Changes

'''Beta Acids''' (lupulones) are similar in structure to alpha acids and have the analogous individual beta acids (lupulone, colupulone, adlupulone, prelupulone, and postlupulone <ref name="Dušek_2014">[http://pubs.acs.org/doi/abs/10.1021/jf501852r Qualitative Determination of β‑Acids and Their Transformation Products in Beer and Hop Using HR/AM-LC-MS/MS. Martin Dušek, Jana Olšovská, Karel Krofta, Marie Jurková, and Alexandr Mikyška. 2014.]</ref>) to individual alpha acids. In their original form, beta acids do not contribute to the flavor of beer because they are not soluble in beer unless the pH of the boiling wort is significantly raised to around 7 pH (which is not typical in brewing conditions) and the original gravity is relatively low (2-8°P) <ref name="Bastgen_2019" />. They are also not able to isomerize during wort boiling. Beta acids do not become soluble in wort or beer unless they are chemically modified by a process such as oxidation <ref name="Algazzali_2014" />, nor are they soluble in beer when dry hopping <ref name="Maye_EBC2017">John Paul Maye. EBC 2017 Presentation. 2017.]</ref>. Oxidized beta acids are soluble and can contribute to bitterness in beer. Oxidized beta acids are discussed more under [[Hops#Acids_2|aged hops]]. ====Isomerization of Alpha Acids==== The isomerization of alpha acids into iso-alpha acids is mostly dependent on alpha acid content, time (to a certain extent), temperature, original gravity, and pHhop rate (hop mass), and less so on other IBU saturation. Other variables also affect isomerization to a lesser extent such as time pH and calcium concentration <ref>[https://onlinelibrary.wiley.com/doi/pdf/10.1002/j.2050-0416.1964.tb06356.x CHANGES IN HOP ACIDS CONCENTRATIONS ON HEATING IN AQUEOUS SOLUTIONS AND UNHOPPED WORTS. H. O. Askew. 1964.]</ref><ref>[http://pubs.acs.org/doi/abs/10.1021/jf0481296 Isomerization and Degradation Kinetics of Hop (Humulus lupulus) Acids in a Model Wort-Boiling System. Mark G. Malowicki and Thomas H. Shellhammer. 2005.]</ref><ref name="justice_2018">[https://www.mbaa.com/publications/tq/tqPastIssues/2018/Pages/TQ-55-3-1205-01.aspx Tracking IBU Through the Brewing Process: The Quest for Consistency. Aaron Justus. Director of R&D and Specialty Brewing, Ballast Point Brewing. MBAA TQ 2018; vol. 55, no.3. https://doi.org/10.1094/TQ-55-3-1205-01.]</ref>. The higher the gravity of wortabove 1.050 SG, the more proteins coagulate and drop iso-alpha acids out of solution(lower gravity worts are not affected). During fermentation, yeast cells can absorb iso-alpha acids, which results in further loss of iso-alpha acids in the finished beer <ref name="Bastgen_2019" />. Lower flocculating yeast strains tend to reduce the IBU in finished beer more than high flocculating yeast. Significant isomerization of alpha acids can occur in water without sugar at all (temperatures around boiling are still required), which is relevant in the production of [http://www.garshol.priv.no/blog/331.html "hop tea" in traditional farmhouse brewing] where hops are steeped in hot water for some time, and this is said to extract bitterness from the hops <ref>[http://www.ijbbb.org/papers/161-E005.pdf Kinetic Modeling of Hop Acids during Wort Boiling. Yarong Huang, Johannes Tippmann, and Thomas Becker. 2013.]</ref><ref>[http://www.garshol.priv.no/blog/331.html Lars Marius Garshol. "Raw ale". Larsblog. 05/06/2015. Retrieved 12/17/2018.]</ref>. Malowicki and Shellhammer determined a calculation that predicts the isomerization rates of alpha acids into iso-alpha acids at different temperatures. Beginning at the boiling temperature of 100°C/212°F, which could be considered a rate of 100%, at 96°C/205°F the rate is 72%, and at 90°C/194°F the rate is 43%. This rate continues to drop significantly as the temperature of the wort decreases. At 82°C/180°F isomerization occurs at a rate of 17%. At a temperature of 50°C/122°F, the isomerization rate is at 1%, and finally 0% at 45°C/113°F. This fact has several impacts on brewing processes. For example, when brewing at higher altitudes where the boiling point of wort is less than 100°C/212°F, the isomerization of alpha acids into iso-alpha acids will be reduced to whatever the rate is at that lower temperature. "Hop stands" or "whirlpool additions" where hops are left in contact with hot wort that is less than boiling temperature will continue to isomerize alpha acids <ref>[https://www.mbaa.com/publications/tq/tqPastIssues/2017/Pages/TQ-54-3-0806-01.aspx A Look at Isomerization Reduction Due to Altitude. John Palmer. MBAA TQ 2017 http://dx.doi.org/10.1094/TQ-54-3-0806-01.]</ref>.

