Abstract
Gas chromatograms of the isopropyl esters of the acids obtained from α and β acids by oxidation or pyrolysis indicate the presence of small amounts of some additional analogues of humulone and lupulone; countercurrent distribution of the α acid group has provided fractions which are greatly enriched in these minor analogues. The countercurrent distribution fraction conforming to prehumulone yields isocaproic and n-caproic acids on oxidation, and the β acid group likewise contains two corresponding analogues of lupulone; prehumulone and prelupulone are therefore almost certainly mixtures of isocaproyl and n-caproyl analogues of humulone and lupulone. The β acid group yields a small amount of n-propionic acid, indicating the presence of postlupulone, corresponding to the presence of posthumulone in the α acid group reported by Verzele and also confirmed here; small amounts of humulone and lupulone analogues bearing n-butyryl side chains appear to be present also. Evidence has been obtained also which supports the existence of 4-desoxycohumulone and 4-desoxyadhumulone and indicates, in addition, the presence of other additional analogues corresponding to those now found in the α and β acid groups.
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