Difference between revisions of "Butyric Acid"
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| − | '''Butyric Acid''' (chemical name ''butyrate'' <ref>[https://en.wikipedia.org/wiki/Butyrate Butyrate. Wikipedia. Retrieved 6/20/2015.]</ref>) is a carboxylic acid that is produced by anaerobic bacteria such as ''Clostridium butyricum'', ''C. kluyveri'', and ''Megasphaera spp'' <ref name="wikipedia">[http://en.wikipedia.org/wiki/Butyric_acid#Production Wikipedia description of Butyric Acid production]</ref> during glucose fermentation, and is generally considered an off flavor in sour beer. If not done right, [[Sour Mashing]] can be a big producer of | + | '''Butyric Acid''' (chemical name '''butyrate''' <ref>[https://en.wikipedia.org/wiki/Butyrate Butyrate. Wikipedia. Retrieved 6/20/2015.]</ref>) is a carboxylic acid that is produced by anaerobic bacteria such as ''Clostridium butyricum'', ''C. kluyveri'', and ''Megasphaera spp'' <ref name="wikipedia">[http://en.wikipedia.org/wiki/Butyric_acid#Production Wikipedia description of Butyric Acid production]</ref> during glucose fermentation, and is generally considered an off flavor in sour beer. If not done right, [[Sour Mashing]] can be a big producer of butyric acid. Butyric acid is produced by anaerobic bacteria. The aroma and flavor is often described as a vomit, bile, or rancid cheese. It is also present in the human gut, and is the cause of the aroma of vomit <ref name="wikipedia"></ref>. This is not to be confused with [[Isovaleric Acid]] which has a more "feety" aroma and flavor. [[Brettanomyces]] can convert butyric acid into [[Ethyl Butyrate]] at low levels, which has a pineapple, tropical fruit aroma and flavor <ref>[http://www.brettanomycesproject.com/dissertation/pure-culture-fermentation/pure-culture-fermentation-discussion/ Chad Yakobson's Brettanomyces Dissertation]</ref>. Butyric acid has shown to have some health benefits in medical research <ref>[http://jmm.sgmjournals.org/content/59/2/141.full Van Immerseel F, Ducatelle R, De Vos M, Boon N, Van De Wiele T, Verbeke K, Rutgeerts P, Sas B, Louis P, Flint HJ. Butyric acid-producing anaerobic bacteria as a novel probiotic treatment approach for inflammatory bowel disease. J Med Microbiol 2010;59:141–3.]</ref>. |
==Microbes and Metabolism== | ==Microbes and Metabolism== | ||
===Clostridium spp=== | ===Clostridium spp=== | ||
| − | ''Clostridium'' is a Gram-positive anaerobic genus of bacteria that is found in plants, wounds, soil, and feces. It has also been found in spent grains. Several species of the genus ''Clostridium'' produce | + | ''Clostridium'' is a Gram-positive anaerobic genus of bacteria that is found in plants, wounds, soil, and feces. It has also been found in spent grains. Several species of the genus ''Clostridium'' produce butyric acid, and is produced in at least 3 days. ''Clostridium'' are generally anaerobic, but some can be active in aerobic conditions (aerotolerant), such as ''T. tertium''. Species of ''Clostridium'' that can produce butyric acid from glucose include ''C. butyricum'', ''C. fallax'', ''C. paraputrificum'', ''C. sartagoformum'', ''C. tertium'', ''C. thermosaccharolyticum'', and to a lesser degree ''C. pasteurianum''. <ref name="Hawthorne">[http://www.asbcnet.org/publications/journal/vol/abstracts/49-02.htm Butyric Acid Off-Flavors in Beer: Origins and Control. D. B. Hawthorne, R. D. Shaw, D. F. Davine, T. E. Kavanagh, and B. J. Clarke. 1991.]</ref> |
