Corked Knee
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Cork taint is a broad term referring to a
wine fault 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 ...
characterized by a set of undesirable smells or tastes found in a bottle of
wine Wine is an alcoholic drink typically made from fermented grapes. Yeast consumes the sugar in the grapes and converts it to ethanol and carbon dioxide, releasing heat in the process. Different varieties of grapes and strains of yeasts are m ...
, especially spoilage that can only be detected after bottling,
aging Ageing ( BE) or aging ( AE) is the process of becoming older. The term refers mainly to humans, many other animals, and fungi, whereas for example, bacteria, perennial plants and some simple animals are potentially biologically immortal. In ...
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 Cork or CORK may refer to: Materials * Cork (material), an impermeable buoyant plant product ** Cork (plug), a cylindrical or conical object used to seal a container ***Wine cork Places Ireland * Cork (city) ** Metropolitan Cork, also known as G ...
stopper Stopper may refer to: * Bung, a plug used to stop the opening of a container ** Laboratory rubber stopper, a specific type of bung * Plug (sanitation), used to stop a drainage outlet * Defender (association football), in soccer (association footba ...
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 chief cause of cork taint is the presence of the chemical compounds 2,4,6-trichloroanisole (TCA) or 2,4,6-tribromoanisole (TBA) in the wine, which in many cases will have been transferred from the cork, but which also can have been transferred through the cork rather than from it. TCA is a compound which does not occur naturally. It is created when some
fungi A fungus ( : fungi or funguses) is any member of the 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, separately from ...
are treated with chlorinated phenolic compounds, which are a type of
antimicrobial An antimicrobial is an agent that kills microorganisms or stops their growth. Antimicrobial medicines can be grouped according to the microorganisms they act primarily against. For example, antibiotics are used against bacteria, and antifungals ar ...
agent used in the processing of wood. This compound is one of the chief factors responsible for the problem associated with
mold A mold () or mould () is one of the structures certain fungus, fungi can form. The dust-like, colored appearance of molds is due to the formation of Spore#Fungi, spores containing Secondary metabolite#Fungal secondary metabolites, fungal seco ...
liable to be found in cork. Very small amounts of this compound, on the order of nanograms, can be responsible for this defect. Corked wine containing TCA has a characteristic odor, variously described as resembling a moldy newspaper, wet dog, damp cloth, or damp basement. In almost all cases of corked wine the wine's native aromas are reduced significantly, and a very tainted wine is quite unpalatable, although 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 {{Unreferenced, date=March 2018 In general, detection is the action of accessing information without specific cooperation from with the sender. In the history of radio communications, the term "detector" was first used for a device that detected t ...
is also complicated by the
olfactory system The olfactory system, or sense of smell, is the sensory system used for smelling (olfaction). Olfaction is one of the special senses, that have directly associated specific organs. Most mammals and reptiles have a main olfactory system and an ac ...
's particularly quick
habituation Habituation is a form of non-associative learning in which an innate (non-reinforced) response to a stimulus decreases after repeated or prolonged presentations of that stimulus. Responses that habituate include those that involve the intact org ...
to TCA, making the smell less obvious on each subsequent sniff.


