13,591
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Hops
,udates to biotransformation
Some carbonyl compounds found in hops (citral, geranial, nerol, [https://en.wikipedia.org/wiki/Citronellal citronellal], and methyl ketones) can be used as a food source by yeast during fermentation. ''Cyclic ethers'' such as linalool oxides, karahana ether, hop ether, and rose oxide (aroma of roses <ref>[http://www.thegoodscentscompany.com/data/rw1035651.html "(Z)-rose oxide ". Good Scents Company. Retrieved 12/29/2016.]</ref>), increase after fermentation and have been identified as secondary metabolites produced by yeast during metabolism from hop derived precursors. ''Esters'' found in hops can be converted into ethyl esters by yeast during fermentation; for example geranyl esters found in Cascade hops can be hydrolized into geraniol (flowery). The terpenoid [https://en.wikipedia.org/wiki/Citronellol citronellol] (citrus and floral <ref>[https://eic.rsc.org/magnificent-molecules/citronellol/2000020.article "There are no flies on Emma Stoye". Emma Stoye. Education in Chemistry website. 06/01/2016. Retrieved 01/10/2017.]</ref>) can be esterified by yeast fermentation into citronellyl acetate (fresh, rosy, fruity odor reminiscent of geranium oil <ref>[https://shop.perfumersapprentice.com/p-6034-citronellyl-acetate.aspx "Citronellyl acetate". Perfumers Apprentice website. Retrieved 01/10/2017.]</ref>). Yeast strains differ in their ability to convert these compounds. For example, one study found that lager yeast was able to form acetate esters of geraniol and citronellol, but ale yeast was not <ref name="Praet_2012" />.
Terpenes and terpenoids (monoterpene alcohols) can also be transformed by fermentation. Studies have found that geraniol and nerol can transform into linalool by a strain of ''S. cerevisiae'', as well as nerol and linalool to into alpha-terpineol, which can then by further transformed to terpin. Geraniol can also be converted into citronellol, and the content of geraniol and citronellol can be increased in finished beer by increasing the initial content of geraniol, which is found in higher quantities in some varieties of hops (Citra, for example). Linalool, nerol, and alpha-terpineol gradually decrease during fermentation and aging (perhaps being transformed into ethers), while nerol and citronellol gradually increase. Geraniol also decreases during fermentation, but not as drastically as linalool. Citronellol might It has been hyptothesized that the bioconversion of geraniol into ctironellol could be created from geraniol by means of glycosidic activity (although another study found that glycosidic activity in ''S. cerevisiae'' is not very strong). Likewise, postPost-fermentation dry hopping preserves linalool and alpha-terpineol, and limits citronellol to trace levels <ref name="Praet_2012" />. Takoi et al. (2012) used Citra hops with a high content of geraniol, and reported a steep decline on geraniol during the first three days of fermentation with a lager yeast. Linalool had a gradual decline, but ended up at higher levels than geraniol in the finished beer. Citronellol had a sharp increase during the first three days of fermentation, and then remained at a stable level until the end of fermentation. However, after storing the beer at 15°C (59°F) for 1 week, the amount of citronellol more than doubled. This indicated that active fermentation may not required for the transformation of geraniol into citronellol <ref>[https://onlinelibrary.wiley.com/doi/abs/10.1002 /j.2050-0416.2010.tb00428.x The Contribution of Geraniol Metabolism to the Citrus Flavour of Beer: Synergy of Geraniol and β‐Citronellol Under Coexistence with Excess Linalool. Kiyoshi Takoi, Yutaka Itoga, Koichiro Koie, Takayuki Kosugi, Masayuki Shimase, Yuta Katayama, Yasuyuki Nakayama, Junji Watari. 2012. DOI: https://doi.org/10.1002/j.2050-0416.2010.tb00428.x.]</ref>. Other yeast species can also convert monoterpenes. For example, a strain of ''Kluyveromyces lactis'' was found to reduce geraniol to citronellol. This strain and a strain of ''Torulaspora delbrueckii'' produced linalool from both geraniol and nerol, and could also form geraniol from nerol <ref>[https://www.ncbi.nlm.nih.gov/pubmed/10790686 Biotransformation of monoterpene alcohols by Saccharomyces cerevisiae, Torulaspora delbrueckii and Kluyveromyces lactis. King A1, Richard Dickinson J. 2000.]</ref>. Many species of ''Debaryomyces'', ''Kluyveromyces'', and ''Pichia'' were found to transform geraniol into linalool, and nerol into linalool and alpha-terpineol <ref>[https://www.ncbi.nlm.nih.gov/pubmed/18357555 Biotransformation of acyclic monoterpenoids by Debaryomyces sp., Kluyveromyces sp., and Pichia sp. strains of environmental origin. Ponzoni C, Gasparetti C, Goretti M, Turchetti B, Pagnoni UM, Cramarossa MR, Forti L, Buzzini P. 2008.]</ref>.
Sulfur based compounds known as ''thiols'' have also been shown to be produced by yeast fermentation from hop derived precursors (suspected to be S-glutathione). So far, science has found that these include the volatile thiols 3-sulfanyl-4-methylpentan-1-ol (3S4MP; grapefruit) and 3-sulfanyl-4-methylpentyl acetate (3S4MPA; passionfruit, grapefruit). 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" />.