Ferulic acid: Difference between revisions

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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.<ref name=cargui/><ref name=wangas/><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 phenolic 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>
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.<ref name=cargui/><ref name=wangas/><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>


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/>
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/>