| − | ''Clostridium'' contamination in brewing methods such as [[Sour Mashing]] can be controlled by [[Sour_Worting#How_to_Pre-Acidify|lowering the pH of the wort/mash]]. However, some species of Clostridium are acid tolerant. For example, ''C. butyricum'' and ''C. tertium'' were found to survive a pH as low as 4.0 <ref>[http://www.hindawi.com/journals/isrn/2013/731430/ Growth Limiting pH, Water Activity, and Temperature for Neurotoxigenic Strains of Clostridium butyricum. Hamid B. Ghoddusi, Richard E. Sherburn, and Olusimbo O. Aboaba. 2013.]</ref><ref name="Hawthorne"></ref>. Therefore, pre-acidifying during the [[Sour Mashing]] process to a pH of 3.9 or lower may produce the best results (brewers have long reported good results with acidifying their wort/mash to a pH of 4.4; this may be a function of greatly suppressing | + | ''Clostridium'' contamination in brewing methods such as [[Sour Mashing]] can be controlled by [[Sour_Worting#How_to_Pre-Acidify|lowering the pH of the wort/mash]]. However, some species of ''Clostridium'' are acid tolerant. For example, ''C. butyricum'' and ''C. tertium'' were found to survive a pH as low as 4.0 <ref>[http://www.hindawi.com/journals/isrn/2013/731430/ Growth Limiting pH, Water Activity, and Temperature for Neurotoxigenic Strains of Clostridium butyricum. Hamid B. Ghoddusi, Richard E. Sherburn, and Olusimbo O. Aboaba. 2013.]</ref><ref name="Hawthorne"></ref>. Therefore, pre-acidifying during the [[Sour Mashing]] process to a pH of 3.9 or lower may produce the best results (brewers have long reported good results with acidifying their wort/mash to a pH of 4.4; this may be a function of greatly suppressing butyric acid bacteria, rather than eliminating it completely <ref>[https://www.facebook.com/groups/MilkTheFunk/permalink/1097057266989153/?comment_id=1097064400321773&offset=0&total_comments=6&comment_tracking=%7B%22tn%22%3A%22R2%22%7D Conversation with Derek Springer and Malcom Frazer on MTF. 6/22/2015.]</ref>). Fermentation by yeast also inhibits growth, probably due to out-competing the bacteria <ref name="Hawthorne"></ref>. |
Temperature resistance varies from species to species of ''Clostridium''. Most species have an optimal growth at around 104°F (37°C) <ref>[https://books.google.com/books?id=bA9tAwAAQBAJ&pg=PA232&lpg=PA232&dq=clostridium+butyricum++temperature+range&source=bl&ots=JQLbTobiNS&sig=qfc-2rsj3zOXHf4pGpvP6PW1A90&hl=en&sa=X&ei=-weGVbW-E8WeNtK4gfgP&ved=0CCQQ6AEwATgU#v=onepage&q=clostridium%20butyricum%20%20temperature%20range&f=false Textbook of Microbiology & Immunology. Subhash Chandra Parija. 2nd Edition. Feb 10, 2014.]</ref>. However, ''C. thermosaccharolyticum'' can survive temperatures as hot as 149°F (65°C). Additionally, spores of some species of ''Clostridium'' (such as ''C. tertium'') can survive boiling temperatures for longer than 1.5 hours <ref name="Hawthorne"></ref>. | Temperature resistance varies from species to species of ''Clostridium''. Most species have an optimal growth at around 104°F (37°C) <ref>[https://books.google.com/books?id=bA9tAwAAQBAJ&pg=PA232&lpg=PA232&dq=clostridium+butyricum++temperature+range&source=bl&ots=JQLbTobiNS&sig=qfc-2rsj3zOXHf4pGpvP6PW1A90&hl=en&sa=X&ei=-weGVbW-E8WeNtK4gfgP&ved=0CCQQ6AEwATgU#v=onepage&q=clostridium%20butyricum%20%20temperature%20range&f=false Textbook of Microbiology & Immunology. Subhash Chandra Parija. 2nd Edition. Feb 10, 2014.]</ref>. However, ''C. thermosaccharolyticum'' can survive temperatures as hot as 149°F (65°C). Additionally, spores of some species of ''Clostridium'' (such as ''C. tertium'') can survive boiling temperatures for longer than 1.5 hours <ref name="Hawthorne"></ref>. | ||
