Ferulic acid: Difference between revisions

From Brewing Forward
No edit summary
Tags: Mobile edit Mobile web edit
No edit summary
Tags: Mobile edit Mobile web edit
Line 1: Line 1:
{{In progress}}
{{In progress}}
[[File:Ferulic-acid.png|thumb|Ferulic acid structure]]
[[File:Ferulic-acid.png|thumb|Ferulic acid structure]]
Ferulic acid is one of the main [[phenolic compounds|phenolic]] acids in [[barley]], [[wheat]], and [[rye]] grains (365 to 605 µg/g in barley).<ref name=egi/> It is an effective [[antioxidants|antioxidant]], it  retards the degradation of iso-α-acids, and it is a potent UV light absorber.<ref name=habkos>Habschied K, Košir IJ, Krstanović V, Kumrić G, Mastanjević K. [https://www.mdpi.com/2306-5710/7/2/38 Beer polyphenols—bitterness, astringency, and off-flavors.] ''Beverages.'' 2021;7(2):38.</ref><ref name=bsp/><ref name=Siqueira/> Ferulic acid exists mainly ester-bound to [[arabinoxylans]]; only a minor part of ferulic acid is present in malts in free forms.<ref name=Siqueira>Siqueira PB, Bolini H, Macedo GA. [https://www.researchgate.net/publication/49599952_O_PROCESSO_DE_FABRICACAO_DA_CERVEJA_E_SEUS_EFEITOS_NA_PRESENCA_DE_POLIFENOIS O processo de fabricação da cerveja e seus efeitos na presença de polifenóis. (The beer manufacturing process and its effects on the presence of polyphenols.)] ''Alimentos e nutrição.'' 2008;19(4):491–498.</ref> Some additional ferulic acid can be released from the arabinoxylans by [[enzymes]] during [[mashing]].<ref name=Szwajgier>Szwajgier D. [https://onlinelibrary.wiley.com/doi/pdf/10.1002/j.2050-0416.2011.tb00505.x Dry and wet milling of malt. A preliminary study comparing fermentable sugar, total protein, total phenolics and the ferulic acid content in non-hopped worts.] ''J Inst Brew.'' 2011;117(4):569–577.</ref><ref name=bsp>Briggs DE, Boulton CA, Brookes PA, Stevens R. [[Library|''Brewing Science and Practice.'']] Woodhead Publishing Limited and CRC Press LLC; 2004.</ref><ref name=egi>Egi A, Speers RA, Schwarz PB. [https://www.mbaa.com/publications/tq/tqPastIssues/2004/Abstracts/0803-01.htm Arabinoxylans and their behavior during malting and brewing.] ''Tech Q Master Brew Assoc Am.'' 2004;41(3):248–267.</ref><ref name=vanvan/><ref name=wangas/><ref name=zhao/><ref name=sibpla/> Release is driven by cinnamoyl esterase, an enzyme that is most effective during an extended rest at 40–45°C and pH 5.2–6.6 with stirring.<ref name=cargui/><ref name=wangas>Wannenmacher J, Gastl M, Becker T. [https://ift.onlinelibrary.wiley.com/doi/abs/10.1111/1541-4337.12352 Phenolic substances in beer: Structural diversity, reactive potential and relevance for brewing process and beer quality.] ''Compr Rev Food Sci Food Saf.'' 2018;17(4):953–988.</ref><ref name=vanvan/><ref name=schwarz/> Enzymatic release declines with increasing temperature up to about 65°C where there is none; at this point the amount of free ferulic acid extracted is solely dependent on the free form created during malting.<ref name=vanvan/><ref name=cargui/><ref name=schwarz>Schwarz KJ, Boitz LI, Methner FJ. [https://www.tandfonline.com/doi/abs/10.1094/ASBCJ-2012-1011-02 Release of phenolic acids and amino acids during mashing dependent on temperature, pH, time, and raw materials.] ''J Am Soc Brew Chem.'' 2012;70(4):290–295.</ref> The concentration of ferulic acid remains stable during [[fermentation]] (with typical brewing [[yeast]]), but then delivered during storage.<ref name=szwpie>Szwajgier D, Pielecki J, Targoński Z. [https://onlinelibrary.wiley.com/doi/pdf/10.1002/j.2050-0416.2005.tb00222.x The release of ferulic acid and feruloylated oligosaccharides during wort and beer production.] ''J Inst Brew.'' 2005;111(4):372–379.</ref>