Production

The production of TCA in cork or its transfer by other means into wine is complex, but most results when naturally occurring airborne
fungi A fungus ( : fungi or funguses) is any member of the 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, separately from ...
are presented with
chlorophenol A chlorophenol is any organochloride of phenol that contains one or more covalently bonded chlorine atoms. There are five basic types of chlorophenols (mono- to pentachlorophenol) and 19 different chlorophenols in total when positional isomerism is ...
compounds, which they then convert into chlorinated
anisole Anisole, or methoxybenzene, is an 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. The compound is ...
derivatives. Chlorophenols taken up by cork trees are an industrial pollutant found in many
pesticide Pesticides are substances that are meant to control pests. This includes herbicide, insecticide, nematicide, molluscicide, piscicide, avicide, rodenticide, bactericide, insect repellent, animal repellent, microbicide, fungicide, and lampri ...
s and wood
preservative A preservative is a substance or a chemical that is added to products such as food products, beverages, pharmaceutical drugs, paints, biological samples, cosmetics, wood, and many other products to prevent decomposition by microbial growth or by ...
s, which may mean that the incidence of cork taint has risen in modern times. Chlorophenols can also be a product of the
chlorine Chlorine is a chemical element with the Symbol (chemistry), symbol Cl and atomic number 17. The second-lightest of the halogens, it appears between fluorine and bromine in the periodic table and its properties are mostly intermediate betwee ...
bleaching process used to sterilize corks (not in use anymore); this has led to the increasing adoption of methods such as
peroxide In chemistry, peroxides are a group of compounds with the structure , where R = any element. The group in a peroxide is called the peroxide group or peroxo group. The nomenclature is somewhat variable. The most common peroxide is hydrogen p ...
bleaching. TCA and TBA are 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 Guaiacol () is an organic compound with the formula C6H4(OH)(OCH3). It is a phenolic compound containing an methoxy functional group. Guaiacol appears as a viscous colorless oil, although aged or impure samples are often yellowish. It occurs wid ...
,
geosmin Geosmin ( ) is an irregular sesquiterpenoid, produced from the universal sesquiterpene precursor farnesyl pyrophosphate (also known as farnesyl diphosphate), in a two-step -dependent reaction. Geosmin, along with the irregular monoterpene 2-met ...
, 2-methylisoborneol (MIB), octen-3-ol and also octen-3-one - each has its own aroma, all of them considered objectionable in wine.


Estimated occurrence and industry response

The cork-industry group APCOR cites a study showing a 0.7–1.2% taint rate. In a 2005 study of 2800 bottles tasted at the ''
Wine Spectator ''Wine Spectator'' is an American lifestyle magazine that focuses on wine and wine culture, and gives out ratings to certain types of wine. It publishes 15 issues per year with content that includes news, articles, profiles, and general entertain ...
'' blind-tasting facilities in Napa, California, 7% of the bottles were found to be tainted. In 2013, the Cork Quality Council ran over 25 thousand tests. The results, compared with data from eight years ago, show a sharp reduction in TCA levels, of around 81 percent. In the last test, 90 percent of samples of natural cork stopper shipments showed values of under 1.0 ppt and only 7 percent had showed results of 1.0–2.0 ppt. 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 Controversy is a state of prolonged public dispute or debate, usually concerning a matter of conflicting opinion or point of view. The word was coined from the Latin ''controversia'', as a composite of ''controversus'' – "turned in an opposite d ...
in the winemaking community, with traditional cork growers on one side and the makers of newer synthetic closures and screw caps on the other. Screw caps and synthetic corks, however, are thought to be prone to another aroma taint: sulphidisation. This may arise from the reduced oxygen supply which concentrates sulphurous smells arising from wines with universal preservatives, however it is more likely that these wines contain excessive/imbalanced amounts of sulphite based preservatives to begin with.


