Origin and fate of 2,4,6-trichloroanisole in cork bark and wine corks

Abstract

2,4,6‐Trichloroanisole (TCA), which is a major cause of cork taint in bottled wine, is already present in the bark of living cork trees to the extent that it can account for the majority of incidences of cork taint in bottled wine. Other post‐harvest sources of TCA are known and may add to the forest‐derived TCA in cork. Both the origin of TCA in the bark in the forest, and the means by which additional TCA can accumulate in the corks during manufacture, have been examined. TCA can originate from 2,4,6‐trichlorophenol (TCP) produced from naturally‐occurring phenol and chlorine from sanitisers and cleaning products, and town water. Also, chlorophenol biocides have accumulated in the environment due to the large quantities used in previous times – TCP has been a minor impurity in pentachlorophenol biocides and a major ingredient in other preparations. There is some evidence that chlorophenols were used in pest management in the forest prior to restrictions on the use of these materials. The factors affecting the uptake and loss of TCA by the bark on the tree and by corks during production, and through to their use in the bottling of wine have been considered in this review.

A rapid space-resolved solid-phase microextraction method as a powerful tool to determine contaminants in wine based on their volatility

“…Cork taint in wine has been one of the most serious problems confronting the modern wine industry (Pena-Neira et al, 2000;Simpson, 1990;Simpson & Sefton, 2007), causing economic loss and occasionally damaging the reputation of the winery which is unfortunate enough, to experience such a major problem. The defect in the cork stoppers is primarily attributed to the presence of 2,4,6-trichloroanisole (Buser, Zanier, & Tanner, 1982) (in at least 80% of the cases).…”

Simple approach for cleaning up 2,4,6‐trichloroanisole from alcoholic‐beverage‐reconstituted solutions using polymeric materials

“…2,4,6‐Trichlorophenol is a product of the microbiological methylation of chlorophenols coming from chlorine treatment (Simpson and Sefton ), but can also be generated by dismantling of more highly chlorinated compounds (tetra‐ and penta‐chlorophenols). These precursors of haloanisoles are used in products, such as sanitisers, wood preservatives and biocides, which can accumulate in the environment.…”

“…These precursors of haloanisoles are used in products, such as sanitisers, wood preservatives and biocides, which can accumulate in the environment. The generation of chlorine compounds through Basidiomycetes and Penicillium isolates are also mentioned (Simpson and Sefton ). For example, some Basidiomycetes can convert chlorophenols to their respective haloanisoles, where the effectiveness of this bioconversion will depend on the strain of the microorganism.…”

The effectiveness of electron beam irradiation to reduce or eliminate mould in cork stoppers

“…Due to high levels of cork contaminated with TCA, as much as 40% in reported cases, a search for alternative wine bottle closures has substantially grown in the past fifteen years (Sefton & Simpson, ). TCA forms when one or more of the fungal strains known to cause TCA comes into cont‐act with 2,4,6‐trichlorophenol (TCP) and through O‐methylation changes TCP into TCA (Simpson & Sefton, ). TCA is the most common and odoriferous of the six cork taints.…”