Ferulic acid is one of the main [[phenolic compounds|phenolic]] acids in [[barley]], [[wheat]], and [[rye]] grains (365 to 605 µg/g in barley).<ref name=egi/> It is an effective [[antioxidants|antioxidant]], it  retards the degradation of iso-α-acids, and it is a potent UV light absorber.<ref name=habkos>Habschied K, Košir IJ, Krstanović V, Kumrić G, Mastanjević K. [https://www.mdpi.com/2306-5710/7/2/38 Beer polyphenols—bitterness, astringency, and off-flavors.] ''Beverages.'' 2021;7(2):38.</ref><ref name=bsp/><ref name=Siqueira/> Ferulic acid exists mainly ester-bound to [[arabinoxylans]]; only a minor part of ferulic acid is present in malts in free forms.<ref name=Siqueira>Siqueira PB, Bolini H, Macedo GA. [https://www.researchgate.net/publication/49599952_O_PROCESSO_DE_FABRICACAO_DA_CERVEJA_E_SEUS_EFEITOS_NA_PRESENCA_DE_POLIFENOIS O processo de fabricação da cerveja e seus efeitos na presença de polifenóis. (The beer manufacturing process and its effects on the presence of polyphenols.)] ''Alimentos e nutrição.'' 2008;19(4):491–498.</ref> Some additional ferulic acid can be released from the arabinoxylans by [[enzymes]] during [[mashing]].<ref name=Szwajgier>Szwajgier D. [https://onlinelibrary.wiley.com/doi/pdf/10.1002/j.2050-0416.2011.tb00505.x Dry and wet milling of malt. A preliminary study comparing fermentable sugar, total protein, total phenolics and the ferulic acid content in non-hopped worts.] ''J Inst Brew.'' 2011;117(4):569–577.</ref><ref name=bsp>Briggs DE, Boulton CA, Brookes PA, Stevens R. [[Library|''Brewing Science and Practice.'']] Woodhead Publishing Limited and CRC Press LLC; 2004.</ref><ref name=egi>Egi A, Speers RA, Schwarz PB. [https://www.mbaa.com/publications/tq/tqPastIssues/2004/Abstracts/0803-01.htm Arabinoxylans and their behavior during malting and brewing.] ''Tech Q Master Brew Assoc Am.'' 2004;41(3):248–267.</ref><ref name=vanvan/><ref name=wangas/><ref name=zhao/><ref name=sibpla/> Release is driven by cinnamoyl esterase, an enzyme that is most effective during an extended rest at 40–45°C and pH 5.2–6.6 with stirring.<ref name=cargui/><ref name=wangas>Wannenmacher J, Gastl M, Becker T. [https://ift.onlinelibrary.wiley.com/doi/abs/10.1111/1541-4337.12352 Phenolic substances in beer: Structural diversity, reactive potential and relevance for brewing process and beer quality.] ''Compr Rev Food Sci Food Saf.'' 2018;17(4):953–988.</ref><ref name=vanvan/><ref name=schwarz/> Enzymatic release declines with increasing temperature up to about 65°C where there is none; at this point the amount of free ferulic acid extracted is solely dependent on the free form created during malting.<ref name=vanvan/><ref name=cargui/><ref name=schwarz>Schwarz KJ, Boitz LI, Methner FJ. [https://www.tandfonline.com/doi/abs/10.1094/ASBCJ-2012-1011-02 Release of phenolic acids and amino acids during mashing dependent on temperature, pH, time, and raw materials.] ''J Am Soc Brew Chem.'' 2012;70(4):290–295.</ref> The concentration of ferulic acid remains stable during [[fermentation]] (with typical brewing [[yeast]]), but then declines during storage.<ref name=szwpie>Szwajgier D, Pielecki J, Targoński Z. [https://onlinelibrary.wiley.com/doi/pdf/10.1002/j.2050-0416.2005.tb00222.x The release of ferulic acid and feruloylated oligosaccharides during wort and beer production.] ''J Inst Brew.'' 2005;111(4):372–379.</ref>


