Isolation and Identification of 2-Methoxy-3,5-dimethylpyrazine, a Potent Musty Compound from Wine Corks

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. Keywords: Cork taint; 2-methoxy-3,5-dimethylpyrazine; 2-hydroxy-3,5-dimethylpyrazine; 7-methyl-1,6-dioxaspiro[4.5]decane; mustiness; cork; wine