Occurrence of conjugated linolenic acids in purified soybean oil
A high‐performance liquid chromatographic (HPLC) method is described for the determination of conjugated linoleic acids (CLA) and conjugated linolenic acids (CLN). Methyl esters prepared from purified lipid fractions of soybean oil were analyzed using an HPLC system equipped with photodiode‐array de...
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| Veröffentlicht in: | Journal of the American Oil Chemists' Society 2007, Vol.84 (1), p.23-29 |
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| creator | Kinami, T Horii, N Narayan, B Arato, S Hosokawa, M Miyashita, K Negishi, H Ikuina, J Noda, R Shirasawa, S |
| description | A high‐performance liquid chromatographic (HPLC) method is described for the determination of conjugated linoleic acids (CLA) and conjugated linolenic acids (CLN). Methyl esters prepared from purified lipid fractions of soybean oil were analyzed using an HPLC system equipped with photodiode‐array detector to detect peaks having maximum absorption around 233 and 275 nm. These peaks were concentrated by AgNO3‐silicic acid column chromatography and reversed‐phase HPLC. The structural analysis, of dimethyloxazoline (DMOX) derivatized methyl esters, using gas chromatography–mass spectrometry (GC–MS) showed the occurrence of 9,11‐ and 10,12‐CLA and 8,10,13‐, 8,10,12‐, and 9,11,13‐CLN. The comparison of these conjugated fatty acids with authentic isomers by HPLC revealed the presence of isomeric mixtures of CLA [cis (c),trans(t) or t,c and t,t] and CLN (c,t,t or t,t,c and t,t,t). Traces of 9,11‐ and 10,12‐CLA (c,t or t,c) were found in crude oil. CLN isomers (8,10,12‐18:3 and 9,11,13‐18:3) were found to be forming during the bleaching phase of soybean oil processing. 8,10,13‐CLN and 9,11‐ and 10,12‐CLA (t,t) were only found in soybean oil after the deodorization step. CLN contents in commercial soybean oil varied from 387 to 1,316 mg/kg oil. A decreased level of bleaching earth and temperature resulted in a reduced CLN content. It is possible that CLN would be derived from the linoleate hydroperoxides formed during the processing and storage of soybean oil. |
| doi_str_mv | 10.1007/s11746-006-1005-5 |
| format | Article |
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Methyl esters prepared from purified lipid fractions of soybean oil were analyzed using an HPLC system equipped with photodiode‐array detector to detect peaks having maximum absorption around 233 and 275 nm. These peaks were concentrated by AgNO3‐silicic acid column chromatography and reversed‐phase HPLC. The structural analysis, of dimethyloxazoline (DMOX) derivatized methyl esters, using gas chromatography–mass spectrometry (GC–MS) showed the occurrence of 9,11‐ and 10,12‐CLA and 8,10,13‐, 8,10,12‐, and 9,11,13‐CLN. The comparison of these conjugated fatty acids with authentic isomers by HPLC revealed the presence of isomeric mixtures of CLA [cis (c),trans(t) or t,c and t,t] and CLN (c,t,t or t,t,c and t,t,t). Traces of 9,11‐ and 10,12‐CLA (c,t or t,c) were found in crude oil. CLN isomers (8,10,12‐18:3 and 9,11,13‐18:3) were found to be forming during the bleaching phase of soybean oil processing. 8,10,13‐CLN and 9,11‐ and 10,12‐CLA (t,t) were only found in soybean oil after the deodorization step. CLN contents in commercial soybean oil varied from 387 to 1,316 mg/kg oil. A decreased level of bleaching earth and temperature resulted in a reduced CLN content. It is possible that CLN would be derived from the linoleate hydroperoxides formed during the processing and storage of soybean oil.</description><identifier>ISSN: 0003-021X</identifier><identifier>EISSN: 1558-9331</identifier><identifier>DOI: 10.1007/s11746-006-1005-5</identifier><language>eng</language><publisher>Berlin/Heidelberg: Springer-Verlag</publisher><subject>Biological and medical sciences ; Bleaching ; chemical analysis ; Chromatography ; CLA ; CLN ; conjugated fatty acids ; conjugated linolenic acids ; Crude oil ; Esters ; Fat industries ; Fatty acids ; Food industries ; food processing ; food storage ; Fundamental and applied biological sciences. Psychology ; Gas chromatography ; high performance liquid chromatography ; HPLC ; isomers ; linolenic acid ; Lipid oxidation ; Liquid chromatography ; Mass spectrometry ; photodiode-array detector ; Soybean oil ; Soybeans ; Structural analysis ; Temperature ; Vegetable oils</subject><ispartof>Journal of the American Oil Chemists' Society, 2007, Vol.84 (1), p.23-29</ispartof><rights>2007 American Oil Chemists' Society (AOCS)</rights><rights>2007 INIST-CNRS</rights><rights>Copyright AOCS Press Jan 