Purification of 2-Monoacylglycerols Using Liquid CO2 Extraction
The fatty acid moiety of 2-monoacyl-sn-glycerol (2-MAG) undergoes spontaneous acyl migration to the sn-1(3) position, resulting in a thermodynamic equilibrium of approximately 1:9 of 2-MAG to 1(3)-monoacyl-sn-glycerol (1-MAG). Spontaneous acyl migration is an impediment to synthesizing and isolating...
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| Veröffentlicht in: | Journal of the American Oil Chemists' Society 2012-08, Vol.89 (8), p.1529-1536 |
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| creator | Compton, David L Eller, Fred J Laszlo, Joseph A Evans, Kervin O |
| description | The fatty acid moiety of 2-monoacyl-sn-glycerol (2-MAG) undergoes spontaneous acyl migration to the sn-1(3) position, resulting in a thermodynamic equilibrium of approximately 1:9 of 2-MAG to 1(3)-monoacyl-sn-glycerol (1-MAG). Spontaneous acyl migration is an impediment to synthesizing and isolating specific 2-MAG for use as intermediates in the synthesis of structured triacylglycerols. 2-Monooleoyl-sn-glycerol was synthesized by the enzymatic ethanolysis of triolein and isolated by liquid CO2 extraction. The resultant MAG, diacylglycerol, and fatty acid ethyl esters were quantified by 1H NMR and supercritical fluid chromatography. The low polarity of the CO2 and mild extraction temperature (25 °C) resulted in very low spontaneous acyl migration rates, allowing the MAG to be isolated in 80% yield and in a very high 2-MAG:1-MAG ratios of ≥93 mol%. |
| doi_str_mv | 10.1007/s11746-012-2035-9 |
| format | Article |
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Spontaneous acyl migration is an impediment to synthesizing and isolating specific 2-MAG for use as intermediates in the synthesis of structured triacylglycerols. 2-Monooleoyl-sn-glycerol was synthesized by the enzymatic ethanolysis of triolein and isolated by liquid CO2 extraction. The resultant MAG, diacylglycerol, and fatty acid ethyl esters were quantified by 1H NMR and supercritical fluid chromatography. The low polarity of the CO2 and mild extraction temperature (25 °C) resulted in very low spontaneous acyl migration rates, allowing the MAG to be isolated in 80% yield and in a very high 2-MAG:1-MAG ratios of ≥93 mol%.</description><identifier>ISSN: 0003-021X</identifier><identifier>EISSN: 1558-9331</identifier><identifier>DOI: 10.1007/s11746-012-2035-9</identifier><language>eng</language><publisher>Berlin/Heidelberg: Springer-Verlag</publisher><subject>2‐Monoacylglycerol ; Acyl migration ; Agriculture ; Biological and medical sciences ; Biomaterials ; Biotechnology ; Carbon dioxide ; Chemistry ; Chemistry and Materials Science ; Chromatography ; Esters ; ethanolysis ; Fat industries ; Fatty acids ; Food engineering ; Food industries ; Food Science ; Fundamental and applied biological sciences. Psychology ; General aspects ; Industrial Chemistry/Chemical Engineering ; Lipids ; Liquid CO2 ; NMR ; Nuclear magnetic resonance ; nuclear magnetic resonance spectroscopy ; Original Paper ; Structured lipids ; supercritical fluid chromatography ; temperature ; Thermodynamics ; triolein</subject><ispartof>Journal of the American Oil Chemists' Society, 2012-08, Vol.89 (8), p.1529-1536</ispartof><rights>AOCS (outside the USA) 2012</rights><rights>2012 American Oil Chemists' Society (AOCS)</rights><rights>2015 INIST-CNRS</rights><rights>AOCS 2012</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-f2829-1109be1e822842b363a89f66dec0be33b69c71d63bc802f7c5245aebc192cfa33</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s11746-012-2035-9$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s11746-012-2035-9$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,778,782,1414,27907,27908,41471,42540,45557,45558,51302</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=26207516$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Compton, David L</creatorcontrib><creatorcontrib>Eller, Fred J</creatorcontrib><creatorcontrib>Laszlo, Joseph A</creatorcontrib><creatorcontrib>Evans, Kervin O</creatorcontrib><title>Purification of 2-Monoacylglycerols Using Liquid CO2 Extraction</title><title>Journal of the American Oil Chemists' Society</title><addtitle>J Am Oil Chem Soc</addtitle><description>The fatty acid moiety of 2-monoacyl-sn-glycerol (2-MAG) undergoes spontaneous acyl migration to the sn-1(3) position, resulting in a thermodynamic equilibrium of approximately 1:9 of 2-MAG to 1(3)-monoacyl-sn-glycerol (1-MAG). Spontaneous acyl migration is an impediment to synthesizing and isolating specific 2-MAG for use as intermediates in the synthesis of structured triacylglycerols. 