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===Megasphaera spp=== | ===Megasphaera spp=== | ||
| − | ''Megasphaera'' species produce large amounts of | + | ''Megasphaera'' species produce large amounts of butyric acid, as well as some acetic, isovaleric, valeric, and caproic acids. They are considered a true beer spoilage organism in beer. ''M. cerevisiae'' is a common species found in spoiled beer, and is a Gram-negative bacteria. They are obligate anaerobes, and die in the presence of oxygen. Growth occurs at a temperature range between 59°-98.6°F (15°-37°C), with an optimal growth rate at 82.4°F (28°C) <ref>[https://books.google.com/books?id=6JHxBwAAQBAJ&pg=PA238&lpg=PA238&dq=butyric+acid+bacteria+beer&source=bl&ots=knKFqJFgmA&sig=VmO6rhgzmwlqt_WXAlgm8I4Zgmg&hl=en&sa=X&ei=O8-FVcGQOYeggwTt9oPgAg&ved=0CDcQ6AEwAw#v=onepage&q=butyric%20acid%20bacteria%20beer&f=false Brewing Microbiology. Fergus Priest, Iain Campbell. Springer Science & Business Media, Jun 27, 2011.]</ref>. Growth of ''M. cerevisiae'' cannot occur above 5.3% abv, and slows significantly at 2.66% abv. Growth also stops at a pH of 4.0 or less <ref>[https://books.google.com/books?id=O0idBAAAQBAJ&pg=PA211&dq=Megasphaera+cerevisiae+ph&hl=en&sa=X&ei=CReGVf63PIunNt-Zo7gN&ved=0CB0Q6AEwAA#v=onepage&q=Megasphaera%20cerevisiae%20ph&f=false Brewing Microbiology: Managing Microbes, Ensuring Quality and Valorising Waste. Hill, Annie. Woodhead Publishing, May 26, 2015.]</ref>. |
===Fusobacterium nucleatum=== | ===Fusobacterium nucleatum=== | ||
| − | ''F. nucleatum'' is a Gram-netagive bacteria that is commonly found in dental plaque. It is capable of fermenting glucose into | + | ''F. nucleatum'' is a Gram-netagive bacteria that is commonly found in dental plaque. It is capable of fermenting glucose into butyric acid, and is tolerant of up to 6% oxygen <ref>[https://microbewiki.kenyon.edu/index.php/Fusobacterium_nucleatum Fusobacterium nucleatum. MicrobeWiki. Retrieved 6/21/2015.]</ref>. It has a optimal growth temperature at 98.6°F <ref>[https://www.atcc.org/~/ps/25586.ashx ATCC. Fusobacterium nucleatum subsp. nucleatum (ATCC ® 25586™). Retrieved 6/21/2015.]</ref>. ''F. nucleatum'' is sensitive to a pH of 5.0 and lower, and temperatures above 140°F (60°C) <ref>[http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2672.2009.04250.x/full Ribeiro-Ribas, R.N., De Carvalho, M.A.R., Vieira, C.A., Apolônio, A.C.M., Magalhães, P.P., Mendes, E.N., Oliveira, J.S., Santoro, M.M. and De Macêdo Farias, L. (2009), Purification and partial characterization of a bacteriocin produced by an oral Fusobacterium nucleatum isolate. Journal of Applied Microbiology, 107: 699–705. doi: 10.1111/j.1365-2672.2009.04250.x]</ref>. Avoid contaminating wort with saliva, and this organism shouldn't be a problem. |
===Other Microbes=== | ===Other Microbes=== | ||
| − | Other microbes that are | + | Other microbes that are butyric acid producers, probably won't be found in the brewhouse. These include bacteria that are commonly found in the guts of animals such as ''Butyrivibrio fibrisolvens'' <ref>[http://www.ncbi.nlm.nih.gov/pmc/articles/PMC203391/ Cotta, M A, and R B Hespell. “Proteolytic Activity of the Ruminal Bacterium Butyrivibrio Fibrisolvens.” Applied and Environmental Microbiology 52.1 (1986): 51–58. Print.]</ref> and ''Eubacterium limosum'' <ref>[http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3372111/ Lee, Meng-Rui et al. “Clinical and Microbiological Characteristics of Bacteremia Caused by Eggerthella, Paraeggerthella, and Eubacterium Species at a University Hospital in Taiwan from 2001 to 2010.” Journal of Clinical Microbiology 50.6 (2012): 2053–2055. PMC. Web. 22 June 2015.]</ref>. |
