Changes

'''Oxidized alpha acids ''' (humulinones) are similar in taste perception to iso-α-acids, but have been described as less bitter (about 66% as bitter) <ref name="Shellhammer, Vollmer and Sharp, CBC 2015"/><ref name="Maye_2016" />. While the taste threshold of iso-alpha acids is 5-6 mg/L in light lager, the threshold for humulinones has been measured to be 8 mg/L in light lager (note that this is an average; tasters vary widely in how much bitterness they perceived from different bitter compounds) <ref name="Algazzali_2014" />. Humulinone content increases in hops after being pelletized (whole leaf hops have less humulinones). In fresh pellet hops that have a relatively low humulinone content, the humulinones contribute little to the bitterness of the beer when boiled, however when dry hopped they readily dissolve into the beer and have a significant impact on the beer's bitterness. With heavy dry hopping, the humulinones also decrease iso-alpha acid content of beer with more than 20 IBU's, but not in beer with less than 25 IBU. The decrease in iso-alpha acids and perceived bitterness/IBU is partially made up for the bitterness of the humulinones themselves (humulinones are picked up in IBU measurements with a [http://chem.libretexts.org/Core/Physical_and_Theoretical_Chemistry/Kinetics/Reaction_Rates/Experimental_Determination_of_Kinetcs/Spectrophotometry spectrophotometer]). In beers with less than 25 IBU, high dry hopping rates greatly increase the bitterness/IBU due to the bitter humulinones. The rate of humulinone formation is limiting, meaning that humulinone formation occurs rapidly during hop pelletization, and the concentration peaks during this time (researchers found that further exposure to air did not increase humulinone content). Scientists believe that this is because when whole leaf hops are baled, only 20% of lupulin glands are broken, whereas when they are pelletized 100% of the lupuline glands are broken. The exact mechanism by which alpha acids are converted to humulinones is not known <ref name="Maye_2016" />. Humulinone content in long-aged hops (1+ years) has not been studied.

'''Oxidized beta acids '' produce some compounds that also contribute to perception of bitterness, specifically hulupones. Unlike humulinones which form relatively quickly from oxidation of alpha acids, hulupones form at a much slower rate <ref name="Dušek_2014" />. Also unlike humulinones, they survive boiling and fermentation. While some sensory analysis of beers containing oxidized beta acids describe the resulting bitterness as "harsh and clinging", another analysis by Krafta et al (2013) described the bitterness of oxidized beta acids in beer when added in their pure form at the beginning of the boil as "pleasant and not lingering". The more degradation of beta acids into oxidized beta acids that occurs in hops, the more bitter beers brewed with these hops will be <ref name="krofta_2013" />. Two other compounds other than hulupones have been identified as being produced by the oxidation of beta acids, epoxycohulupone and epoxyhulupone. Their effect on beer flavor is not yet known, however it is thought that hulupones have the greatest impact on beer flavor <ref name="Dušek_2014" />.