2-Monooleoyl-sn-glycerol was synthesized by the enzymatic ethanolysis of triolein and isolated by liquid CO2 extraction. The resultant MAG, diacylglycerol, and fatty acid ethyl esters were quantified by 1H NMR and supercritical fluid chromatography. The low polarity of the CO2 and mild extraction temperature (25 °C) resulted in very low spontaneous acyl migration rates, allowing the MAG to be isolated in 80% yield and in a very high 2-MAG:1-MAG ratios of ≥93 mol%.</description><subject>2‐Monoacylglycerol</subject><subject>Acyl migration</subject><subject>Agriculture</subject><subject>Biological and medical sciences</subject><subject>Biomaterials</subject><subject>Biotechnology</subject><subject>Carbon dioxide</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chromatography</subject><subject>Esters</subject><subject>ethanolysis</subject><subject>Fat industries</subject><subject>Fatty acids</subject><subject>Food engineering</subject><subject>Food industries</subject><subject>Food Science</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>General aspects</subject><subject>Industrial Chemistry/Chemical Engineering</subject><subject>Lipids</subject><subject>Liquid CO2</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>nuclear magnetic resonance spectroscopy</subject><subject>Original Paper</subject><subject>Structured lipids</subject><subject>supercritical fluid chromatography</subject><subject>temperature</subject><subject>Thermodynamics</subject><subject>triolein</subject><issn>0003-021X</issn><issn>1558-9331</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>8G5</sourceid><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>AZQEC</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><sourceid>GNUQQ</sourceid><sourceid>GUQSH</sourceid><sourceid>M2O</sourceid><recordid>eNp9kU1LAzEQhoMoWD9-gCcXxGM0M9nsJieR4hdUKmjBW8imSYmsu5q0aP-9KSviRU9hyPMkM-8QcgTsDBirzxNAXVaUAVJkXFC1RUYghKSKc9gmI8YYpwzheZfspfSSS8lRjMjFwyoGH6xZhr4rel8gve-73th1u2jX1sW-TcUshW5RTML7KsyL8RSLq89lNHajHJAdb9rkDr_PfTK7vnoa39LJ9OZufDmhHiUqCsBU48BJRFliwytupPJVNXeWNY7zplK2hnnFGysZ-toKLIVxjQWF1hvO98nJ8O5b7N9XLi31S7-KXf5SA8sjCl7WMlOn35RJ1rQ-ms6GpN9ieDVxrbFCVguoMlcP3Edo3frnHpjehKmHMHUOU2_C1EpfTsePIFBlEwczZalbuPi7jz_sLB0Pkje9NouYW5o9IoMyr6HEEuS_RAbyaF9F-YlT</recordid><startdate>201208</startdate><enddate>201208</enddate><creator>Compton, David L</creator><creator>Eller, Fred J</creator><creator>Laszlo, Joseph A</creator><creator>Evans, Kervin O</creator><general>Springer-Verlag</general><general>Springer</general><general>Springer Nature B.V</general><scope>FBQ</scope><scope>IQODW</scope><scope>3V.</scope><scope>4T-</scope><scope>7X2</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>88I</scope><scope>8AO</scope><scope>8FE</scope><scope>8FG</scope><scope>8FH</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>8G5</scope><scope>ABJCF</scope><scope>ABUWG</scope><scope>AEUYN</scope><scope>AFKRA</scope><scope>ATCPS</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>BHPHI</scope><scope>BKSAR</scope><scope>CCPQU</scope><scope>D1I</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>GUQSH</scope><scope>HCIFZ</scope><scope>K9.</scope><scope>KB.</scope><scope>M0K</scope><scope>M0S</scope><scope>M1P</scope><scope>M2O</scope><scope>M2P</scope><scope>MBDVC</scope><scope>PCBAR</scope><scope>PDBOC</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>Q9U</scope></search><sort><creationdate>201208</creationdate><title>Purification of 2-Monoacylglycerols Using Liquid CO2 Extraction</title><author>Compton, David L ; Eller, Fred J ; Laszlo, Joseph A ; Evans, Kervin O</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-f2829-1109be1e822842b363a89f66dec0be33b69c71d63bc802f7c5245aebc192cfa33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>2‐Monoacylglycerol</topic><topic>Acyl migration</topic><topic>Agriculture</topic><topic>Biological and medical sciences</topic><topic>Biomaterials</topic><topic>Biotechnology</topic><topic>Carbon dioxide</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chromatography</topic><topic>Esters</topic><topic>ethanolysis</topic><topic>Fat industries</topic><topic>Fatty acids</topic><topic>Food engineering</topic><topic>Food industries</topic><topic>Food Science</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>General aspects</topic><topic>Industrial Chemistry/Chemical Engineering</topic><topic>Lipids</topic><topic>Liquid CO2</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>nuclear magnetic resonance spectroscopy</topic><topic>Original Paper</topic><topic>Structured lipids</topic><topic>supercritical fluid chromatography</topic><topic>temperature</topic><topic>Thermodynamics</topic><topic>triolein</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Compton, David