adlupulone
From The Oxford Companion to Beer
is one of four identified beta acid analogues in hop resin, the others being colupulone, lupulone, and prelupulone. Adlupulone levels are low (10% to 15% of total beta acids) but consistent across different varieties. Colupulone levels vary (20% to 55% of total beta acids) depending on variety, as do lupulone levels (30% to 55%). Structurally, these analogues are very similar to their alpha acid counterparts except that beta acids have a third prenyl group attached to the center ring. As a result of this structural difference, these acids do not isomerize and therefore iso-beta acids are not created. Furthermore, beta acids are virtually insoluble in wort; thus, only trace levels can be found in beer. The oxidation products of beta acids (hulupones), however, are present in aged hops and can be found in beer, and they confer bitterness. As hops oxidize, the bitterness that comes from iso-alpha acids diminishes because of alpha acids oxidation, but this is somewhat offset by the presence of bitterness from the hulupones. The ratio of alpha acids to beta acids ultimately dictates to what degree the bitterness will diminish as hops oxidize. Higher levels of beta acids in the raw hops will result in a slower decline of bittering power as hops degrade oxidatively. Qualitatively, however, the bitterness conferred by hulupones is considered coarse.
This definition is from The Oxford Companion to Beer, edited by Garrett Oliver. © Oxford University Press 2012.