1534-03-8Relevant academic research and scientific papers
The photochemistry of trans-isohumulone, a bitter flavouring component of beer
Weedon, Alan C.,Morrison, John S.
, p. 791 - 798 (2008/12/20)
Methanolic solutions of trans-isohumulone (2), a major bitter flavouring component in beer, were irradiated with UV light of 313 nm wavelength and yielded four primary products containing an enolized cyclic β-triketone moiety: cis-isohumulone (3), humulone (1), dehydro-isohumulone (7), and dehydro-humulinic acid (5). The last of these products results from loss of the 4-methyl-3-pentenoyl side chain of trans-isohumulone. Nine volatile products derived from this side chain were identified and quantitated. The identifications of all photoproducts were confirmed by independent preparation of authentic samples. No evidence of either intramolecular or intermolecular 2+2 cyclo-addition was observed. This work clarifies previous contradictory reports of the products of isohumulone photolysis and provides an example of unexpected photochemistry of an alkenyl-substituted enolized cyclic β-triketone.
The Photolysis of trans-Isohumulone to Dehydrohumulinic Acid, a Key Route to the Development of Sunstruck Flavour in Beer
Bondeel, Georges M. A.,Keukeleire, Denis De,Verzele, Maurice
, p. 2715 - 2719 (2007/10/02)
trans-Isohumulone (2) is photolysed to dehydrohumulonic acid (5) by a Norrish type 1 cleavage, affording a precursor of 3-methylbut-2-ene-1-thiol, the compound responsible for the sunstruck flavour of beer.
BICYCLIC ISOMERIZATION PRODUCTS OF HUMULONE
Velde, M. Van de,Keukeleire, D. De,Bruyn, A. De,Verzele, M.
, p. 223 - 230 (2007/10/02)
The humulone isomerization mixture is investigated by means of efficient preparative High Performance Liquid Chromatography.New bicyclic humulone isomers are isolated and identified (8 and 10 in fig.1).
