Isotope Labeling Studies on the Formation of 5-(Hydroxymethyl)-2-furaldehyde (HMF) from Sucrose by Pyrolysis-GC/MS
Although it is generally assumed that the reactivity of sucrose, a nonreducing sugar, in the Maillard reaction is due to its hydrolysis into free glucose and fructose, however, no direct evidence has been provided for this pathway, especially in dry and high temperature systems. Using specifically 1...
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description | Although it is generally assumed that the reactivity of sucrose, a nonreducing sugar, in the Maillard reaction is due to its hydrolysis into free glucose and fructose, however, no direct evidence has been provided for this pathway, especially in dry and high temperature systems. Using specifically 13C-labeled sucrose at C-1 of the fructose moiety, HMF formation was studied at different temperatures. Under dry pyrolytic conditions and at temperatures above 250 °C, 90% of HMF originated from fructose moiety and only 10% originated from glucose. Alternatively, when sucrose was refluxed in acidic methanol at 65 °C, 100% of HMF was generated from the glucose moiety. Moreover, the relative efficiency of the known HMF precursor 3-deoxyglucosone to generate HMF was compared to that of glucose, fructose and sucrose. Glucose exhibited a much lower conversion rate than 3-deoxyglucosone, however, both fructose and sucrose showed much higher conversion rates than 3-deoxyglucosone thus precluding it as a major precursor of HMF in fructose and sucrose solutions. Based on the data generated, a mechanism of HMF formation from sucrose is proposed. According to this proposal sucrose degrades into glucose and a very reactive fructofuranosyl cation. In dry systems this cation can be effectively converted directly into HMF. |
doi_str_mv | 10.1021/jf8010245 |
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Using specifically 13C-labeled sucrose at C-1 of the fructose moiety, HMF formation was studied at different temperatures. Under dry pyrolytic conditions and at temperatures above 250 °C, 90% of HMF originated from fructose moiety and only 10% originated from glucose. Alternatively, when sucrose was refluxed in acidic methanol at 65 °C, 100% of HMF was generated from the glucose moiety. Moreover, the relative efficiency of the known HMF precursor 3-deoxyglucosone to generate HMF was compared to that of glucose, fructose and sucrose. Glucose exhibited a much lower conversion rate than 3-deoxyglucosone, however, both fructose and sucrose showed much higher conversion rates than 3-deoxyglucosone thus precluding it as a major precursor of HMF in fructose and sucrose solutions. Based on the data generated, a mechanism of HMF formation from sucrose is proposed. According to this proposal sucrose degrades into glucose and a very reactive fructofuranosyl cation. In dry systems this cation can be effectively converted directly into HMF.</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/jf8010245</identifier><identifier>PMID: 18611024</identifier><identifier>CODEN: JAFCAU</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>3-deoxyglucosone ; 5-(hydroxymethyl)-2-furaldehyde ; aldehydes ; Biological and medical sciences ; carbon ; Carbon Isotopes ; cations ; chemical reactions ; Food Chemistry/Biochemistry ; Food industries ; fructofuranosyl cation ; fructose ; Fructose - chemistry ; fructose and sucrose ; Fundamental and applied biological sciences. Psychology ; Furaldehyde - analogs & derivatives ; Furaldehyde - chemical synthesis ; gas chromatography ; Gas Chromatography-Mass Spectrometry ; glucose ; Glucose - chemistry ; HMF formation mechanism from glucose ; Hot Temperature ; Hydrolysis ; Isotope Labeling ; Isotope labeling studies ; levoglucosan formation ; Maillard reaction ; mass spectrometry ; pyrolysis ; reducing sugars ; Solutions ; stable isotopes ; sucrose ; Sucrose - chemistry ; temperature ; water content</subject><ispartof>Journal of agricultural and food chemistry, 2008-08, Vol.56 (15), p.6717-6723</ispartof><rights>Copyright © 2008 American Chemical Society</rights><rights>2008 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a471t-aaf0023c6ebcabe056362455d9563c0b8ce2108b73dcda331dc4a2e1474928d43</citedby><cites>FETCH-LOGICAL-a471t-aaf0023c6ebcabe056362455d9563c0b8ce2108b73dcda331dc4a2e1474928d43</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jf8010245$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jf8010245$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=20577246$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/18611024$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Perez Locas, Carolina</creatorcontrib><creatorcontrib>Yaylayan, Varoujan A.