Model Studies on the Photosensitized Isomerization of Bixin
The photosensitized isomerization reaction of the natural cis carotenoid bixin (methyl hydrogen 9‘-cis-6, 6‘-diapocarotene-6, 6‘-dioate) with rose bengal or methylene blue as the sensitizer in acetonitrile/methanol (1:1) solution was studied using UV−vis spectroscopy, high-performance liquid chromat...
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| Veröffentlicht in: | Journal of agricultural and food chemistry 2004-01, Vol.52 (2), p.367-373 |
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| container_title | Journal of agricultural and food chemistry |
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| creator | Montenegro, Mariana A Rios, Alessandro de O Mercadante, Adriana Z Nazareno, Mónica A Borsarelli, Claudio D |
| description | The photosensitized isomerization reaction of the natural cis carotenoid bixin (methyl hydrogen 9‘-cis-6, 6‘-diapocarotene-6, 6‘-dioate) with rose bengal or methylene blue as the sensitizer in acetonitrile/methanol (1:1) solution was studied using UV−vis spectroscopy, high-performance liquid chromatography (HPLC), and time-resolved spectroscopic techniques, such as laser-flash photolysis and singlet oxygen phosphorescence detection. In both N2- and air-saturated solutions, the main product formed was all-trans-bixin. The observed isomerization rate constants, k obs, decreased in the presence of air or with increase in the bixin concentration, suggesting the participation of the excited triplet state of bixin, 3Bix*, as precursor of the cis→ trans process. On the other hand, bixin solutions in the absence of sensitizer and/or light did not degrade, indicating that the ground state of bixin is stable to thermal isomerization at room temperature. Time-resolved spectroscopic experiments confirmed the formation of the excited triplet state of bixin and its deactivation by ground state bixin and molecular oxygen quenching processes. The primary isomerization products only degraded in the presence of air and under prolonged illumination conditions, probably due to the formation of oxidation products by reaction with singlet molecular oxygen. An energy-transfer mechanism was used to explain the observed results for the bixin transformations, and the consequences for food color are discussed. Keywords: Bixin; photoisomerization; photosensitization; singlet oxygen and triplet states |
| doi_str_mv | 10.1021/jf0349026 |
| format | Article |
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In both N2- and air-saturated solutions, the main product formed was all-trans-bixin. The observed isomerization rate constants, k obs, decreased in the presence of air or with increase in the bixin concentration, suggesting the participation of the excited triplet state of bixin, 3Bix*, as precursor of the cis→ trans process. On the other hand, bixin solutions in the absence of sensitizer and/or light did not degrade, indicating that the ground state of bixin is stable to thermal isomerization at room temperature. Time-resolved spectroscopic experiments confirmed the formation of the excited triplet state of bixin and its deactivation by ground state bixin and molecular oxygen quenching processes. The primary isomerization products only degraded in the presence of air and under prolonged illumination conditions, probably due to the formation of oxidation products by reaction with singlet molecular oxygen. An energy-transfer mechanism was used to explain the observed results for the bixin transformations, and the consequences for food color are discussed. Keywords: Bixin; photoisomerization; photosensitization; singlet oxygen and triplet states</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/jf0349026</identifier><identifier>PMID: 14733523</identifier><identifier>CODEN: JAFCAU</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Biological and medical sciences ; Carotenoids - chemistry ; Chromatography, High Pressure Liquid ; Food additives ; Food industries ; Fundamental and applied biological sciences. Psychology ; General aspects ; Isomerism ; Kinetics ; Light ; Methylene Blue - chemistry ; Models, Chemical ; Oxidation-Reduction ; Photolysis ; Photosensitizing Agents ; Rose Bengal - chemistry ; Solutions</subject><ispartof>Journal of agricultural and food chemistry, 2004-01, Vol.52 (2), p.367-373</ispartof><rights>Copyright © 2004 American Chemical Society</rights><rights>2004 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a379t-291ef89a492978eeca2ee04d48cf1a8f84f63a54173fe70a244f6e9242d389943</citedby><cites>FETCH-LOGICAL-a379t-291ef89a492978eeca2ee04d48cf1a8f84f63a54173fe70a244f6e9242d389943</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/jf0349026$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jf0349026$$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=15410609$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/14733523$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Montenegro, Mariana A</creatorcontrib><creatorcontrib>Rios, Alessandro de O</creatorcontrib><creatorcontrib>Mercadante, Adriana Z</creatorcontrib><creatorcontrib>Nazareno, Mónica A</creatorcontrib><creatorcontrib>Borsarelli, Claudio D</creatorcontrib><title>Model Studies on the Photosensitized Isomerization of Bixin</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>The photosensitized isomerization reaction of the natural cis carotenoid bixin (methyl hydrogen 9‘-cis-6, 6‘-diapocarotene-6, 6‘-dioate) with rose bengal or methylene blue as the sensitizer in acetonitrile/methanol (1:1) solution was studied using UV−vis spectroscopy, high-performance liquid chromatography (HPLC), and time-resolved spectroscopic techniques, such as laser-flash photolysis and singlet oxygen phosphorescence detection. In both N2- and air-saturated solutions, the main product formed was all-trans-bixin. The observed isomerization rate constants, k obs, decreased in the presence of air or with increase in the bixin concentration, suggesting the participation of the excited triplet state of bixin, 3Bix*, as precursor of the cis→ trans process. On the other hand, bixin solutions in the absence of sensitizer and/or light did not degrade, indicating that the ground state of bixin is stable to thermal isomerization at room temperature. Time-resolved spectroscopic experiments confirmed the formation of the excited triplet state of bixin and its deactivation by ground state bixin and molecular oxygen quenching processes. The primary isomerization products only degraded in the presence of air and under prolonged illumination conditions, probably due to the formation of oxidation products by reaction with singlet molecular oxygen. An energy-transfer mechanism was used to explain the observed results for the bixin transformations, and the consequences for food color are discussed. Keywords: Bixin; photoisomerization; photosensitization; singlet oxygen and triplet states</description><subject>Biological and medical sciences</subject><subject>Carotenoids - chemistry</subject><subject>Chromatography, High Pressure Liquid</subject><subject>Food additives</subject><subject>Food industries</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>General aspects</subject><subject>Isomerism</subject><subject>Kinetics</subject><subject>Light</subject><subject>Methylene Blue - chemistry</subject><subject>Models, Chemical</subject><subject>Oxidation-Reduction</subject><subject>Photolysis</subject><subject>Photosensitizing Agents</subject><subject>Rose Bengal - chemistry</subject><subject>Solutions</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0E1PGzEQBmALFZU07YE_gPbSSj0sjD92bYsTRP1AAoGU9JKLZXbHwmGzBntXgvx6XCUiF06WZh69Gr-EHFM4pcDo2coBFxpYfUAmtGJQVpSqT2QCeVmqqqZH5EtKKwBQlYTP5IgKyXnF-ISc34QWu2I-jK3HVIS-GB6wuHsIQ0jYJz_4DbbFVQprjH5jB59FcMWlf_H9V3LobJfw2-6dkn-_fy1mf8vr2z9Xs4vr0nKph5Jpik5pKzTTUiE2liGCaIVqHLXKKeFqbitBJXcowTKRB6iZYC1XWgs-JT-2uU8xPI-YBrP2qcGusz2GMRkFNH-M0wx_bmETQ0oRnXmKfm3jq6Fg_jdl3pvK9mQXOt6vsd3LXTUZfN8BmxrbuWj7xqe9ywdDDTq7cut8GvDlfW_jo6kll5VZ3M0NVJLP5Hxplvtc2ySzCmPsc3cfHPgGJqiJdA</recordid><startdate>20040128</startdate><enddate>20040128</enddate><creator>Montenegro, Mariana A</creator><creator>Rios, Alessandro de O</creator><creator>Mercadante, Adriana Z</creator><creator>Nazareno, Mónica A</creator><creator>Borsarelli, Claudio D</creator><general>American