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Hops
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===Thiols===
Sulfur-based compounds bound to a hydrogen atom known as ''thiols'' have also been shown to be produced by yeast fermentation from the hop derived precursors cysteine or glutathione via yeast β-lyase activity. This β-lyase activity is expressed by strains of ''Saccharomyces cerevisiae'' that have the ''IRC7'' gene. This activity takes place within the yeast cells which uptake the bound thiol precursorsand then expel the free thiols. Most industrial brewing and wine strains of ''S. cerevisiae'' do not have a functional version of this gene due to a lack of selective pressure. Even in strains with a functional version of the ''IRC7'' gene, the expression of the gene is repressed in nitrogen rich substrates such as wort <ref>[https://www.masterbrewerspodcast.com/227 Dr. Laura Burns and Lance Shaner. MBAA Podcast Episode 227 Interview. 10/18/2021. Retrieved 02/10/2023.]</ref>(~4 mins in). The cysteine and glutathione precursors are also found in malt, hops, grapes and rice, with levels varying greatly depending on varieties of the plants. In addition to some strains of ''Saccharomyces cerevisiae'' that express the genes to produce thiols, strains of the yeasts ''Metschnikowia pulcherrima'', ''Torulaspora delbrueckii'', ''Lachancea thermotolerans'', ''Candida zemplinina'', and the bacteria ''Lactobacillus plantarum'' have also been found to produce thiols <ref name="Svedlund_2022" />. So far, science has found that these include the volatile thiols:
* 3-mercaptohexan-1-ol (3MH; also referred to as 3-sulfanylhexan-1-ol, 3SH; ''tropical fruit'')
* 4-mercapto-4-methylpentan-2-one (4MMP; also referred to as 4-methyl-4-sulfanylpentan-2-one, 4MSP; ''blackcurrant'')
* 3-sulfanyl-4-methylpentyl acetate (3S4MPA; ''passionfruit'', ''grapefruit'')
* 3-mercaptohexyl acetate (3MHA; ''passionfruit'')
Typically, in beer and wine, the amount of free thiols that are formed from these precursors is less than 1%, perhaps due to poor activity of β-lyase activity in acidic media and inhibition by polyphenols. However, these thiols were found in beers dry hopped separately with Amarillo, Hallertau Blanc, and Mosaic hop varieties. The amounts of these two thiols were higher than expected based on the content of these thiols in the hops alone <ref name="Cibaka_2016" />. Dry hopping temperature plays a role, with with 18-24°C being optimum for 3Mh and 3MP, and 28°C being optimum for 3S4MP. Mash hopping can potentially increase thiols, while using copper in the brewing or winemaking process can reduce them <ref name="Svedlund_2022" />. In order to get around the nitrogen caused suppression of the IRC7 gene in brewing yeast, [[Omega Yeast Labs]] has bioengineered a yeast strain called [https://omegayeast.com/news/cosmic-punch-new-thiol-boosting-strain Cosmic Punch™ (British V OYL-011)] to produce significant amounts of thiols from hops and malted grains. [https://berkeleyyeast.com/available-yeast-strains/ Berkeley Yeast] also offers bioengineered yeast strains that produce thiols. See also this [https://www.facebook.com/groups/MilkTheFunk/permalink/1373899592638251/ MTF thread speculating on how ''Brettanomyces'' might produce thiols].
See also: