Isovaleric Acid

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Isovaleric Acid, also known as 3-Methylbutanoic acid, is an organic compound with the formula (CH3)2CHCH2CO2H. The flavor and aroma are often described as rancid Parmesan, or foot odor. It is not to be confused with Butyric Acid, which specifically has a more bile or vomit aroma and flavor. The flavor threshold of isovaleric acid has been reported to be 1 mg/L [1] and 1.5 mg/L [2]. It has a boiling temperature of 347-351°F (175-177°C) [3].

Production in Beer and Wine

Brettanomyces can create isovaleric acid [3]. The compound generally takes a few months to produce in beer by Brettanomyces. Brettanomyces breaks down leucine present in beer into isovaleric acid (controversial, but generally accepted) [4][5].

Isovaleric acid can also be produced by a bacteria that lives naturally on human skin and is responsible for foot odor called Staphylococcus epidermidis. It does so by degrading leucine, an amino acid present in sweat [6]. Leucine is also present in beer [7].

It has been shown in Swiss-type cheese that other bacteria, including species and strains of Streptococcus (more so) Lactobacillus (less so) can produce various amounts of isovaleric acid from leucine, as well as other compounds from other carboxylic acids. Lactobacillus is not capable of producing isovaleric acid without the presence of an alpha-keto acid, which is produced by Streptococcus thermophilus, so the presence of S. thermophilus or another alpha-keto acid producing microorganism is required for Lactobacillus to produce isovaleric acid (as well as a range of other acids). [8]. This has not been shown to occur in beer, but this may be the reason that sour mashes often have a rancid cheese off flavor (although this may also be at least partially due to Butyric Acid production during Sour Mashing).

Isovaleric acid can also be produced by the oxidation of hops, and is often found in hops aged for traditional lambic brewing [9][10].

Kettle Souring

Professional brewer Khristopher Johnson has observed the taste of isovaleric acid in kettle soured beers. Purging with CO2 has been quoted as something that has resolved this issue, the hypothesis being that oxygen could promote the formation of isovaleric acid if aerobic contaminates are present [11].

One study compared the levels of isovaleric acid in a kettle soured beer (flushed with CO2), a sour mashed beer (flushed with CO2), and a beer co-fermented with Lactobacillus amylovorus and US-05. They found that there was a significant increase in isovaleric acid when the Lactobacillus and US-05 were co-fermented (see the table below). The authors suggested that this might be due to the release of the amino acid precursors by the Lactobacillus towards the end of its life cycle when it was allowed to survive in a co-fermentation, versus being killed in the kettle souring/mash souring batches [2].

Method Amount of IVA (mg/L) [2]
US-05 Only (control) 0.83
Mash Souring with L. amylovorus and primary fermentation with US-05 0.72
Kettle Souring L. amylovorus and primary fermentation with US-05 0.50
Co-fermentation with L. amylovorus and US-05 1.15

Other Producers

Other bacteria have been shown to create isovaleric acid, and may contribute to the production of it in beer in unsanitary conditions. Bacillus amyloliquefaciens and B. atrophaeus are Gram-positive, aerobic (require oxygen for growth) bacteria and have been shown to produce isovaleric acid [12][13][14]. Xanthobacter agilis is a Gram-negative aerobic bacteria that can produce isovaleric acid [12][15]. Paenibacillus macerans is a facultative anaerobe (can utilize oxygen if present, but oxygen is not required) that can produce isovaleric acid. P. macerans is a Gram-variable bacteria, meaning that it can produce Gram-positive and Gram-negative rods [16]. The strict anaerobe, Megasphaera cerevisiae, which has been identified as a beer spoiler, can also produce isovaleric acid (as well as butyric acid, valeric acid, caproic acid, and hyrodgen sulfide) [17].

Metabolic Breakdown

Brettanomyces can break down isovaleric acid into an ester called ethyl isovalerate. This ester is described as fruity, sweet, berry-like with a ripe, pulpy fruit nuance [18][19][20]. The rate of metabolic breakdown of isovaleric acid into ethyl isovalerate has not been researched, as far as the authors of this wiki know. See also Brettanomyces ester production.

References

  1. Aroxa. Isovaleric acid. Retreived 12/30/2015.
  2. 2.0 2.1 2.2 Sour Brewing: Impact of Lactobacillus amylovorus FST2.11 on Technological and Quality Attributes of Acid Beers. Lorenzo C. Peyer, Martin Zarnkow, Fritz Jacob, David P. Schutter, Elke K. Arendt. 2017.
  3. 3.0 3.1 Wikipedia article
  4. Botha, Janita J. Sensory, chemical and consumer analysis of Brettanomyces spoilage in South African wines. March 2010. Pg 2, 13, 17, 18
  5. Oelofse, Adriaan. Investigating the role of Brettanomyces and Dekkera during winemaking. December 2008.
  6. Ara K, Hama M, Akiba S, Koike K, Okisaka K, Hagura T, Kamiya T, Tomita F. Can J Microbiol. 2006 Apr.
  7. Hall, Nutfield, Redhill, Surrey. Amino Acid Esters in Beer. Brewing Research Foundation. July 14, 1980.
  8. Helinck, Le Bars, Moreau, and Yvon. Ability of thermophilic Lactic Acid Bacteria To Produce Aroma Compounds from Amino Acids.
  9. Green, C. P. The Volatile Water-Soluble Fraction Of Hop Oil. Aug 24, 1909.
  10. Oliver, Garret. The Oxford Companion to Beer. 2001. Pg 498.
  11. Khristopher Johnson. Milk The Funk Facebook group. 08/03/2017.
  12. 12.0 12.1 Phosphate-solubilizing microorganisms associated with the rhizosphere of mangroves in a semiarid coastal lagoon. P. Vazquez, G. Holguin, M.E. Puente, A. Lopez-Cortes, Y. Bashan. 2000.
  13. Bacillus amyloliquifaciens. Carl Sather's website. Retrieved 10/06/2015.
  14. Bacillus atrophaeus: main characteristics and biotechnological applications – a review. Sandra R B R Sella, Luciana Vandenberghe, Carlos Ricardo Soccol. 2014.
  15. Xanthobacter agilis. The Lab Rat. Retrieved 10/06/2015.
  16. Paenibacillus macerans. Wikipedia. Retrieved 10/06/2015.
  17. Monoclonal Antibodies Binding to Lipopolysaccharide from the Beer-Spoilage Bacterium Megasphaera cerevisiae Exhibit Panreactivity with the Strictly Anaerobic Gram-Negative Brewing-Related Bacteria. Barry Ziola. 2016.
  18. Fenaroli's Handbook of Flavor Ingredients, Fifth Edition. George A. Burdock. CRC Press, Dec 3, 2004. Pg 587.
  19. Supplemental Data for: Joseph, C.M.L., E.A. Albino, S.E. Ebeler, and L.F. Bisson. Brettanomyces bruxellensis aroma-active compounds determined by SPME GC-MS olfactory analysis. 2015.
  20. Impact of Brettanomyces on Wine. Presentation by Lucy Joseph of UC Davis. Retrieved 08/15/2015.