Chemical Society</general><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>20040128</creationdate><title>Model Studies on the Photosensitized Isomerization of Bixin</title><author>Montenegro, Mariana A ; Rios, Alessandro de O ; Mercadante, Adriana Z ; Nazareno, Mónica A ; Borsarelli, Claudio D</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a379t-291ef89a492978eeca2ee04d48cf1a8f84f63a54173fe70a244f6e9242d389943</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Biological and medical sciences</topic><topic>Carotenoids - chemistry</topic><topic>Chromatography, High Pressure Liquid</topic><topic>Food additives</topic><topic>Food industries</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>General aspects</topic><topic>Isomerism</topic><topic>Kinetics</topic><topic>Light</topic><topic>Methylene Blue - chemistry</topic><topic>Models, Chemical</topic><topic>Oxidation-Reduction</topic><topic>Photolysis</topic><topic>Photosensitizing Agents</topic><topic>Rose Bengal - chemistry</topic><topic>Solutions</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Montenegro, Mariana A</creatorcontrib><creatorcontrib>Rios, Alessandro de O</creatorcontrib><creatorcontrib>Mercadante, Adriana Z</creatorcontrib><creatorcontrib>Nazareno, Mónica A</creatorcontrib><creatorcontrib>Borsarelli, Claudio D</creatorcontrib><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>Montenegro, Mariana A</au><au>Rios, Alessandro de O</au><au>Mercadante, Adriana Z</au><au>Nazareno, Mónica A</au><au>Borsarelli, Claudio D</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Model Studies on the Photosensitized Isomerization of Bixin</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2004-01-28</date><risdate>2004</risdate><volume>52</volume><issue>2</issue><spage>367</spage><epage>373</epage><pages>367-373</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><coden>JAFCAU</coden><abstract>The photosensitized isomerization reaction of the natural cis carotenoid bixin (methyl hydrogen 9‘-cis-6, 6‘-diapocarotene-6, 6‘-dioate) with rose bengal or methylene blue as the sensitizer in acetonitrile/methanol (1:1) solution was studied using UV−vis spectroscopy, high-performance liquid chromatography (HPLC), and time-resolved spectroscopic techniques, such as laser-flash photolysis and singlet oxygen phosphorescence detection. In both N2- and air-saturated solutions, the main product formed was all-trans-bixin. The observed isomerization rate constants, k obs, decreased in the presence of air or with increase in the bixin concentration, suggesting the participation of the excited triplet state of bixin, 3Bix*, as precursor of the cis→ trans process. On the other hand, bixin solutions in the absence of sensitizer and/or light did not degrade, indicating that the ground state of bixin is stable to thermal isomerization at room temperature. Time-resolved spectroscopic experiments confirmed the formation of the excited triplet state of bixin and its deactivation by ground state bixin and molecular oxygen quenching processes. The primary isomerization products only degraded in the presence of air and under prolonged illumination conditions, probably due to the formation of oxidation products by reaction with singlet molecular oxygen. An energy-transfer mechanism was used to explain the observed results for the bixin transformations, and the consequences for food color are discussed. Keywords: Bixin; photoisomerization; photosensitization; singlet oxygen and triplet states</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>14733523</pmid><doi>10.1021/jf0349026</doi><tpages>7</tpages></addata></record> |
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| subjects | Biological and medical sciences Carotenoids - chemistry Chromatography, High Pressure Liquid Food additives Food industries Fundamental and applied biological sciences. Psychology General aspects Isomerism Kinetics Light Methylene Blue - chemistry Models, Chemical Oxidation-Reduction Photolysis Photosensitizing Agents Rose Bengal - chemistry Solutions |
| title | Model Studies on the Photosensitized Isomerization of Bixin |
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