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Tetrahydropyridine

No change in size, 13:28, 17 September 2015
updated aging out timeframe
Forms of '''Tetrahydropyridines''' (THP), specifically 6-Acetyl-2,3,4,5-tetrahydropyridine (ATHP or ACTPY), 2-ethyltetrahydropyridine (ETHP), and 2-acetyl-1-pyrroline (ACPY or APY) <ref name="wikipedia">[http://en.wikipedia.org/wiki/6-Acetyl-2,3,4,5-tetrahydropyridine 6-Acetyl-2,3,4,5-tetrahydropyridine. Wikipedia. Retrieved 3/210/2015.]</ref>, which are classified as ketones <ref>[https://www.facebook.com/groups/MilkTheFunk/permalink/1034461653248715/?comment_id=1034611563233724&offset=0&total_comments=29 Humbard, Matt. Milk The funk Discussion. 3/10/2015.]</ref>, are commonly attributed to the "mousy", "urine" (in high amounts) "cheerios" or "Captain Crunch" (in low amounts), "breakfast cereal", or more generically, "cracker biscuit" flavor in sour beers. The flavor is detected towards the end of the swallow. Diacetyl is sometimes mistakenly indicated as a potential cause of this flavor in sour beers. However, Tetrahydropyridines are the accepted cause. The flavor tends to age out of sour beers after 2-3 6 months (it is unknown whether cold or room temperature storage speeds this up), although the exact mechanism for this is not fully understood <ref>[http://www.homebrewtalk.com/f127/cheerios-character-after-bottling-504468/#post6516169 Tonsmeire, Michael. Homebrewtalk.com post 1. 11/21/2014. Retrieved 3/10/2015.]</ref>. Many brewers have noticed that pitching rehydrated wine yeast at bottling reduces the amount/duration of this flavor <ref>[http://www.homebrewtalk.com/f127/cheerios-character-after-bottling-504468/#post6522207 Tonsmeire, Michael. Homebrewtalk.com post 2. 11/21/2014. Retrieved 3/10/2015.]</ref>.
In food, Tetrahydropyridines are associated with the aroma of baked goods such as white bread, popcorn, and tortillas, and is formed by Maillard reactions during heating. ATHP and APY have an odor threshold of 0.06ng/l <ref name="wikipedia"></ref>.
ATHP is further metabolized into 2-ethyltetrahydropyridine (ETHP/ETPY) by Brettanomyces, although not much is known about this metabolic process <ref>[http://ucce.ucdavis.edu/files/repositoryfiles/Joseph_5_Aromatic_Diverswity_of_Brettanomyces-82350.ppt Joseph, C.M. Lucy. ''Aromatic Diversity of Brettanomyces''. U.C. Davis. Retrieved 3/10/2015.]</ref>. ETHP has a significantly higher taste threshold, and is often not detected in contaminated wine <ref name="Oelofse"></ref>.
The presence of the "mousy off-flavor" caused by THP appears to be temporary in beer. Although not much is known about the degradation or metabolic break down of ATHP/ETHP, it tends to age out of beer after 2-3 6 months. Another unknown is why ''Brett'' produces THP shortly after kegging and force carbonating a beer that has reached final gravity. Pitching fresh ''Saccharomyces'' for bottle conditioning a beer with ''Brett'' in it has reportedly reduced THP production, perhaps through the quicker metabolism of both the oxygen and sugar that is introduced during packaging time.
Heterofermentative [[Lactobacillus]] spp., particularly ''L. hilgardii'' and ''L. brevis'', can also produce ATHP and ETHP from Lysine and ethanol <ref name="Costello">[http://pubs.acs.org/doi/abs/10.1021/jf020341r Mousy Off-Flavor of Wine:  Precursors and Biosynthesis of the Causative N-Heterocycles 2-Ethyltetrahydropyridine, 2-Acetyltetrahydropyridine, and 2-Acetyl-1-pyrroline by Lactobacillus hilgardii DSM 20176. Peter J. Costello and Paul A. Henschke. 2002.]</ref><ref>[http://www.ajevonline.org/content/37/2/127.abstract Formation of Substituted Tetrahydropyridines by Species of Brettanomyces and Lactobacillus Isolated from Mousy Wines. Tamila Heresztyn. 1986.]</ref><ref>[http://onlinelibrary.wiley.com/doi/10.1111/j.1755-0238.2001.tb00205.x/abstract Ability of lactic acid bacteria to produce N-heterocycles causing mousy off-flavour in wine. PETER J. COSTELLO1, TERRY H. LEE1, and PAULA. HENSCHKE. 2008.]</ref><ref>Sparrows, Jeff. ''Wild Brews''. Brewers Publications. 2005. Pg. 112.</ref><ref>[https://books.google.com/books?id=tFjsAuo5WocC&pg=PA348&lpg=PA348&dq=lactobacillus+Tetrahydropyridine&source=bl&ots=QUVyoFtIwK&sig=h1cdjB0r1pIRX2Bms8wVA0UiLk4&hl=en&sa=X&ei=4DX_VPz5CsH6oQSAzoGgBA&ved=0CEwQ6AEwCQ#v=onepage&q=lactobacillus%20Tetrahydropyridine&f=false Lahtinen, Ouwehand, Salminen, von Wright. Lactic Acid Bacteria: Microbiological and Functional Aspects, Fourth Edition. Pg 348.]</ref><ref>[http://ajevonline.org/content/37/2/127.short Heresztyn, Tamila. Formation of Substituted Tetrahydropyridines by Species of Brettanomyces and Lactobacillus Isolated from Mousy Wines.]</ref>. Most species of [[Pediococcus]] do not create THP, although a few species do. In particular, these include ''P. pentosaceus'' <ref>[http://www.uniprot.org/uniprot/Q03HT0 UniProt article. Retrieved 3/10/2015.]</ref><ref>[http://www.uniprot.org/uniprot/U5ZF76 UniProt article. Retrieved 3/10/2015.]</ref>, and ''P. clausenii'' <ref>[http://www.uniprot.org/uniprot/G8PEU4 UniProt article. Retrieved 3/10/2015.]</ref> (note that commercial cultures of [[Pediococcus]] are normally ''P. damnosus''). ''Oenococcus oeni'' and ''Leuconostoc mesenteroides'' have also been associated with creating THP <ref name="Costello"></ref>.

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