamol and acetaminophen, the brand name Tylenol is derived from a chemical name for the compound, N-acetyl-para-aminophenol (APAP). The brand name is owned by McNeil Consumer Healthcare, a subsidiary of Johnson & Johnson.
Cork taint is a broad term referring to a wine fault characterized by a set of undesirable smells or tastes found in a bottle of wine, especially spoilage that can only be detected after bottling, aging and opening. Though modern studies have shown that other factors can also be responsible for taint – including wooden barrels, storage conditions and the transport of corks and wine – the cork stopper is normally considered to be responsible, and a wine found to be tainted on opening is said to be corked or "corky". Cork taint can affect wines irrespective of price and quality level.
The Chicago Tylenol murders were a series of poisoning deaths resulting from drug tampering in the Chicago metropolitan area in 1982. The victims had all taken Tylenol-branded acetaminophen capsules that had been laced with potassium cyanide. A total of seven people died in the original poisonings, with several more deaths in subsequent copycat crimes.
Ranbaxy Laboratories Limited was an Indian multinational pharmaceutical company that was incorporated in India in 1961 and remained an entity until 2014. The company went public in 1973. Ownership of Ranbaxy changed twice over the course of its history.
Atorvastatin, sold under the brand name Lipitor among others, is a statin medication used to prevent cardiovascular disease in those at high risk and to treat abnormal lipid levels. For the prevention of cardiovascular disease, statins are a first-line treatment. It is taken by mouth.
Benadryl is a brand of various antihistamine medications used to stop allergies, whose content varies in different countries, but which includes some combination of diphenhydramine, acrivastine, and/or cetirizine.
A pallet is a flat transport structure, which supports goods in a stable fashion while being lifted by a forklift, a pallet jack, a front loader, a jacking device, or an erect crane. A pallet is the structural foundation of a unit load, which allows handling and storage efficiencies. Goods or shipping containers are often placed on a pallet secured with strapping, stretch wrap or shrink wrap and shipped. Since its invention in the twentieth century, its use has dramatically supplanted older forms of crating like the wooden box and the wooden barrel, as it works well with modern packaging like corrugated boxes and intermodal containers commonly used for bulk shipping.
Bottling lines are production lines that fill a product, generally a beverage, into bottles on a large scale. Many prepared foods are also bottled, such as sauces, syrups, marinades, oils and vinegars.
Excedrin is an over-the-counter headache pain reliever, typically in the form of tablets or caplets. It contains paracetamol (acetaminophen), aspirin, and caffeine. It was manufactured by Bristol-Myers Squibb until it was purchased by Novartis in July, 2005 along with other products from BMS's over-the-counter business. As of March 2015, GSK holds majority ownership of Excedrin through a joint venture transaction with Novartis. On 18 July 2022, GSK spun off its consumer healthcare business to Haleon.
2,4,6-Trichloroanisole (TCA) is a chemical compound that is a chlorinated derivative of anisole. TCA is a fungal metabolite of 2,4,6-trichlorophenol, which is used as a fungicide. It can be found in minute traces on packaging materials stored in the presence of fiberboard treated with trichlorophenol.
Rolaids is an American brand of calcium and magnesium-based antacid produced by Chattem. It was invented by American chemist Irvine W. Grote in the late 1920s, and originated with manufacturing in Chattanooga, Tennessee, under one of Chattem's forerunner companies, which manufactured the brand for Warner-Lambert; Warner-Lambert merged with Pfizer in 2000.
A wine fault or defect is an unpleasant characteristic of a wine often resulting from poor winemaking practices or storage conditions, and leading to wine spoilage. Many of the compounds that cause wine faults are already naturally present in wine but at insufficient concentrations to be of issue. In fact, depending on perception, these concentrations may impart positive characters to the wine. However, when the concentration of these compounds greatly exceeds the sensory threshold, they replace or obscure the flavors and aromas that the wine should be expressing. Ultimately the quality of the wine is reduced, making it less appealing and sometimes undrinkable.
Grapefruit mercaptan is the common name for a natural organic compound found in grapefruit. It is a monoterpenoid that contains a thiol functional group. Structurally a hydroxy group of terpineol is replaced by the thiol in grapefruit mercaptan, so it also called thioterpineol. Volatile thiols typically have very strong, often unpleasant odors that can be detected by humans in very low concentrations. Grapefruit mercaptan has a very potent, but not unpleasant, odor, and it is the chemical constituent primarily responsible for the aroma of grapefruit. This characteristic aroma is a property of only the R enantiomer.
1-Butanol, also known as butan-1-ol or n-butanol, is a primary alcohol with the chemical formula C4H9OH and a linear structure. Isomers of 1-butanol are isobutanol, butan-2-ol and tert-butanol. The unmodified term butanol usually refers to the straight chain isomer.
Dogs, as with all mammals, have natural odors. Natural dog odor can be unpleasant to dog owners especially when dogs are kept inside the home, as some people are not used to being exposed to the natural odor of a non-human species living in proximity to them. Dogs may also develop unnatural odors as a result of skin disease or other disorders or may become contaminated with odors from other sources in their environment.
2,4,6-Tribromophenol (TBP) is a brominated derivative of phenol. It is used as a fungicide, as a wood preservative, and an intermediate in the preparation of flame retardants.
Condensed tannins are polymers formed by the condensation of flavans. They do not contain sugar residues.
Wine is a complex mixture of chemical compounds in a hydro-alcoholic solution with a pH around 4. The chemistry of wine and its resultant quality depend on achieving a balance between three aspects of the berries used to make the wine: their sugar content, acidity and the presence of secondary compounds. Vines store sugar in grapes through photosynthesis, and acids break down as grapes ripen. Secondary compounds are also stored in the course of the season. Anthocyanins give grapes a red color and protection against ultraviolet light. Tannins add bitterness and astringency which acts to defend vines against pests and grazing animals.
6-Nonenal is an organic compound with the formula C2H5CH=CH(CH2)4CHO. Other isomeric nonenal compounds are also known to exist naturally, e.g. 2-nonenal. The cis-isomer of 6-nonenal is often listed as the principal component in the aromas of muskmelon fruits. The trans-isomer is listed as an off-flavor aroma of milk foams, and thought to be a possible polypropylene odorant.
Packaging machinery is used throughout all packaging operations, involving primary packages to distribution packs. This includes many packaging processes: fabrication, cleaning, filling, sealing, combining, labeling, overwrapping, palletizing.