2,4,6-Tribromoanisole
Encyclopedia
2,4,6-Tribromoanisole 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 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.
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 pesticide
s and wood preservative
s. 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.
voluntarily recalled some over-the-counter products including Tylenol due to an odor caused by tribromoanisole. In this case, 2,4,6-tribromophenol
was used 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. 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.
Bromine
Bromine ") is a chemical element with the symbol Br, an atomic number of 35, and an atomic mass of 79.904. It is in the halogen element group. The element was isolated independently by two chemists, Carl Jacob Löwig and Antoine Jerome Balard, in 1825–1826...
derivative of anisole
Anisole
Anisole, or methoxybenzene, is the organic compound with the formula CH3OC6H5. It is a colorless liquid with a smell reminiscent of anise seed, and in fact many of its derivatives are found in natural and artificial fragrances...
. It is one of the chemicals responsible for cork taint
Cork taint
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...
.
Tribromoanisole is a fungal metabolite
Metabolite
Metabolites are the intermediates and products of metabolism. The term metabolite is usually restricted to small molecules. A primary metabolite is directly involved in normal growth, development, and reproduction. Alcohol is an example of a primary metabolite produced in large-scale by industrial...
of 2,4,6-tribromophenol
2,4,6-Tribromophenol
2,4,6-Tribromophenol 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.- Production :...
, which is used as a fungicide in place of the banned pentachlorophenol
Pentachlorophenol
Pentachlorophenol is an organochlorine compound used as a pesticide and a disinfectant. First produced in the 1930s, it is marketed under many trade names...
. 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.
Tribromoanisole is usually produced when naturally occurring airborne fungi
Fungus
A fungus is a member of a large group of eukaryotic organisms that includes microorganisms such as yeasts and molds , as well as the more familiar mushrooms. These organisms are classified as a kingdom, Fungi, which is separate from plants, animals, and bacteria...
and/or bacteria
Bacteria
Bacteria are a large domain of prokaryotic microorganisms. Typically a few micrometres in length, bacteria have a wide range of shapes, ranging from spheres to rods and spirals...
(usually Aspergillus
Aspergillus
Aspergillus is a genus consisting of several hundred mold species found in various climates worldwide. Aspergillus was first catalogued in 1729 by the Italian priest and biologist Pier Antonio Micheli...
sp., Penicillium
Penicillium
Penicillium is a genus of ascomycetous fungi of major importance in the natural environment as well as food and drug production. Members of the genus produce penicillin, a molecule that is used as an antibiotic, which kills or stops the growth of certain kinds of bacteria inside the body...
sp., Actinomycetes, Botrytis cinerea
Botrytis cinerea
Botrytis cinerea is a necrotrophic fungus that affects many plant species, although its most notable hosts may be wine grapes. In viticulture, it is commonly known as botrytis bunch rot; in horticulture, it is usually called grey mould or gray mold.The fungus gives rise to two different kinds of...
, Rhizobium
Rhizobium
Rhizobium is a genus of Gram-negative soil bacteria that fix nitrogen. Rhizobium forms an endosymbiotic nitrogen fixing association with roots of legumes and Parasponia....
sp., or Streptomyces
Streptomyces
Streptomyces is the largest genus of Actinobacteria and the type genus of the family Streptomycetaceae. Over 500 species of Streptomyces bacteria have been described. As with the other Actinobacteria, streptomycetes are gram-positive, and have genomes with high guanine and cytosine content...
) are presented with brominated phenolic compounds, which they then convert into bromoanisole
Bromoanisole
Bromoanisole, also known as para-bromoanisole or 1-bromo-4-methoxybenzene, is a clear liquid with a pleasant smell similar to that of anise seed....
derivatives. The bromophenols can originate from various contaminants including those found in some pesticide
Pesticide
Pesticides are substances or mixture of substances intended for preventing, destroying, repelling or mitigating any pest.A pesticide may be a chemical unicycle, biological agent , antimicrobial, disinfectant or device used against any pest...
s and wood preservative
Preservative
A preservative is a naturally occurring or synthetically produced substance that is added to products such as foods, pharmaceuticals, paints, biological samples, wood, etc. to prevent decomposition by microbial growth or by undesirable chemical changes....
s. They can also migrate from other objects such as shipping pallets treated by bromophenols.
Tribromoanisole has a very low odor detection threshold
Odor detection threshold
The odor detection threshold is the lowest concentration of a certain odor compound that is perceivable by the human sense of smell. The thresholds of a chemical compound is determined in part by its shape, polarity, partial charges and molecular mass...
. 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
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 & JohnsonJohnson & Johnson
Johnson & Johnson is an American multinational pharmaceutical, medical devices and consumer packaged goods manufacturer founded in 1886. Its common stock is a component of the Dow Jones Industrial Average and the company is listed among the Fortune 500....
voluntarily recalled some over-the-counter products including Tylenol due to an odor caused by tribromoanisole. In this case, 2,4,6-tribromophenol
2,4,6-Tribromophenol
2,4,6-Tribromophenol 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.- Production :...
was used 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. 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.