</creatorcontrib><title>Isotope Labeling Studies on the Formation of 5-(Hydroxymethyl)-2-furaldehyde (HMF) from Sucrose by Pyrolysis-GC/MS</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>Although it is generally assumed that the reactivity of sucrose, a nonreducing sugar, in the Maillard reaction is due to its hydrolysis into free glucose and fructose, however, no direct evidence has been provided for this pathway, especially in dry and high temperature systems. Using specifically 13C-labeled sucrose at C-1 of the fructose moiety, HMF formation was studied at different temperatures. Under dry pyrolytic conditions and at temperatures above 250 °C, 90% of HMF originated from fructose moiety and only 10% originated from glucose. Alternatively, when sucrose was refluxed in acidic methanol at 65 °C, 100% of HMF was generated from the glucose moiety. Moreover, the relative efficiency of the known HMF precursor 3-deoxyglucosone to generate HMF was compared to that of glucose, fructose and sucrose. Glucose exhibited a much lower conversion rate than 3-deoxyglucosone, however, both fructose and sucrose showed much higher conversion rates than 3-deoxyglucosone thus precluding it as a major precursor of HMF in fructose and sucrose solutions. Based on the data generated, a mechanism of HMF formation from sucrose is proposed. According to this proposal sucrose degrades into glucose and a very reactive fructofuranosyl cation. In dry systems this cation can be effectively converted directly into HMF.</description><subject>3-deoxyglucosone</subject><subject>5-(hydroxymethyl)-2-furaldehyde</subject><subject>aldehydes</subject><subject>Biological and medical sciences</subject><subject>carbon</subject><subject>Carbon Isotopes</subject><subject>cations</subject><subject>chemical reactions</subject><subject>Food Chemistry/Biochemistry</subject><subject>Food industries</subject><subject>fructofuranosyl cation</subject><subject>fructose</subject><subject>Fructose - chemistry</subject><subject>fructose and sucrose</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Furaldehyde - analogs & derivatives</subject><subject>Furaldehyde - chemical synthesis</subject><subject>gas chromatography</subject><subject>Gas Chromatography-Mass Spectrometry</subject><subject>glucose</subject><subject>Glucose - chemistry</subject><subject>HMF formation mechanism from glucose</subject><subject>Hot Temperature</subject><subject>Hydrolysis</subject><subject>Isotope Labeling</subject><subject>Isotope labeling studies</subject><subject>levoglucosan formation</subject><subject>Maillard reaction</subject><subject>mass spectrometry</subject><subject>pyrolysis</subject><subject>reducing sugars</subject><subject>Solutions</subject><subject>stable isotopes</subject><subject>sucrose</subject><subject>Sucrose - chemistry</subject><subject>temperature</subject><subject>water content</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkF9v0zAUxS0EYmXwwBcAv4DWBzPbif_kESraTnRiUjaJN8uxnTUliTs7kZZvj6tW3QtPvtb93XPPPQB8JPgbwZRc72qJU5GzV2BGGMWIESJfgxlOTSQZJxfgXYw7jLFkAr8FF0RychiYgXAT_eD3Dm505dqmf4TlMNrGReh7OGwdXPrQ6aFJP19Dhq7Wkw3-eercsJ3aOaKoHoNurdtO1sGr9e1yDuvgO1iOJvjoYDXBuyn4dopNRKvF9W35HrypdRvdh9N7CR6WP-8Xa7T5vbpZfN8gnQsyIK3r5D8z3FUmecOMZzydyGyRKoMraRwlWFYis8bqLCPW5Jo6kou8oNLm2SX4etTdB_80ujioronGta3unR-j4kWOMWMigfMjeHAcg6vVPjSdDpMiWB0CVueAE_vpJDpWnbMv5CnRBHw5AToa3dZB96aJZ45iJgTNeeLQkWvi4J7PfR3-Ki4ywdT9XanE6k9W_OBC_Ur85yNfa6_0Y0iaDyXFJMO4oFxK8bJZm6h2fgx9Svc_J_wD2Lak7Q</recordid><startdate>20080813</startdate><enddate>20080813</enddate><creator>Perez Locas, Carolina</creator><creator>Yaylayan, Varoujan A.