===Metabolism=== | ===Metabolism=== | ||
[[File:Butyrate pathway.jpeg|thumb|100px|Butyric acid pathway <ref name="Effects on Food Properties">[https://books.google.com/books?id=6SLB1j0rX78C&pg=PA76&lpg=PA76&dq=what+is+obligatory+facultatively+heterofermentative&source=bl&ots=6E4DB8Px_X&sig=PXZTNO4fB3ifCF_qAl5_I4euKmk&hl=en&sa=X&ei=Z-10VZqvFIWyggTInIHYBw&ved=0CCsQ6AEwAw#v=onepage&q=what%20is%20obligatory%20facultatively%20heterofermentative&f=false Fermentation: Effects on Food Properties. Bhavbhuti M. Mehta, Afaf Kamal-Eldin, Robert Z. Iwanski. CRC Press, Apr 12, 2012. Pg 76,77.]</ref>]] | [[File:Butyrate pathway.jpeg|thumb|100px|Butyric acid pathway <ref name="Effects on Food Properties">[https://books.google.com/books?id=6SLB1j0rX78C&pg=PA76&lpg=PA76&dq=what+is+obligatory+facultatively+heterofermentative&source=bl&ots=6E4DB8Px_X&sig=PXZTNO4fB3ifCF_qAl5_I4euKmk&hl=en&sa=X&ei=Z-10VZqvFIWyggTInIHYBw&ved=0CCsQ6AEwAw#v=onepage&q=what%20is%20obligatory%20facultatively%20heterofermentative&f=false Fermentation: Effects on Food Properties. Bhavbhuti M. Mehta, Afaf Kamal-Eldin, Robert Z. Iwanski. CRC Press, Apr 12, 2012. Pg 76,77.]</ref>]] | ||
| − | ''Clostridium'' species such as ''C. butyicum'', ''C. lactoacetophilum'', ''C. pasteurianum'', etc. produce | + | ''Clostridium'' species such as ''C. butyicum'', ''C. lactoacetophilum'', ''C. pasteurianum'', etc. produce butyric acid and acetic acid via the butyric acid fermentation pathway. Some species of ''Clostridium'', such as ''C. acetobutylicum'' also produce isopropanol or acetone. Carbon dioxide and ethanol are also produced during butyric acid fermentation, as well as butunol. <ref>[https://books.google.com/books?id=GjRwl1D0tiYC&pg=PA533&lpg=PA533&dq=butyric+acid+pathway&source=bl&ots=e68dMW_N1T&sig=C4v9NYkpuFC9Tq1AADTgJ71EJpw&hl=en&sa=X&ei=tI2HVYW1BLWQsQSngr_ICw&ved=0CG8Q6AEwDg#v=onepage&q=butyric%20acid%20pathway&f=false Principles of Microbiology. R S. Mehrotra. ata McGraw-Hill Education, 2009. Pg 53.]</ref>. ''Butanol'' is a solventy smelling alcohol <ref>[http://pubchem.ncbi.nlm.nih.gov/compound/1-butanol#section=Top PubMed. 1-Butanol. Retrieved 6/21/2015.]</ref>. |
==See Also== | ==See Also== | ||
Revision as of 11:44, 29 September 2015
Butyric Acid (chemical name butyrate [1]) is a carboxylic acid that is produced by anaerobic bacteria such as Clostridium butyricum, C. kluyveri, and Megasphaera spp [2] during glucose fermentation, and is generally considered an off flavor in sour beer. If not done right, Sour Mashing can be a big producer of butyric acid. Butyric acid is produced by anaerobic bacteria. The aroma and flavor is often described as a vomit, bile, or rancid cheese. It is also present in the human gut, and is the cause of the aroma of vomit [2]. This is not to be confused with Isovaleric Acid which has a more "feety" aroma and flavor. Brettanomyces can convert butyric acid into Ethyl Butyrate at low levels, which has a pineapple, tropical fruit aroma and flavor [3]. Butyric acid has shown to have some health benefits in medical research [4].
Contents
Microbes and Metabolism
Clostridium spp
Clostridium is a Gram-positive anaerobic genus of bacteria that is found in plants, wounds, soil, and feces. It has also been found in spent grains. Several species of the genus Clostridium produce butyric acid, and is produced in at least 3 days. Clostridium are generally anaerobic, but some can be active in aerobic conditions (aerotolerant), such as T. tertium. Species of Clostridium that can produce butyric acid from glucose include C. butyricum, C. fallax, C. paraputrificum, C. sartagoformum, C. tertium, C. thermosaccharolyticum, and to a lesser degree C. pasteurianum. [5]
Clostridium contamination in brewing methods such as Sour Mashing can be controlled by lowering the pH of the wort/mash. However, some species of Clostridium are acid tolerant. For example, C. butyricum and C. tertium were found to survive a pH as low as 4.0 [6][5]. Therefore, pre-acidifying during the Sour Mashing process to a pH of 3.9 or lower may produce the best results (brewers have long reported good results with acidifying their wort/mash to a pH of 4.4; this may be a function of greatly suppressing butyric acid bacteria, rather than eliminating it completely [7]). Fermentation by yeast also inhibits growth, probably due to out-competing the bacteria [5].
Temperature resistance varies from species to species of Clostridium. Most species have an optimal growth at around 104°F (37°C) [8]. However, C. thermosaccharolyticum can survive temperatures as hot as 149°F (65°C). Additionally, spores of some species of Clostridium (such as C. tertium) can survive boiling temperatures for longer than 1.5 hours [5].
Although C. botulinum and other identifiably pathogenic Clostridium species do not tend to grow in Sour Mashing conditions, it is advisable to not consume wort produced from a sour mash until after it is boiled. Seek specific food and safety advice from a qualified physician, not this wiki.
Megasphaera spp
Megasphaera species produce large amounts of butyric acid, as well as some acetic, isovaleric, valeric, and caproic acids. They are considered a true beer spoilage organism in beer. M. cerevisiae is a common species found in spoiled beer, and is a Gram-negative bacteria. They are obligate anaerobes, and die in the presence of oxygen. Growth occurs at a temperature range between 59°-98.6°F (15°-37°C), with an optimal growth rate at 82.4°F (28°C) [9]. Growth of M. cerevisiae cannot occur above 5.3% abv, and slows significantly at 2.66% abv. Growth also stops at a pH of 4.0 or less [10].
Fusobacterium nucleatum
F. nucleatum is a Gram-netagive bacteria that is commonly found in dental plaque. It is capable of fermenting glucose into butyric acid, and is tolerant of up to 6% oxygen [11]. It has a optimal growth temperature at 98.6°F [12]. F. nucleatum is sensitive to a pH of 5.0 and lower, and temperatures above 140°F (60°C) [13]. Avoid contaminating wort with saliva, and this organism shouldn't be a problem.
Other Microbes
Other microbes that are butyric acid producers, probably won't be found in the brewhouse. These include bacteria that are commonly found in the guts of animals such as Butyrivibrio fibrisolvens [14] and Eubacterium limosum [15].
Metabolism
Butyric acid pathway [16]
Clostridium species such as C. butyicum, C. lactoacetophilum, C. pasteurianum, etc. produce butyric acid and acetic acid via the butyric acid fermentation pathway. Some species of Clostridium, such as C. acetobutylicum also produce isopropanol or acetone. Carbon dioxide and ethanol are also produced during butyric acid fermentation, as well as butunol. [17]. Butanol is a solventy smelling alcohol [18].
See Also
Additional Articles on MTF Wiki
External Resources
References
- ↑ Butyrate. Wikipedia. Retrieved 6/20/2015.
- ↑ 2.0 2.1 Wikipedia description of Butyric Acid production
- ↑ Chad Yakobson's Brettanomyces Dissertation
- ↑ Van Immerseel F, Ducatelle R, De Vos M, Boon N, Van De Wiele T, Verbeke K, Rutgeerts P, Sas B, Louis P, Flint HJ. Butyric acid-producing anaerobic bacteria as a novel probiotic treatment approach for inflammatory bowel disease. J Med Microbiol 2010;59:141–3.
- ↑ 5.0 5.1 5.2 5.3 Butyric Acid Off-Flavors in Beer: Origins and Control. D. B. Hawthorne, R. D. Shaw, D. F. Davine, T. E. Kavanagh, and B. J. Clarke. 1991.
- ↑ Growth Limiting pH, Water Activity, and Temperature for Neurotoxigenic Strains of Clostridium butyricum. Hamid B. Ghoddusi, Richard E. Sherburn, and Olusimbo O. Aboaba. 2013.
- ↑ Conversation with Derek Springer and Malcom Frazer on MTF. 6/22/2015.
- ↑ Textbook of Microbiology & Immunology. Subhash Chandra Parija. 2nd Edition. Feb 10, 2014.
- ↑ Brewing Microbiology. Fergus Priest, Iain Campbell. Springer Science & Business Media, Jun 27, 2011.
- ↑ Brewing Microbiology: Managing Microbes, Ensuring Quality and Valorising Waste. Hill, Annie. Woodhead Publishing, May 26, 2015.
- ↑ Fusobacterium nucleatum. MicrobeWiki. Retrieved 6/21/2015.
- ↑ ATCC. Fusobacterium nucleatum subsp. nucleatum (ATCC ® 25586™). Retrieved 6/21/2015.
- ↑ Ribeiro-Ribas, R.N., De Carvalho, M.A.R., Vieira, C.A., Apolônio, A.C.M., Magalhães, P.P., Mendes, E.N., Oliveira, J.S., Santoro, M.M. and De Macêdo Farias, L. (2009), Purification and partial characterization of a bacteriocin produced by an oral Fusobacterium nucleatum isolate. Journal of Applied Microbiology, 107: 699–705. doi: 10.1111/j.1365-2672.2009.04250.x
- ↑ Cotta, M A, and R B Hespell. “Proteolytic Activity of the Ruminal Bacterium Butyrivibrio Fibrisolvens.” Applied and Environmental Microbiology 52.1 (1986): 51–58. Print.
- ↑ Lee, Meng-Rui et al. “Clinical and Microbiological Characteristics of Bacteremia Caused by Eggerthella, Paraeggerthella, and Eubacterium Species at a University Hospital in Taiwan from 2001 to 2010.” Journal of Clinical Microbiology 50.6 (2012): 2053–2055. PMC. Web. 22 June 2015.
- ↑ Fermentation: Effects on Food Properties. Bhavbhuti M. Mehta, Afaf Kamal-Eldin, Robert Z. Iwanski. CRC Press, Apr 12, 2012. Pg 76,77.
- ↑ Principles of Microbiology. R S. Mehrotra. ata McGraw-Hill Education, 2009. Pg 53.
- ↑ PubMed. 1-Butanol. Retrieved 6/21/2015.