Ferulic acid itself is generally flavorless, having a flavor threshold in beer as high as 600 ppm.<ref name=vanvan/> However, it is notable as a precursor to the more flavor-active 4-vinyl guaiacol (4VG). Ferulic acid is transformed into 4VG by decarboxylation, which occurs during boiling to a small extent, but mostly by the enzymes present in many wild microbes and certain strains of brewers yeast, deemed phenolic off-flavor positive (POF+).<ref name=bsp/><ref name=vansai>Vanbeneden N, Saison D, Delvaux F, Delvaux FR. [https://pubs.acs.org/doi/abs/10.1021/jf8019453 Decrease of 4-vinylguaiacol during beer aging and formation of apocynol and vanillin in beer.] ''J Agric Food Chem.'' 2008;56(24):11983–11988.</ref> 4VG gives a spicy clove flavor that is usually undesirable, but is crucial to the flavor profile of some specialty beers. The flavor threshold of 4VG in blond specialty beers is quite low, 0.37 ppm.<ref name=vanvan>Vanbeneden N, Van Roey T, Willems F, Delvaux F, Delvaux FR. [https://www.sciencedirect.com/science/article/abs/pii/S0308814608003348 Release of phenolic flavour precursors during wort production: Influence of process parameters and grist composition on ferulic acid release during brewing.] ''Food Chem.'' 2008;111(1):83–91.</ref>
Ferulic acid itself is generally flavorless, having a flavor threshold in beer as high as 600 ppm.<ref name=vanvan/> However, it is notable as a precursor to the more flavor-active 4-vinyl guaiacol (4VG). Ferulic acid is transformed into 4VG by decarboxylation, which occurs during boiling to a small extent, but mostly by the enzymes present in many wild microbes and certain strains of brewers yeast, deemed phenolic off-flavor positive (POF+).<ref name=bsp/><ref name=vansai>Vanbeneden N, Saison D, Delvaux F, Delvaux FR. [https://pubs.acs.org/doi/abs/10.1021/jf8019453 Decrease of 4-vinylguaiacol during beer aging and formation of apocynol and vanillin in beer.] ''J Agric Food Chem.'' 2008;56(24):11983–11988.</ref> 4VG gives a spicy clove flavor that is usually undesirable, but is crucial to the flavor profile of some specialty beers. The flavor threshold of 4VG in blond specialty beers is quite low, 0.37 ppm.<ref name=vanvan>Vanbeneden N, Van Roey T, Willems F, Delvaux F, Delvaux FR. [https://www.sciencedirect.com/science/article/abs/pii/S0308814608003348 Release of phenolic flavour precursors during wort production: Influence of process parameters and grist composition on ferulic acid release during brewing.] ''Food Chem.'' 2008;111(1):83–91.</ref>

Revision as of 17:08, 20 June 2023

This page is in progress
Please check back later for additional changes
Ferulic acid structure

Ferulic acid is one of the main phenolic acids in barley, wheat, and rye grains (365 to 605 µg/g in barley).[1] It is an effective antioxidant, it retards the degradation of iso-α-acids, and it is a potent UV light absorber.[2][3][4] Ferulic acid exists mainly ester-bound to arabinoxylans; only a minor part of ferulic acid is present in malts in free forms.[4] Some additional ferulic acid can be released from the arabinoxylans by enzymes during mashing.[5][3][1][6][7][8][9] Release is driven by cinnamoyl esterase, an enzyme that is most effective during an extended rest at 40–45°C and pH 5.2–6.6 with stirring.[10][7][6][11] Enzymatic release declines with increasing temperature up to about 65°C where there is none; at this point the amount of free ferulic acid extracted is solely dependent on the free form created during malting.[6][10][11] The concentration of ferulic acid remains stable during fermentation (with typical brewing yeast), but then declines during storage.[12]

Ferulic acid itself is generally flavorless, having a flavor threshold in beer as high as 600 ppm.[6] However, it is notable as a precursor to the more flavor-active 4-vinyl guaiacol (4VG). Ferulic acid is transformed into 4VG by decarboxylation, which occurs during boiling to a small extent, but mostly by the enzymes present in many wild microbes and certain strains of brewers yeast, deemed phenolic off-flavor positive (POF+).[3][13] 4VG gives a spicy clove flavor that is usually undesirable, but is crucial to the flavor profile of some specialty beers. The flavor threshold of 4VG in blond specialty beers is quite low, 0.37 ppm.[6]

