Anisole trichloro

Evans, T.J., Butzke, C.E., and Ebeler S.E. (1997). Analysis of 2,4,6-trichloro-anisole in wines using solid-phase microextraction coupled to gas chromatography-mass spectrometry, J. Chromatogr. A, 786,293-298. 

Wine drinkers sometimes find that a bottle is corked. This means that a defective cork has leached trichloro-anisole, or TCA, into the wine. This compound ruins the wine, making it smell like wet cardboard. Some wine collectors report that as much as 20% of the bottles they open are corked, while others hardly ever encounter the problem. How would you account for the individual differences How could the problem of corked wines be solved ... 

Bulit, J. and R. Lafon. 1970. Quelques aspects de la Biologic du Botrytis cinerea Pers. agent de la pourriture grise des raisins. Conn. Vigne Vin 4 159-174. Buser, H.R., C. Zanier, and H. Tanner. 1982. Identification of 2,4,6-trichloro-anisole as a potent compound causing cork taint in wine. J. Agric. Food Chem. 30 359-362. 

A microbial conversion of sensory significance already discussed to some extent is the conversion of phenols to chloroanisoles (airborne taints). A defect in wine recognized as cork taint is considered to be primarily due to this conversion. It was estimated that cork taint results in the rejection of 2 to 6% of commercial wines [146]. While this reference is somewhat dated, it is of relevance that this is the second most researched (based on number of pubUcations) sensory defect in foods (after boar taint), which suggests that the defect is still of importance to the industry. Chloroanisoles can be formed from the microbial conversion of pentachlorophenol (a component of some insecticides and wood preservatives) in the cork or from hypochlorite treated corks (forms chlorophenols) with subsequent microbial methyl-ation to the anisoles. In either event, the chloroanisoles (primarily 2,4,6-trichloro-anisole) are formed on/in the cork and leach into the wine [127]. This has lead to a movement within the wine industry to use synthetic bottle stoppers in place of cork. 

Organic compounds sought include naturally derived materials, such as mycotoxins and off-flavours (produced by rancidification or spoilage), and man-made/industrial chemicals, e.g. pesticides, veterinary drugs, environmental contaminants (such as polychlorodibenzo-p-dioxins, polychlorinated biphenyls, polynuclear aromatic hydrocarbons, etc.) and food tainting compounds (e.g. 2,4,6-trichloro-anisole, the compound responsible for musty cork taint in wine, arising from the inappropriate use of wood preservatives). GC-MS and HPLC-API-MS are widely used for these types of analyses. Desirable food components present at trace levels, such as nutrients, are also determined using these techniques. 

Of numerous chloral condensations with aromatic hydrocarbons the most interesting for the synthesis of condensation monomers are the reactions with benzene [3], toluene [4], acenaphthene [5], phenol [6], anisol [7], acetanilide [8] and halobenzenes like chlorobenzene [9] and fluorobenzene [10]. In general terms, these reactions proceed according to Scheme 2.2 and give the desired 1,1,1-trichloro-... 

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