The compounds causing cork taint and the factors affecting their transmission from cork to wine are discussed. These factors include: the solubilities of the taint compounds in wine, their affinity for the surface and the interior parts of the cork; their location on the surface of and within the closure; the rates at which they can migrate through the cork matrix; the volume of wine in contact with a closure(s); and whether taint transmission is taking place in bottled wine or with corks soaked in wine for screening purposes. 2,4,6‐Trichloroanisole (TCA) has been the primary topic of investigations reported in the general literature and is therefore the main focus of this article.
The compound responsible for a "fungal must" taint evident in industry assessments of wine corks was identified as 2-methoxy-3,5-dimethylpyrazine. The identification was made on the basis of gas chromatography/odor analyses, collection of material using micropreparative techniques, determination of chemical properties of collected material, and comparison by gas chromatography/mass spectrometry with an authentic sample, synthesized from 2-hydroxy-3,5-dimethylpyrazine. 2-Methoxy-3,5-dimethylpyrazine is an extremely potent compound with an unpleasant, musty, moldy aroma and an aroma threshold in a white wine of 2.1 ng/L. While its contribution to the frequency and intensity of cork taint in bottled wine is yet to be established, it has been assessed by some wine industry personnel as second only to 2,4,6-trichloroanisole as a cause of cork taint in Australian wine.
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 study was made of the response to components of pine oils and related compounds of antennae excised from female Sirex noctilio using electroantennogram (EAG) techniques. A response ratio of each compound was obtained after determining the response expected from the same amount of linalool, which was used as a reference material. Correlations were found between activity and chemical structure. Within each chemical class, compounds having a pinane skeleton and unsaturation showed the highest response. Activity differed between the cis-and trans-isomers of the same compound and waried according to the location of substituents with compounds possessing functional groups.
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