During wort boiling, the free wort Ferulic acid (FA) concentration increased by 10%. This net increase was the result of several factors. During wort boiling, thermal decarboxylation of FA will lead to the formation of 4VG. At the end of the boiling process, 0.14 ppm 4VG was found in the wort. This thermal decarboxylation caused the wort FA concentration to diminish by 9%. However, during wort boiling, the wort volume will decrease by 7–8% due to evaporation. This will cause an apparent increase in FA content. Finally, the addition of hop pellets will cause a real increase in wort FA content by 7–11% (based on results obtained in laboratory hop addition experiments). Taking into account these three factors, a net increase of the wort FA content during wort boiling will occur. The reassociation or coprecipitation of free FA with AX, polyphenols or proteins was negligible. Otherwise, no net increase in free FA content would occur during pilot-scale wort boiling. This was confirmed during laboratory-scale wort boiling experiments under reflux (no evaporation) without hop addition. During these experiments, the increase in 4VG corresponded with the decrease in FA.[6]


  • Graf, E. Antioxidant potential of ferulic acid. Free Radic. Biol. Med. 13:435-448, 1992.
  • Kikuzaki, H., Hisamoto, M., Hirose, K., Akiyama, K., and Taniguchi, H. Antioxidant properties of ferulic acid and its related compounds. J. Agric. Food Chem. 50:2161-2168, 2002.

See also

References

  1. ↑ a b Egi A, Speers RA, Schwarz PB. Arabinoxylans and their behavior during malting and brewing. Tech Q Master Brew Assoc Am. 2004;41(3):248–267.
  2. ↑ Habschied K, Košir IJ, Krstanović V, Kumrić G, Mastanjević K. Beer polyphenols—bitterness, astringency, and off-flavors. Beverages. 2021;7(2):38.
  3. ↑ a b c Briggs DE, Boulton CA, Brookes PA, Stevens R. Brewing Science and Practice. Woodhead Publishing Limited and CRC Press LLC; 2004.
  4. ↑ a b Siqueira PB, Bolini H, Macedo GA. O processo de fabricação da cerveja e seus efeitos na presença de polifenóis. (The beer manufacturing process and its effects on the presence of polyphenols.) Alimentos e nutrição. 2008;19(4):491–498.
  5. ↑ Szwajgier D. Dry and wet milling of malt. A preliminary study comparing fermentable sugar, total protein, total phenolics and the ferulic acid content in non-hopped worts. J Inst Brew. 2011;117(4):569–577.
  6. ↑ a b c d e f Vanbeneden N, Van Roey T, Willems F, Delvaux F, Delvaux FR. Release of phenolic flavour precursors during wort production: Influence of process parameters and grist composition on ferulic acid release during brewing. Food Chem. 2008;111(1):83–91.
  7. ↑ a b Wannenmacher J, Gastl M, Becker T. Phenolic substances in beer: Structural diversity, reactive potential and relevance for brewing process and beer quality. Compr Rev Food Sci Food Saf. 2018;17(4):953–988.
  8. ↑ Cite error: Invalid <ref> tag; no text was provided for refs named zhao
  9. ↑ Cite error: Invalid <ref> tag; no text was provided for refs named sibpla
  10. ↑ a b Cite error: Invalid <ref> tag; no text was provided for refs named cargui
  11. ↑ a b Schwarz KJ, Boitz LI, Methner FJ. Release of phenolic acids and amino acids during mashing dependent on temperature, pH, time, and raw materials. J Am Soc Brew Chem. 2012;70(4):290–295.
  12. ↑ Szwajgier D, Pielecki J, Targoński Z. The release of ferulic acid and feruloylated oligosaccharides during wort and beer production. J Inst Brew. 2005;111(4):372–379.
  13. ↑ Vanbeneden N, Saison D, Delvaux F, Delvaux FR. Decrease of 4-vinylguaiacol during beer aging and formation of apocynol and vanillin in beer. J Agric Food Chem. 2008;56(24):11983–11988.
Retrieved from "https://brewingforward.com/index.php?title=Ferulic_acid&oldid=10596"