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Dimethyl Sulfide

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'''Dimethyl sulfide (or DMSfor short)''', sometimes spelled "dimethyl sulphide" <ref name="pubchem"></ref>, is the simplest type of [https://en.wikipedia.org/wiki/Thioether thioether] <ref name="Scheuren2016">[http://onlinelibrary.wiley.com/doi/10.1002/jib.301/full Evaporation behaviour of DMS in an aqueous solution at infinite dilution – a review. H. Scheuren, M. Baldus, F.-J. Methner and M. Dillenburger. 2016]</ref>, which are sulfur-containing oils that are generally considered off-putting in beer <ref>[https://en.wikipedia.org/wiki/Thioether Wikipedia. Thioether. Retrieved 03/01/2016.]</ref><ref name="Anness">[http://onlinelibrary.wiley.com/doi/10.1002/j.2050-0416.1982.tb04101.x/abstract DIMETHYL SULPHIDE—A REVIEW. B. J. Anness and C. W. Bamforth. 1982.]</ref>. The flavor and aroma of DMS have been characterized as being like cooked sweetcorn, tomato sauce, celery, or sauerkraut. In beer, it is sometimes confused with methyl thiocetate, ethanethiol, and dimethyl trisulphide. DMS in beer originates from the malt-derived precursors, S-methyl methionine (SMM) and dimethyl sulphoxide (DMSO). SMM is converted to DMS during boiling wort, and to a lesser extent DMS can be formed from DMSO during fermentation by certain microbes <ref name="aroxa">[http://www.aroxa.com/beer/beer-flavour-standard/dimethyl-sulphide/ Aroxa. Dimethyl sulphide. Retrieved 03/01/2016.]</ref>. Small amounts of DMS have also been found in hops, which is volatilized during boiling <ref name="Scheuren2014">[http://onlinelibrary.wiley.com/doi/10.1002/jib.156/abstract Decomposition kinetics of dimethyl sulfide. H. Scheuren, J. Tippmann, F.-J. Methner, and, K. Sommer. 2014.]</ref>. The flavor threshold of DMS is 30-50 µg/liter. Low levels above threshold between 30-100 µg/liter are considered acceptable and even beneficial to some lagers in the United Kingdom (but not in Germany) <ref name="beersmith"></ref> (~25 minutes in), and maybe some traditional farmhouse ales that are not boiled (see [[Dimethyl_Sulfide#Considerations_for_Historical_Examples_of_Raw_Ale|Considerations for Historical Examples of Raw Ale]]). However, amounts above 100 µg/liter are generally considered offensive for any beer. Ales typically have below the flavor threshold of DMS <ref name="Anness"></ref>. The basis of the understanding of DMS and it's creation in beer was uncovered in the late 70's and early 80's. DMS is a common compound found throughout nature, including having an importance in cycling sulfur in ecosystems involving algae and other microbes, helping the navigation of seabirds, and is found in many foods such as corn, cabbage, parsley, asparagus, potatoes, beef, Camembert cheese, fish (carp), tea, cocoa, milk, wine, rum, beetroot, black truffles, and seafood <ref name="Scheuren2016"></ref><ref name="bamforth">[http://www.asbcnet.org/publications/journal/vol/abstracts/ASBCJ-2014-0610-01.htm Dimethyl Sulfide – Significance, Origins, and Control. Charles W. Bamforth. 2014.]</ref>. DMS can be [https://beersensoryscience.wordpress.com/2011/06/02/corn/ confused with a malt-based compound called 2-acetylpyridine (2AP)] which is formed during Maillard reactions and is described as tasting like "corn tortilla"; 2AP has also been confused with [[Tetrahydropyridine#Similar_Compounds|tetrahydropyridines]].
==Production From Malt==
* [http://onlinelibrary.wiley.com/doi/10.1002/jib.156/abstract Scheuren, Tippmann, Methner, Sommer (2014): calculation for wort boiled below atmospheric pressure.]
* [http://onlinelibrary.wiley.com/doi/10.1002/jib.234/abstract Scheuren, Sommer, and Dillenburger (2015): calculating DMS formation during mashing due to DMS volatility and thermodynamics.]
 
====Mark Price DMS Online Calculator====
[https://pricelessbrewing.github.io/BiabCalc/DMS2 Click here] for an online calculator that uses the updated prediction model above to predict DMS; calculator created by Mark Price.
==See Also==
===External Resources===
* [https://beersmith.com/blog/2024/01/23/dms-in-beer-with-dr-charlie-bamforth-beersmith-podcast-296/ "DMS in beer" by BeerSmith podcast; interview Dr. Charlie Bamforth for a deep dive into the chemistry of DMS.]
* [https://www.facebook.com/groups/MilkTheFunk/permalink/1367101639984713/ MTF Poll and Discussion on perceived DMS in different approaches to boiling/not boiling.]
* [http://scottjanish.com/how-to-prevent-dms-in-beer/ "How To Prevent DMS In Beer," by Scott Janish.]

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