Evidence is presented to support 2,3-dlhydro-3,5-dihydroxy-6-methyl-4 H -pyran-4-one as the structure of a previously isolated, hexose degradation-pr
Published mass spectra of carboxylic acids are generally not easy to locate because acids are often converted to their more volatile methyl ester derivatives prior to determination of the mass spectra. However, this esterification procedure is usually not possible when natural product mixtures are being separated by gas chromatography.
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTBase-catalyzed fructose degradation and its relation to nonenzymic browningPhilip E. Shaw, James H. Tatum, and Robert E. BerryCite this: J. Agric. Food Chem. 1968, 16, 6, 979–982Publication Date (Print):November 1, 1968Publication History Published online1 May 2002Published inissue 1 November 1968https://doi.org/10.1021/jf60160a014Request reuse permissionsArticle Views390Altmetric-Citations69LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (385 KB) Get e-Alertsclose Get e-Alerts
Interest in nonenzymic browning of dehydrated food-products led to this study of the acid-catalyzed degradation of d-fructose. The two major furan derivatives formed in this degradation are 5-(hydroxymethyl)-2-furaldehyde and 2-(2-hydroxyacetyl)furan. Several minor products were identified. These included furfural, 5-methyl-2-furaldehyde, isomaltol, 2-(2-hydroxyacetyl)furan formate, and 4-hydroxy-2,3,5-hexanetrione (acetylformoin). Formic acid, acetic acid, and levulinic acid were also present. A new hydroxyfuranone has been isolated, and evidence is presented supporting its structure. Degradation studies at pH 1.0, 2.15, and 3.5 showed a variation in the minor components formed. The mechanism for formation of the furan derivatives is discussed.
