| On the autoxidation of bitter-tasting iso-alpha-acids in beer. | |
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MedLine Citation:
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PMID: 20222658 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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The iso-alpha-acids, the major contributor to bitter beer taste, is well-known to strongly degrade during beer aging. The storage of beer in brown glass bottles revealed a strong depletion of the trans-configured isomers in a highly specific manner, whereas the corresponding cis-iso-alpha-acids seemed to be hardly affected. In comparison, storage of beer in polyethylene terephthalate bottles, which are known to be permeable to oxygen, induced a drastic degradation of both isomers independent of their cis/trans configuration. To investigate the chemical transformation of iso-alpha-acids under oxidative storage conditions, suitable model experiments were performed, and the reaction products that formed were identified as previously not reported hydroperoxy- and hydroxyl-allo-iso-alpha-acids by means of one-/two-dimensional NMR and liquid chromatography-mass spectrometry experiments; for example, cis- and trans-configured hydroperoxy-alloisohumulone as well as the corresponding hydroxy-alloisohumulones were generated upon oxidation of cis- and trans-isohumulone independent of their cis/trans configuration. In addition, the oxidation products formed from the various iso-alpha-acid congeners were quantitatively determined in a series of beer samples stored under defined conditions. For the first time, these data help to understand the molecular mechanism involved in the autoxidative degradation of iso-alpha-acids in beer. |
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Authors:
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Daniel Intelmann; Thomas Hofmann |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Journal of agricultural and food chemistry Volume: 58 ISSN: 1520-5118 ISO Abbreviation: J. Agric. Food Chem. Publication Date: 2010 Apr |
Date Detail:
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Created Date: 2010-04-21 Completed Date: 2010-07-26 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 0374755 Medline TA: J Agric Food Chem Country: United States |
Other Details:
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Languages: eng Pagination: 5059-67 Citation Subset: IM |
Affiliation:
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Food Chemistry and Molecular Sensory Science, Technische Universitat Munchen, Freising, Germany. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Acids
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chemistry* Beer / analysis* Chromatography, Liquid Magnetic Resonance Spectroscopy Mass Spectrometry Oxidation-Reduction |
| Chemical | |
Reg. No./Substance:
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0/Acids |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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