2,4,6-Trichloroanisole (TCA) is a chemical compound that is a chlorinated

Chlorine

Chlorine is the chemical element with atomic number 17 and symbol Cl. It is the second lightest halogen, found in the periodic table in group 17. The element forms diatomic molecules under standard conditions, called dichlorine...

 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...

.
Trichloroanisole 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-trichlorophenol

2,4,6-Trichlorophenol

2,4,6-Trichlorophenol, also known as TCP, phenaclor, Dowicide 2S, Dowcide 2S, omal, is a chlorinated phenol that has been used as a fungicide, herbicide, insecticide, antiseptic, defoliant, and glue preservative. It is a yellow solid with a strong, sweet odour...

, 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.

TCA is the chemical primarily 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...

 in wines. TCA has also been implicated as a major component of the "Rio defect" in coffees from Central and South America.

Trichloroanisole 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 chlorinated

Chlorination

Chlorination is the process of adding the element chlorine to water as a method of water purification to make it fit for human consumption as drinking water...

 phenolic compounds, which they then convert into chlorinated 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...

 derivatives. The chlorophenols can originate from various contaminants such as 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. Chlorophenols can also be a product of the chlorine

Chlorine

Chlorine is the chemical element with atomic number 17 and symbol Cl. It is the second lightest halogen, found in the periodic table in group 17. The element forms diatomic molecules under standard conditions, called dichlorine...

 bleaching process used to sterilize

Sterilization (microbiology)

Sterilization is a term referring to any process that eliminates or kills all forms of microbial life, including transmissible agents present on a surface, contained in a fluid, in medication, or in a compound such as biological culture media...

 or bleach

Bleach

Bleach refers to a number of chemicals that remove color, whiten, or disinfect, often via oxidation. Common chemical bleaches include household chlorine bleach , lye, oxygen bleach , and bleaching powder...

 wood, paper, and other materials; they can be synthetized by reaction of hypochlorite

Hypochlorite

The hypochlorite ion, also known as chlorate anion is ClO−. A hypochlorite compound is a chemical compound containing this group, with chlorine in oxidation state +1.Hypochlorites are the salts of hypochlorous acid...

s with lignin

Lignin

Lignin or lignen is a complex chemical compound most commonly derived from wood, and an integral part of the secondary cell walls of plants and some algae. The term was introduced in 1819 by de Candolle and is derived from the Latin word lignum, meaning wood...

. They can also migrate from other objects such as shipping pallets treated by chlorophenols.

Trichloroanisole 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...

(single parts per trillion), so even very minute amounts can be detected. It causes unpleasant earthy, musty and moldy aromas.