Sunday, June 17, 2012

The Chemistry of Cork Taint


            What is cork taint, and where does it come from? I have personally never experienced or even heard of it, but when the enologist was talking about it at Barone Ricasoli vineyards, I became intrigued.  It turns out that the Ricasoli winery actually tests many different types of corks to see which ones have the best properties for their wine.  If more than a couple of the corks from the batch they ordered are not up to par, they send the entire order back.  Who knew such an innocuous piece of wood could ruin a good bottle of wine?
TCA
TBA
            As it turns out, there are two main chemicals that are found to be present in wine with cork taint: 2,4,6-trichloroanisole (TCA) and 2,4,6-tribromoanisole (TBA).  These chemicals are responsible for the moldy, damp, or mildewy smells associated with cork taint in a bottle of wine.  These chemicals can be introduced into the bottle of whine by or through the cork.  There are also cases of systematic TCA introduction, in which case TCA affects an entire production line of wine.  Although the cork is almost always blamed for wine taint, wine spoilage can also arise from oxidation in the wine, unclean processing equipment, and bacteria.
            The corks that cause cork taint often contain chlorophenol that the cork tree has taken up through the industrially polluted air (This just gives us another good reason to be more environmentally conscious; we’ll have less ruined wine!).  These chlorophenols can also be introduced into the cork through the bleaching and sterilization process that they must undergo before use.  These chlorophenols in the cork then come into contact with natural, airborne fungi that convert the chlorophenols into taint-producing TCA.
Production Process of TCA

            One of the solutions to cork taint that has been proposed is the use of synthetic closures, like rubber corks.  However, this is not the best solution because the rubber corks cause problems of their own.  Rubber corks often taint the aroma of the wine due to sulphidisation, which occurs because not enough oxygen can get into the wine through the rubber cork.  This does not happen as often in wood-corked wine because the wood cork can act as a microfilter that allows oxygen and other small molecules into the wine.  The process is very similar to wine aging in wooden barrels to allow small molecules to diffuse in and out of the wine.
            There is no real way to stop wine taint other than by testing the corks to be used in the wine before corking an entire production line with them.  There are ways to remove the unpleasantness from a batch of tainted wine if it had been systematically tainted.  To do this, wineries (and you too, if you encounter this problem) can soak something made of polyethylene, like a milk jug, in the wine.  The polyethylene attracts the nonpolar TCA molecules, which can attach to the polyethylene to be removed when the plastic is removed.
            Any way you look at it, tainted wine, especially if it’s that expensive bottle you were excited about drinking, is no fun.  There is not much that we can do to prevent wine tainting other than through testing, and perhaps by decreasing pollution around cork trees (and everywhere else).  In spite of that, at least we have a simple way of remedying the solution in our own homes when we sit down, open a bottle of wine, and smell something like moldy newspaper coming out of the bottle.



http://www.chemicalbook.com/ChemicalProductProperty_EN_CB7375976.htm

http://www.chemicalbook.com/Search_EN.aspx?keyword=2%2c4%2c6-TRIchloroANISOLE

http://en.wikipedia.org/wiki/Cork_taint

http://www.corktaint.com/

http://winesignofindia.wordpress.com/2012/02/21/cork-taint-in-wine-produced-by-246-trichloroanisole-tca/closure3/

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