2007</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4903-58ecd3993fc14fec891c813e9bef4abb943adf7d2359af0585a472992fbbf55c3</citedby><cites>FETCH-LOGICAL-c4903-58ecd3993fc14fec891c813e9bef4abb943adf7d2359af0585a472992fbbf55c3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1007%2Fs11746-006-1005-5$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1007%2Fs11746-006-1005-5$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,4009,27902,27903,27904,45553,45554</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=18483405$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Kinami, T</creatorcontrib><creatorcontrib>Horii, N</creatorcontrib><creatorcontrib>Narayan, B</creatorcontrib><creatorcontrib>Arato, S</creatorcontrib><creatorcontrib>Hosokawa, M</creatorcontrib><creatorcontrib>Miyashita, K</creatorcontrib><creatorcontrib>Negishi, H</creatorcontrib><creatorcontrib>Ikuina, J</creatorcontrib><creatorcontrib>Noda, R</creatorcontrib><creatorcontrib>Shirasawa, S</creatorcontrib><title>Occurrence of conjugated linolenic acids in purified soybean oil</title><title>Journal of the American Oil Chemists' Society</title><description>A high‐performance liquid chromatographic (HPLC) method is described for the determination of conjugated linoleic acids (CLA) and conjugated linolenic acids (CLN). Methyl esters prepared from purified lipid fractions of soybean oil were analyzed using an HPLC system equipped with photodiode‐array detector to detect peaks having maximum absorption around 233 and 275 nm. These peaks were concentrated by AgNO3‐silicic acid column chromatography and reversed‐phase HPLC. The structural analysis, of dimethyloxazoline (DMOX) derivatized methyl esters, using gas chromatography–mass spectrometry (GC–MS) showed the occurrence of 9,11‐ and 10,12‐CLA and 8,10,13‐, 8,10,12‐, and 9,11,13‐CLN. The comparison of these conjugated fatty acids with authentic isomers by HPLC revealed the presence of isomeric mixtures of CLA [cis (c),trans(t) or t,c and t,t] and CLN (c,t,t or t,t,c and t,t,t). Traces of 9,11‐ and 10,12‐CLA (c,t or t,c) were found in crude oil. CLN isomers (8,10,12‐18:3 and 9,11,13‐18:3) were found to be forming during the bleaching phase of soybean oil processing. 8,10,13‐CLN and 9,11‐ and 10,12‐CLA (t,t) were only found in soybean oil after the deodorization step. CLN contents in commercial soybean oil varied from 387 to 1,316 mg/kg oil. A decreased level of bleaching earth and temperature resulted in a reduced CLN content. It is possible that CLN would be derived from the linoleate hydroperoxides formed during the processing and storage of soybean oil.</description><subject>Biological and medical sciences</subject><subject>Bleaching</subject><subject>chemical analysis</subject><subject>Chromatography</subject><subject>CLA</subject><subject>CLN</subject><subject>conjugated fatty acids</subject><subject>conjugated linolenic acids</subject><subject>Crude oil</subject><subject>Esters</subject><subject>Fat industries</subject><subject>Fatty acids</subject><subject>Food industries</subject><subject>food processing</subject><subject>food storage</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Gas chromatography</subject><subject>high performance liquid chromatography</subject><subject>HPLC</subject><subject>isomers</subject><subject>linolenic acid</subject><subject>Lipid oxidation</subject><subject>Liquid chromatography</subject><subject>Mass spectrometry</subject><subject>photodiode-array detector</subject><subject>Soybean oil</subject><subject>Soybeans</subject><subject>Structural analysis</subject><subject>Temperature</subject><subject>Vegetable oils</subject><issn>0003-021X</issn><issn>1558-9331</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</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>eNqFkUtLAzEUhYMoWB8_wJWD4HI0zybZWYovKHRRC-5CJpOUlDGpSQfpvzfDFFy6uhzu-c6FcwG4QfABQcgfM0KcTmsIp3XRrGYnYIIYE7UkBJ2CCYSQ1BCjz3NwkfO2SEEwm4CnpTF9SjYYW0VXmRi2_UbvbVt1PsTOBm8qbXybKx-qXZ-882WX46GxOlTRd1fgzOku2-vjvATrl-eP-Vu9WL6-z2eL2lBZTjNhTUukJM4g6qwREhmBiJWNdVQ3jaREt463mDCpHWSCacqxlNg1jWPMkEtwN-buUvzubd6rbexTKCcV5gwyRAkrJjSaTIo5J-vULvkvnQ4KQTX0pMaeVOlp0EwNzP0xWGejO5d0MD7_gYIKQuHg46Pvx3f28H-wmi3nKwgxKeTtSDodld6kkr5eYYhI4bjk5TO_kkiBMQ</recordid><startdate>2007</startdate><enddate>2007</enddate><creator>Kinami, T</creator><creator>Horii, N</creator><creator>Narayan, B</creator><creator>Arato, S</creator><creator>Hosokawa, M</creator><creator>Miyashita, K</creator><creator>Negishi, H</creator><creator>Ikuina, J</creator><creator>Noda, R</creator><creator>Shirasawa, S</creator><general>Springer-Verlag</general><general>Springer</general><general>Springer Nature B.V</general><scope>FBQ</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</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>2007</creationdate><title>Occurrence of conjugated linolenic acids in purified soybean