2-Methoxy-3,5-dimethylpyrazine

Aroma compound 2-Methoxy-3,5-dimethylpyrazine 2-Methoxy-3,5-dimethylpyrazine.svg 150px 2-Methoxy-3,5-dimethylpyrazine 3,5-dimethyl-2-methoxypyrazine 92508-08-2 6429218 4934595 193651 809-795-6 1S/C7H10N2O/c1-5-4-8-7(10-3)6(2)9-5/h4H,1-3H3 BXKLSVWRSUPMBO-UHFFFAOYSA-N CC1=CN=C(C(=N1)C)OC 7 10 2 1 Colorless to pale yellow liquid 2-Methoxy-3,5-dimethylpyrazine (sometimes abbreviated as MDMP) is a heterocyclic organic compound, part of methoxypyrazine class. It has a highly potent aroma with a strong musty, moldy, or earthy scent. It is best known as a source of cork taint in wine, secondary in importance to 2,4,6-trichloroanisole (TCA).Simpson Capone Sefton 2004 Natural occurrence 2-Methoxy-3,5-dimethylpyrazine has been identified as a natural product and a volatile organic compound responsible for off-odors in various products. It is a significant contributor to the "fungal must" or "corky" taint in wine, which is distinct from the smell caused by TCA.Simpson Capone Sefton 2004 The compound is not only found in cork stoppers but can also be present in oak wood used for barrel making.Chatonnet Cunha Rosenthal Pons 2010 Its presence has also been detected in coffee.Czerny Grosch 2000 868 The bacterium Rhizobium excellensis, which is widespread in the soil, is capable of producing 2-methoxy-3,5-dimethylpyrazine from amino acid precursors such as L-leucine and L-alanine.Chatonnet Cunha Rosenthal Pons 2010 The compound has also been identified as the cause of musty odors in public water supplies.Ventura Quintana Gómez Velo-Cid 2009 Aroma The aroma of 2-methoxy-3,5-dimethylpyrazine is variously described as musty, moldy, earthy, "like a potato bin", or reminiscent of wet cork and fresh hazelnuts.Chatonnet Cunha Rosenthal Pons 2010Simpson Capone Sefton 2004 It is an extremely potent odorant with a very low odor detection threshold. In white wine, its threshold has been determined to be as low as 2.1 nanograms per liter.Simpson Capone Sefton 2004 This potency means that even trace amounts of the compound can have a significant negative impact on the sensory profile of a wine or other beverage. Synthesis The synthesis is described in detail by Simpson et al.Simpson Capone Sefton 2004Chatonnet Cunha Rosenthal Pons 2010 12482 References Sources Chatonnet Pascal Cunha Jorge Rosenthal Didier Pons Monique Origin and Incidence of 2-Methoxy-3,5-dimethylpyrazine, a Compound with a "Fungal" and "Corky" Aroma Found in Cork Stoppers and Oak Chips in Contact with Wines Journal of Agricultural and Food Chemistry 8 December 2010 58 23 12481–12490 10.1021/jf102874f 21058737 2010JAFC...5812481C https://www.academia.edu/12147873 Czerny Michael Grosch Werner Potent Odorants of Raw Arabica Coffee. Their Changes during Roasting Journal of Agricultural and Food Chemistry 48 3 2000-03-01 0021-8561 10.1021/jf990609n 868–872 10725165 2000JAFC...48..868C Simpson Robert F. Capone Dimitra L. Sefton Mark A. Isolation and Identification of 2-Methoxy-3,5-dimethylpyrazine, a Potent Musty Compound from Wine Corks Journal of Agricultural and Food Chemistry 52 17 2004-08-01 0021-8561 10.1021/jf049484z 5425–5430 15315380 2004JAFC...52.5425S https://pubs.acs.org/doi/10.1021/jf049484z 2025-07-05 subscription Ventura Francesc Quintana Jordi Gómez Mariano Velo-Cid Mónica Identification of 2-methoxy-3,5-dimethylpyrazine as the obnoxious compound at trace levels in water supplies AWWA Water Quality Technology Conference 2009 American Water Works Association https://www.researchgate.net/publication/333403716 Category:Pyrazines Category:Wine chemistry Category:Methoxy compounds