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2,4,6-Trichloroanisole
IUPAC name	2,4,6-Trichloroanisole
Identifiers
CAS number	87-40-1
RTECS number	MFCD00000588
SMILES	COc1c(Cl)cc(Cl)cc1Cl
Properties
Molecular formula	C7H5OCl3
Molar mass	211.47 g/mol
Density	? g/cm3
Melting point	60-62 °C
Boiling point	140 °C at 28 torr
Hazards
R-phrases	Template:R22-36
S-phrases	S26
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Cork taint is a broad term referring to 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 transportation of corks and wine – the cork is normally considered to be responsible, and a wine found to be tainted on opening is said to be "corked".

The chief cause of cork taint is the presence of 2,4,6-trichloroanisole (TCA) in the wine. Corked wine containing TCA has a characteristic odor, variously described as resembling a moldy newspaper, wet dog, or damp basement. In almost all cases of corked wine the wine's native aromas are reduced significantly, and a very tainted wine is completely undrinkable (though harmless). While the human threshold for detecting TCA is measured in the single-digit parts per trillion, this can vary by several orders of magnitude depending on an individual's sensitivity. Detection is also complicated by the olfactory system's particularly quick habituation to TCA, making the smell less obvious on each subsequent sniff.

The production of TCA in wine is complex, but most results when naturally-occurring airborne fungi are presented with chlorophenol compounds, which they then convert into chloroanisole. Chlorphenols taken up by cork trees are an industrial pollutant found in many pesticides and wood preservatives, which may mean that the incidence of cork taint has risen in modern times. Chlorphenols can also be a product of the chlorine bleaching process ironically used to sterilise corks, which has led to the increasing adoption of methods such as peroxide bleaching.

TCA is responsible for the vast majority of cases of cork taint, but other less common and less known compounds that can cause different varieties include guaiacol, geosmin, 2-methylisoborneol (MIB), octen-3-ol and octen-3-one - each has its own aroma, all of them considered objectionable in wine.

The incidence of bottles with cork taint is estimated to be between 1 and 15 percent. The former figure is from the cork-industry group APCOR, which cites a study showing a 0.7-1.2% taint rate. Anecdotal evidence from wine professionals suggests that the rate may be substantially higher. In a 2005 study of 2800 bottles tasted at the Wine Spectator blind-tasting facilities in Napa, California, 7% of the bottles were found to be tainted.^[1]

Improvements in cork and winemaking methodology continue to strive to lower the incidence, but the media attention given to cork taint has created a controversy in winemaking, with traditional cork growers on one side and the makers of newer synthetic closures and screw caps (such as Alcan's Stelvin cap) on the other. Screw caps and synthetic corks, however, can be prone to another aroma taint: sulphidisation, which arises from the reduced oxygen supply which concentrates sulphurous smells arising from universal preservatives.^[2]

There are now filtration and purification systems available which attempt to remove the TCA from corked wine to make it drinkable again.

Systemic TCA tainting occurs when TCA has infiltrated a winery via means other than cork and can affect entire production of wine instead of just a few bottles. This occurs when wine barrels, drain pipes, wooden beams in the cellars, and rubber hoses are tainted by TCA. Sometimes entire cellars have to be rebuilt in order to extinguish all potential systemic TCA culprits. Rubber hoses or gaskets have a high affinity for TCA and therefore concentrate TCA from the atmosphere. Wine or water that subsequently passes through infected hoses can become tainted with TCA. Another possible means of TCA contamination is through the use of Bentonite, a clay preparation used in treating wine for heat stability. Bentonite has a high affinity for TCA and will absorb TCA and related chemicals in the atmosphere. If an open bag of Bentonite is stored in an environment with a high (1-2 ng/g or ppb) TCA concentration, this TCA will be absorbed in the Bentonite and transferred to the wine lot to which the Bentonite is added.

It is notable that often this systemic TCA will impart a trace (1-2 ng/L or ppt) to the wine, which itself is not detected by most consumers. However, with this high baseline level of TCA in bottled wine, even a relatively clean cork can elevate the TCA level in the wine above threshold levels (4-6 ng/L or ppt), rendering the wine "corked."

The primary chemical precursor to TCA is TCP (2,4,6-Trichlorophenol), an anti-microbial agent used in processing wood. Molds (and some suspect bacteria such as Streptomyces^[3]) are able to de-toxify TCP by methylating the -OH to -OCH3, which is not toxic. Chlorinated phenols can form chemically when hypochlorous acid (HOCl-, one of the active forms of chlorine) or chlorine radicals come in contact with wood (untreated, such as barrels or pallets.) The use of chlorine or other halogen-based sanitizing agents is being phased out of the wine industry in favor of peroxide or peracetic acid preparations. It should be noted that Chlorine dioxide has not been shown to produce these spontaneous chlorophenols. Wine Spectator has reported that such California wineries as Pillar Rock Vineyard, Beaulieu Vineyard, E & J Gallo Winery and Chateau Montelena have had trouble with Systematic TCA.^[4]

There are few means of reducing the level of TCA in tainted wine that are approved by the TTB (formerly BATF.) Some vintners have used Half & Half to remove TCA from wine (the TCA in the wine is sequestered by the butterfat in Half & Half). Other means of removing TCA from tainted wine is to soak polyethylene (a plastic used for applications such as milk containers and plastic food wrap) in the infected wine. The non-polar TCA molecule has a high affinity for the polyethylene molecule, thereby removing the taint from the wine. The surface area of polyethylene needed to reduce the taint to sub-threshold levels is based on the TCA level in the affected wine, temperature, and% Alcohol of the wine. The French company Boffin markets a product called "Dream Taste" which uses a copolymer shaped like a cluster of grapes to remove the TCA taint from commercial wine.

• Alternative wine closures
• Flavor scalping
• Wine fault

• Buser HR, Zanier C, Tanner H (1982). "Identification of 2,4,6-Trichloroanisole as a Potent Compound Causing Cork Taint in Wine". Journal of Agricultural and Food Chemistry 30: 359-382.  DOI
• Tindale CR, Whitefield FB, Levingston SD, Nguyen THL (1989). "Fungi Isolated from Packing Materials - Their Role in the Production of 2,4,6-Trichloroanisole". Journal of Science of Food and Agriculture 49: 437-447. 
• Pirbazari M, Borow HS, Craig S, Ravindran V, McGuire MJ (1992). "Physical-Chemical Characterization of 5 Earth-Musty-Smelling Compounds". Water Science and Technology 25: 81-88. 

1. ^ Wine Spectator March 31st, 2006
2. ^ BBC News Magazine Website
3. ^ Bacterial Causes of Winery Chloroanisole Contamination Paula A. Mara and Linda F. Bisson, Papers and Posters Presented at the ASEV 56th Annual Meeting 22–24 June 2005, Seattle, Washington
4. ^ J. Laube Taint Misbehavin Wine Spectator pg 43 March 31st, 2007

• Article on corked wine