oil</title><author>Kinami, T ; Horii, N ; Narayan, B ; Arato, S ; Hosokawa, M ; Miyashita, K ; Negishi, H ; Ikuina, J ; Noda, R ; Shirasawa, S</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4903-58ecd3993fc14fec891c813e9bef4abb943adf7d2359af0585a472992fbbf55c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>Biological and medical sciences</topic><topic>Bleaching</topic><topic>chemical analysis</topic><topic>Chromatography</topic><topic>CLA</topic><topic>CLN</topic><topic>conjugated fatty acids</topic><topic>conjugated linolenic acids</topic><topic>Crude oil</topic><topic>Esters</topic><topic>Fat industries</topic><topic>Fatty acids</topic><topic>Food industries</topic><topic>food processing</topic><topic>food storage</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Gas chromatography</topic><topic>high performance liquid chromatography</topic><topic>HPLC</topic><topic>isomers</topic><topic>linolenic acid</topic><topic>Lipid oxidation</topic><topic>Liquid chromatography</topic><topic>Mass spectrometry</topic><topic>photodiode-array detector</topic><topic>Soybean oil</topic><topic>Soybeans</topic><topic>Structural analysis</topic><topic>Temperature</topic><topic>Vegetable oils</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kinami, T</creatorcontrib><creatorcontrib>Horii, N</creatorcontrib><creatorcontrib>Narayan, B</creatorcontrib><creatorcontrib>Arato, S</creatorcontrib><creatorcontrib>Hosokawa, M</creatorcontrib><creatorcontrib>Miyashita, K</creatorcontrib><creatorcontrib>Negishi, H</creatorcontrib><creatorcontrib>Ikuina, J</creatorcontrib><creatorcontrib>Noda, R</creatorcontrib><creatorcontrib>Shirasawa, S</creatorcontrib><collection>AGRIS</collection><collection>Pascal-Francis</collection><collection>CrossRef</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 (ProQuest)</collection><collection>Natural Science Collection (ProQuest)</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>Kinami, T</au><au>Horii, N</au><au>Narayan, B</au><au>Arato, S</au><au>Hosokawa, M</au><au>Miyashita, K</au><au>Negishi, H</au><au>Ikuina, J</au><au>Noda, R</au><au>Shirasawa, S</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Occurrence of conjugated linolenic acids in purified soybean oil</atitle><jtitle>Journal of the American Oil Chemists' Society</jtitle><date>2007</date><risdate>2007</risdate><volume>84</volume><issue>1</issue><spage>23</spage><epage>29</epage><pages>23-29</pages><issn>0003-021X</issn><eissn>1558-9331</eissn><abstract>A high‐performance liquid chromatographic (HPLC) method is described for the determination of conjugated linoleic acids (CLA) and conjugated linolenic acids (CLN). Methyl esters prepared from purified lipid fractions of soybean oil were analyzed using an HPLC system equipped with photodiode‐array detector to detect peaks having maximum absorption around 233 and 275 nm. These peaks were concentrated by AgNO3‐silicic acid column chromatography and reversed‐phase HPLC. The structural analysis, of dimethyloxazoline (DMOX) derivatized methyl esters, using gas chromatography–mass spectrometry (GC–MS) showed the occurrence of 9,11‐ and 10,12‐CLA and 8,10,13‐, 8,10,12‐, and 9,11,13‐CLN. The comparison of these conjugated fatty acids with authentic isomers by HPLC revealed the presence of isomeric mixtures of CLA [cis (c),trans(t) or t,c and t,t] and CLN (c,t,t or t,t,c and t,t,t). Traces of 9,11‐ and 10,12‐CLA (c,t or t,c) were found in crude oil. CLN isomers (8,10,12‐18:3 and 9,11,13‐18:3) were found to be forming during the bleaching phase of soybean oil processing. 8,10,13‐CLN and 9,11‐ and 10,12‐CLA (t,t) were only found in soybean oil after the deodorization step. CLN contents in commercial soybean oil varied from 387 to 1,316 mg/kg oil. A decreased level of bleaching earth and temperature resulted in a reduced CLN content. It is possible that CLN would be derived from the linoleate hydroperoxides formed during the processing and storage of soybean oil.</abstract><cop>Berlin/Heidelberg</cop><pub>Springer-Verlag</pub><doi>10.1007/s11746-006-1005-5</doi><tpages>7</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Biological and medical sciences Bleaching chemical analysis Chromatography CLA CLN conjugated fatty acids conjugated linolenic acids Crude oil Esters Fat industries Fatty acids Food industries food processing food storage Fundamental and applied biological sciences. Psychology Gas chromatography high performance liquid chromatography HPLC isomers linolenic acid Lipid oxidation Liquid chromatography Mass spectrometry photodiode-array detector Soybean oil Soybeans Structural analysis Temperature Vegetable oils |
| title | Occurrence of conjugated linolenic acids in purified soybean oil |
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