Isohumulone

Isohumulones are chemical compounds that contribute to the bitter taste of beer and are in the class of compounds known as iso-alpha acids. They are found in hops.

Isohumulone
Names
IUPAC name
3,4-Dihydroxy-5-(3-methylbut- 2-enyl)-2-(3-methyl-1-oxobutyl)-4-(4- methyl-1-oxopent-3-enyl)-1- cyclopent-2-enone[1]
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.042.778
UNII
  • InChI=1S/C21H30O5/c1-12(2)7-9-15-19(24)18(16(22)11-14(5)6)20(25)21(15,26)17(23)10-8-13(3)4/h7-8,14-15,25-26H,9-11H2,1-6H3 checkY
    Key: QARXXMMQVDCYGZ-UHFFFAOYSA-N checkY
  • InChI=1/C21H30O5/c1-12(2)7-9-15-19(24)18(16(22)11-14(5)6)20(25)21(15,26)17(23)10-8-13(3)4/h7-8,14-15,25-26H,9-11H2,1-6H3
    Key: QARXXMMQVDCYGZ-UHFFFAOYAV
  • O=C(C1(O)C(/O)=C(\C(=O)C1C/C=C(/C)C)C(=O)CC(C)C)C\C=C(/C)C
Properties
C21H30O5
Molar mass 362.466 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Beer

The bitterness of beer is measured according to the International Bitterness Units scale, with one IBU corresponding to one part-per-million of isohumulone. When beer is exposed to light, these compounds can decompose in a reaction catalyzed by riboflavin to generate free-radical species by the homolytic cleavage of the exocyclic carbon-carbon bond. The cleaved acyl side-chain radical then decomposes further, expelling carbon monoxide and generating 1,1-dimethylallyl radical. This radical can finally react with sulfur-containing amino acids, such as cysteine, to create 3-methylbut-2-ene-1-thiol, a thiol which causes beer to develop a "skunky" flavor.[2]

Formation

Isohumulones are generated by the isomerization of humulone.[1][3][4]

Isomerization of humulone to cis- and trans-isohumulone

See also

References
  1. Urban, Jan; Dahlberg, Clinton; Carroll, Brian; Kaminsky, Werner (2013). "Absolute Configuration of Beer′s Bitter Compounds". Angew. Chem. Int. Ed. 52 (5): 1553–1555. doi:10.1002/anie.201208450. PMC 3563212. PMID 23239507.
  2. "UNC chemists figure out what causes 'skunky beer'". eurekalert.org.
  3. Blanco, Carlos A.; Rojas, Antonio; Caballero, Pedro A.; Ronda, Felicidad; Gomez, Manuel; Caballero, Isabel (2006). "A better control of beer properties by predicting acidity of hop iso-α-acids". Trends in Food Science & Technology. 17 (7): 373. doi:10.1016/j.tifs.2005.11.012.
  4. Esslinger, H. M. and Narziss, L. 2003. “Beer.” in Ullmann's Encyclopedia of Industrial Chemistry. Wiley-VCH Verlag GmbH & Co. KGaA, 2009 doi:10.1002/14356007.a03_421
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