L</creatorcontrib><creatorcontrib>Eller, Fred J</creatorcontrib><creatorcontrib>Laszlo, Joseph A</creatorcontrib><creatorcontrib>Evans, Kervin O</creatorcontrib><collection>AGRIS</collection><collection>Pascal-Francis</collection><collection>ProQuest Central (Corporate)</collection><collection>Docstoc</collection><collection>Agricultural Science Collection</collection><collection>Health & Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Medical Database (Alumni Edition)</collection><collection>Science Database (Alumni Edition)</collection><collection>ProQuest Pharma Collection</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</collection><collection>ProQuest Natural Science Collection</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>Research Library (Alumni Edition)</collection><collection>Materials Science & Engineering Collection</collection><collection>ProQuest Central (Alumni Edition)</collection><collection>ProQuest One Sustainability</collection><collection>ProQuest Central UK/Ireland</collection><collection>Agricultural & Environmental Science Collection</collection><collection>ProQuest Central Essentials</collection><collection>ProQuest Central</collection><collection>Technology Collection</collection><collection>Natural Science Collection</collection><collection>Earth, Atmospheric & Aquatic Science Collection</collection><collection>ProQuest One Community College</collection><collection>ProQuest Materials Science Collection</collection><collection>ProQuest Central Korea</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Central Student</collection><collection>Research Library Prep</collection><collection>SciTech Premium Collection</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Materials Science Database</collection><collection>Agricultural Science Database</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>Medical Database</collection><collection>Research Library</collection><collection>Science Database</collection><collection>Research Library (Corporate)</collection><collection>Earth, Atmospheric & Aquatic Science Database</collection><collection>Materials Science Collection</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central Basic</collection><jtitle>Journal of the American Oil Chemists' Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Compton, David L</au><au>Eller, Fred J</au><au>Laszlo, Joseph A</au><au>Evans, Kervin O</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Purification of 2-Monoacylglycerols Using Liquid CO2 Extraction</atitle><jtitle>Journal of the American Oil Chemists' Society</jtitle><stitle>J Am Oil Chem Soc</stitle><date>2012-08</date><risdate>2012</risdate><volume>89</volume><issue>8</issue><spage>1529</spage><epage>1536</epage><pages>1529-1536</pages><issn>0003-021X</issn><eissn>1558-9331</eissn><abstract>The fatty acid moiety of 2-monoacyl-sn-glycerol (2-MAG) undergoes spontaneous acyl migration to the sn-1(3) position, resulting in a thermodynamic equilibrium of approximately 1:9 of 2-MAG to 1(3)-monoacyl-sn-glycerol (1-MAG). Spontaneous acyl migration is an impediment to synthesizing and isolating specific 2-MAG for use as intermediates in the synthesis of structured triacylglycerols. 2-Monooleoyl-sn-glycerol was synthesized by the enzymatic ethanolysis of triolein and isolated by liquid CO2 extraction. The resultant MAG, diacylglycerol, and fatty acid ethyl esters were quantified by 1H NMR and supercritical fluid chromatography. The low polarity of the CO2 and mild extraction temperature (25 °C) resulted in very low spontaneous acyl migration rates, allowing the MAG to be isolated in 80% yield and in a very high 2-MAG:1-MAG ratios of ≥93 mol%.</abstract><cop>Berlin/Heidelberg</cop><pub>Springer-Verlag</pub><doi>10.1007/s11746-012-2035-9</doi><tpages>8</tpages></addata></record> |
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| subjects | 2‐Monoacylglycerol Acyl migration Agriculture Biological and medical sciences Biomaterials Biotechnology Carbon dioxide Chemistry Chemistry and Materials Science Chromatography Esters ethanolysis Fat industries Fatty acids Food engineering Food industries Food Science Fundamental and applied biological sciences. Psychology General aspects Industrial Chemistry/Chemical Engineering Lipids Liquid CO2 NMR Nuclear magnetic resonance nuclear magnetic resonance spectroscopy Original Paper Structured lipids supercritical fluid chromatography temperature Thermodynamics triolein |
| title | Purification of 2-Monoacylglycerols Using Liquid CO2 Extraction |
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