Systemic TCA

Systemic TCA tainting occurs when TCA has infiltrated a winery via means other than cork and can affect the entire production of wine instead of just a few bottles. This occurs when
wine barrel Oak is used in winemaking to vary the color, flavor, tannin profile and texture of wine. It can be introduced in the form of a barrel during the fermentation or aging periods, or as free-floating chips or staves added to wine fermented in a vess ...
s, drain pipes, wooden beams in the cellars, or rubber hoses are tainted by TCA. Sometimes entire cellars have to be rebuilt in order to eliminate all potential systemic TCA culprits.
Rubber Rubber, also called India rubber, latex, Amazonian rubber, ''caucho'', or ''caoutchouc'', as initially produced, consists of polymers of the organic compound isoprene, with minor impurities of other organic compounds. Thailand, Malaysia, and ...
hoses or
gasket Some seals and gaskets A gasket is a mechanical seal which fills the space between two or more mating surfaces, generally to prevent leakage from or into the joined objects while under compression. It is a deformable material that is used to c ...
s 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 Bentonite () is an absorbent swelling clay consisting mostly of montmorillonite (a type of smectite) which can either be Na-montmorillonite or Ca-montmorillonite. Na-montmorillonite has a considerably greater swelling capacity than Ca-mon ...
, a swelling clay preparation (
smectite A smectite (from ancient Greek ''σμηκτός'' smektos 'lubricated'; ''σμηκτρίς'' smektris 'walker's earth', 'fuller's earth'; rubbing earth; earth that has the property of cleaning) is a mineral mixtures of various swelling sheet sil ...
) 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 this systemic TCA will often 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 the additional contribution of 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 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 clear to yellowish crysta ...
), an anti-microbial agent used in processing wood. Molds (and some suspect bacteria such as
Streptomyces ''Streptomyces'' is the largest genus of Actinomycetota and the type genus of the family Streptomycetaceae. Over 500 species of ''Streptomyces'' bacteria have been described. As with the other Actinomycetota, streptomycetes are gram-positive, ...
) are able to de-toxify TCP by methylating the -OH to -OCH3, which is not toxic. Chlorinated phenols can form chemically when
hypochlorous acid Hypochlorous acid (HClO, HOCl, or ClHO) is a weak acid that forms when chlorine dissolves in water, and itself partially dissociates, forming hypochlorite, ClO−. HClO and ClO− are oxidizers, and the primary disinfection agents of chlorine so ...
(HOCl, one of the active forms of
chlorine Chlorine is a chemical element with the Symbol (chemistry), symbol Cl and atomic number 17. The second-lightest of the halogens, it appears between fluorine and bromine in the periodic table and its properties are mostly intermediate betwee ...
) or chlorine radicals come in contact with wood (untreated, such as
barrel A barrel or cask is a hollow cylindrical container with a bulging center, longer than it is wide. They are traditionally made of wooden staves and bound by wooden or metal hoops. The word vat is often used for large containers for liquids, ...
s or
pallet A pallet (also called a skid) 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 foundat ...
s.) The use of chlorine or other halogen-based sanitizing agents is being phased out of the wine industry in favor of
peroxide In chemistry, peroxides are a group of compounds with the structure , where R = any element. The group in a peroxide is called the peroxide group or peroxo group. The nomenclature is somewhat variable. The most common peroxide is hydrogen p ...
or
peracetic acid Peracetic acid (also known as peroxyacetic acid, or PAA) is an organic compound with the formula CH3CO3H. This peroxy acid is a colorless liquid with a characteristic acrid odor reminiscent of acetic acid. It can be highly corrosive. Peracetic a ...
preparations.
Chlorine dioxide Chlorine dioxide is a chemical compound with the formula ClO2 that exists as yellowish-green gas above 11 °C, a reddish-brown liquid between 11 °C and −59 °C, and as bright orange crystals below −59 °C. It is usually ...
has not been shown to produce these spontaneous
chlorophenol A chlorophenol is any organochloride of phenol that contains one or more covalently bonded chlorine atoms. There are five basic types of chlorophenols (mono- to pentachlorophenol) and 19 different chlorophenols in total when positional isomerism is ...
s. Chlorine dioxide is a relatively new agent being used in the wine industry due to its obvious advantages, having shown no evidence of the possibility of TCA formation. ''Wine Spectator'' has reported that such
California wine California wine production has a rich viticulture history since 1680 when Spanish Jesuit missionaries planted ''Vitis vinifera'' vines native to the Mediterranean region in their established missions to produce wine for religious services. I ...
ries as Pillar Rock Vineyard,
Beaulieu Vineyard Beaulieu Vineyard (BV for labelling purposes) is a vineyard near Rutherford, California, belonging to the appellation Rutherford AVA. It was established by Georges de Latour and his wife Fernande in 1900. History Initially a purchase of of la ...
, and
E & J Gallo Winery E & J Gallo Winery is a winery and distributor headquartered in Modesto, California. It was founded in 1933 by Ernest Gallo and Julio Gallo, and is the largest exporter of California wines. E & J Gallo Winery is the largest family-owned wine ...
have had trouble with systemic TCA.