The pH of the wort can also have hopping rate (mass) has a significant drastic effect on the isomerization of alpha acids to iso-alpha acids, although less significant than alpha acid content, time (to a certain extent), temperature, and original gravityIBU's for 60 minute additions. Aaron Justice reported a slight rise in higher utilization of when using Polaris hops ("utilization" as being the conversion of 17.6% alpha acids to iso-) versus Tettnang hops (1.9% alpha acids) when the boil pH was raised from 5.05 to 5.35 <ref name="justice_2018">[https://www.mbaa.com/publications/tq/tqPastIssues/2018/Pages/TQ-55-3-1205-01.aspx Tracking IBU Through the Brewing Process: The Quest for Consistency. Aaron Justus. Director of R&D and Specialty Brewing, Ballast Point Brewing. MBAA TQ 2018; vol. 55, no.3. https://doi.org/10.1094/TQ-55-3-1205-01.]</ref>. Bastgen et al. (2019) found that at a boil pH Two beers were brewed using enough of 5.6, the amount each of iso-alpha acids increased by 32% by extending the boil from 60 minutes hop varieties to 120 minutestarget a calculated 40 IBU. However, there was no increase at all in iso-alpha acids when the boil pH was 7, but a pH of 7 is not typical in beer brewed with Polaris hops had 42.6 IBU and the brewing process <ref name="Bastgen_2019" />beer brewed with Tettnang hops had only 28 IBU. Justice also reported that the majority of the more IBU pickup from iso-alpha acids whirlpooling was possible in beers without hops in a 60 minute addition occurs within the first 10 minuteskettle, indicating that IBU saturation can limit IBU's, with only a 12-30% increase after another 50 minutes of boiling (higher gravity beers had more isomerization during the final 50 minutes while lower gravity beers had less isomerization during the final 50 minutes of boiling) maximum IBU being around 100 <ref name="justice_2018" />.

The hopping rate might pH of the wort can also have an a small effect on IBU's for 60 minute additionsthe isomerization of alpha acids to iso-alpha acids, although less significant than alpha acid content, time (to a certain extent), temperature, and original gravity. Aaron Justice reported a higher slight rise in utilization when using Polaris of hops (17.6% "utilization" as being the conversion of alpha acids to iso-alpha acids) versus Tettnang hops (1when the boil pH was raised from 5.05 to 5.9% alph acids)35 <ref name="justice_2018" />. Two beers were brewed using enough Bastgen et al. (2019) found that at a boil pH of each 5.6, the percentage of iso-alpha acids increased by 32% by extending the hop varieties boil from 60 minutes to target a calculated 40 IBU120 minutes. However, there was no increase at all in iso-alpha acids when the boil pH was 7, but a pH of 7 is not typical in the beer brewed with Polaris hops had 42brewing process <ref name="Bastgen_2019" />.6 Time is thought to play a large role in isomerization, however, Justice reported that the majority of the IBU from iso-alpha acids in 60 minute additions and in whirlpool additions occurs within the beer brewed first 10 minutes, with Tettnang hops only a 12-30% increase after another 50 minutes of boiling/whirlpooling (higher gravity beers had more isomerization during the final 50 minutes while lower gravity beers had only 28 IBU less isomerization during the final 50 minutes of boiling) <ref name="justice_2018" />.

'''Beta Acids''' (lupulones) are similar in structure to alpha acids and have the analogous individual beta acids (lupulone, colupulone, adlupulone, prelupulone, and postlupulone <ref name="Dušek_2014">See also:* [http://pubswww.acsthebrewingnetwork.org/doi/abs/10.1021/jf501852r Qualitative Determination of β‑Acids and Their Transformation Products in Beer and Hop Using HRcom/AMbrew-LCstrong-MS/MS. Martin Dušek, Jana Olšovská, Karel Krofta, Marie Jurková, and Alexandr Mikyška. 2014.]</ref>) to individual alpha acids. In their original form, beta acids do not contribute to the flavor of beer because they are not soluble in beer unless the pH of the boiling wort is significantly raised to around 7 pH (which is not typical in brewing conditions) and the original gravity is relatively low (2tracking-8°P) <ref name="Bastgen_2019" />. They are also not able to isomerize during wort boiling. Beta acids do not become soluble in wort or beer unless they are chemically modified by a process such as oxidation <ref name="Algazzali_2014" ibu/>, nor are they soluble in beer when dry hopping <ref name=Brew strong podcast; "Maye_EBC2017Tackling the IBU">John Paul Maye. EBC 2017 Presentation. 2017.]</ref>. Oxidized beta acids are soluble and can contribute to bitterness in beerwith Aaron Justice. Oxidized beta acids are discussed more under [[Hops#Acids_2|aged hops]].