</creator><general>American Chemical Society</general><scope>FBQ</scope><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20080813</creationdate><title>Isotope Labeling Studies on the Formation of 5-(Hydroxymethyl)-2-furaldehyde (HMF) from Sucrose by Pyrolysis-GC/MS</title><author>Perez Locas, Carolina ; Yaylayan, Varoujan A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a471t-aaf0023c6ebcabe056362455d9563c0b8ce2108b73dcda331dc4a2e1474928d43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>3-deoxyglucosone</topic><topic>5-(hydroxymethyl)-2-furaldehyde</topic><topic>aldehydes</topic><topic>Biological and medical sciences</topic><topic>carbon</topic><topic>Carbon Isotopes</topic><topic>cations</topic><topic>chemical reactions</topic><topic>Food Chemistry/Biochemistry</topic><topic>Food industries</topic><topic>fructofuranosyl cation</topic><topic>fructose</topic><topic>Fructose - chemistry</topic><topic>fructose and sucrose</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Furaldehyde - analogs & derivatives</topic><topic>Furaldehyde - chemical synthesis</topic><topic>gas chromatography</topic><topic>Gas Chromatography-Mass Spectrometry</topic><topic>glucose</topic><topic>Glucose - chemistry</topic><topic>HMF formation mechanism from glucose</topic><topic>Hot Temperature</topic><topic>Hydrolysis</topic><topic>Isotope Labeling</topic><topic>Isotope labeling studies</topic><topic>levoglucosan formation</topic><topic>Maillard reaction</topic><topic>mass spectrometry</topic><topic>pyrolysis</topic><topic>reducing sugars</topic><topic>Solutions</topic><topic>stable isotopes</topic><topic>sucrose</topic><topic>Sucrose - chemistry</topic><topic>temperature</topic><topic>water content</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Perez Locas, Carolina</creatorcontrib><creatorcontrib>Yaylayan, Varoujan A.</creatorcontrib><collection>AGRIS</collection><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of agricultural and food chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Perez Locas, Carolina</au><au>Yaylayan, Varoujan A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Isotope Labeling Studies on the Formation of 5-(Hydroxymethyl)-2-furaldehyde (HMF) from Sucrose by Pyrolysis-GC/MS</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2008-08-13</date><risdate>2008</risdate><volume>56</volume><issue>15</issue><spage>6717</spage><epage>6723</epage><pages>6717-6723</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><coden>JAFCAU</coden><abstract>Although it is generally assumed that the reactivity of sucrose, a nonreducing sugar, in the Maillard reaction is due to its hydrolysis into free glucose and fructose, however, no direct evidence has been provided for this pathway, especially in dry and high temperature systems. Using specifically 13C-labeled sucrose at C-1 of the fructose moiety, HMF formation was studied at different temperatures. Under dry pyrolytic conditions and at temperatures above 250 °C, 90% of HMF originated from fructose moiety and only 10% originated from glucose. Alternatively, when sucrose was refluxed in acidic methanol at 65 °C, 100% of HMF was generated from the glucose moiety. Moreover, the relative efficiency of the known HMF precursor 3-deoxyglucosone to generate HMF was compared to that of glucose, fructose and sucrose. Glucose exhibited a much lower conversion rate than 3-deoxyglucosone, however, both fructose and sucrose showed much higher conversion rates than 3-deoxyglucosone thus precluding it as a major precursor of HMF in fructose and sucrose solutions. Based on the data generated, a mechanism of HMF formation from sucrose is proposed. According to this proposal sucrose degrades into glucose and a very reactive fructofuranosyl cation. In dry systems this cation can be effectively converted directly into HMF.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>18611024</pmid><doi>10.1021/jf8010245</doi><tpages>7</tpages></addata></record> |
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subjects | 3-deoxyglucosone 5-(hydroxymethyl)-2-furaldehyde aldehydes Biological and medical sciences carbon Carbon Isotopes cations chemical reactions Food Chemistry/Biochemistry Food industries fructofuranosyl cation fructose Fructose - chemistry fructose and sucrose Fundamental and applied biological sciences. Psychology Furaldehyde - analogs & derivatives Furaldehyde - chemical synthesis gas chromatography Gas Chromatography-Mass Spectrometry glucose Glucose - chemistry HMF formation mechanism from glucose Hot Temperature Hydrolysis Isotope Labeling Isotope labeling studies levoglucosan formation Maillard reaction mass spectrometry pyrolysis reducing sugars Solutions stable isotopes sucrose Sucrose - chemistry temperature water content |
title | Isotope Labeling Studies on the Formation of 5-(Hydroxymethyl)-2-furaldehyde (HMF) from Sucrose by Pyrolysis-GC/MS |
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