Treatment

Filtration Filtration is a physical separation process that separates solid matter and fluid from a mixture using a ''filter medium'' that has a complex structure through which only the fluid can pass. Solid particles that cannot pass through the filter ...
and purification systems now exist that attempt to remove the TCA from corked wine to make it drinkable again, though there are few means of reducing the level of TCA in tainted wine that are approved by the TTB (formerly BATF). One method of removing TCA from tainted wine is to soak
polyethylene Polyethylene or polythene (abbreviated PE; IUPAC name polyethene or poly(methylene)) is the most commonly produced plastic. It is a polymer, primarily used for packaging ( plastic bags, plastic films, geomembranes and containers including bo ...
(a plastic used for applications such as milk containers and plastic food wrap) in the affected 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 the alcohol level of the wine. This can be done at home, as advocated by Andrew Waterhouse, professor of
wine chemistry 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 ...
at
University of California, Davis The University of California, Davis (UC Davis, UCD, or Davis) is a public land-grant research university near Davis, California. Named a Public Ivy, it is the northernmost of the ten campuses of the University of California system. The institut ...
, by pouring the wine into a bowl with a sheet of polyethylene
plastic wrap Plastic wrap, cling film, Saran wrap, cling wrap, Glad wrap or food wrap is a thin plastic film typically used for sealing food items in containers to keep them fresh over a longer period of time. Plastic wrap, typically sold on rolls in boxes ...
. For ease of pouring, a
pitcher In baseball, the pitcher is the player who throws ("pitches") the baseball from the pitcher's mound toward the catcher to begin each play, with the goal of retiring a batter, who attempts to either make contact with the pitched ball or draw ...
,
measuring cup A measuring cup is a kitchen utensil used primarily to measure the volume of liquid or bulk solid cooking ingredients such as flour and sugar, especially for volumes from about 50  mL (2  fl oz) upwards. Measuring cups are also used ...
, or
decanter A decanter is a vessel that is used to hold the decantation of a liquid (such as wine) which may contain sediment. Decanters, which have a varied shape and design, have been traditionally made from glass or crystal. Their volume is usually equ ...
can be used instead. The 2,4,6-trichloroanisole will stick to the plastic. The process is effective within a few minutes. Some vintners have used the so-called ''
half and half "Half and half" is the name of various beverages and foods made of an equal-parts mixture of two substances, including dairy products, alcoholic beverages, and soft drinks. Alcoholic beverages Belgium In some cafés in Brussels, a "half en ...
'' mix of
milk Milk is a white liquid food produced by the mammary glands of mammals. It is the primary source of nutrition for young mammals (including breastfed human infants) before they are able to digestion, digest solid food. Immune factors and immune ...
and
cream Cream is a dairy product composed of the higher-fat layer skimmed from the top of milk before homogenization. In un-homogenized milk, the fat, which is less dense, eventually rises to the top. In the industrial production of cream, this process ...
to remove TCA from wine (the TCA in the wine is sequestered by the
butterfat Butterfat or milkfat is the fatty portion of milk. Milk and cream are often sold according to the amount of butterfat they contain. Composition Butterfat is mainly composed of triglycerides. Each triglyceride contains three fatty acids. Butt ...
in ''half and half''). The French company Embag markets a product called "Dream Taste"http://www.dream-taste-international.com/ which uses a
copolymer In polymer chemistry, a copolymer is a polymer derived from more than one species of monomer. The polymerization of monomers into copolymers is called copolymerization. Copolymers obtained from the copolymerization of two monomer species are some ...
shaped like a cluster of grapes to remove the TCA taint from wine.


See also

*
Alternative wine closure Alternative wine closures are substitute closures used in the wine industry for sealing wine bottles in place of traditional cork closures. The emergence of these alternatives has grown in response to quality control efforts by winemakers to pr ...
*
Flavor scalping Flavor scalping is a term used in the packaging industry to describe the loss of quality of a packaged item due to either its volatile flavors being absorbed by the packaging or the item absorbing undesirable flavors from its packaging. A class ...
*
Wine fault 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 ...


Notes


References

* * *


External links

* {{Authority control Wine terminology Oenology Wine packaging and storage