Large-scale preparation of (9Z,12E)-[1- 13C]-octadeca-9,12-dienoic acid, (9Z,12Z,15E)-[1- 13C]-octadeca-9,12,15-trienoic acid and their [1- 13C] all- cis isomers
Several grams of labelled trans linoleic and linolenic acids with high chemical and isomeric purities (>97%) have been prepared for human metabolism studies. A total of 12.5 g of (9Z,12E)-[1- 13C]-octadeca-9,12-dienoic acid and 6.3 g of (9Z,12Z,15E)-[1- 13C]-octadeca-9,12,15-trienoic acid were ob...
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| Veröffentlicht in: | Chemistry and physics of lipids 2000-06, Vol.106 (1), p.65-78 |
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| container_title | Chemistry and physics of lipids |
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| creator | Loreau, O Maret, A Poullain, D Chardigny, J.M Sébédio, J.L Beaufrère, B Noël, J.P |
| description | Several grams of labelled
trans linoleic and linolenic acids with high chemical and isomeric purities (>97%) have been prepared for human metabolism studies. A total of 12.5 g of (9Z,12E)-[1-
13C]-octadeca-9,12-dienoic acid and 6.3 g of (9Z,12Z,15E)-[1-
13C]-octadeca-9,12,15-trienoic acid were obtained in, respectively, seven steps (7.8% overall yield) and 11 steps (7% overall yield) from 7-bromo-heptan-1-ol. The
trans bromo precursors used for the labelling were synthesised by using copper-catalysed couplings. The
trans fatty acids were then obtained via the nitrile derivatives. A total of 23.5 g of (9Z,12Z)-[1-
13C]-octadeca-9,12-dienoic acid and 10.4 g of (9Z,12Z,15Z)-[1-
13C]-octadeca-9,12,15-trienoic acid were prepared in five steps in, respectively, 32 and 18% overall yield. Large quantities of bromo and chloro precursors were synthesised from the commercially available acid according to Barton's procedure. In all cases, the main impurities (>0.5%) of each labelled fatty acid have been characterised. |
| doi_str_mv | 10.1016/S0009-3084(00)00137-7 |
| format | Article |
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trans linoleic and linolenic acids with high chemical and isomeric purities (>97%) have been prepared for human metabolism studies. A total of 12.5 g of (9Z,12E)-[1-
13C]-octadeca-9,12-dienoic acid and 6.3 g of (9Z,12Z,15E)-[1-
13C]-octadeca-9,12,15-trienoic acid were obtained in, respectively, seven steps (7.8% overall yield) and 11 steps (7% overall yield) from 7-bromo-heptan-1-ol. The
trans bromo precursors used for the labelling were synthesised by using copper-catalysed couplings. The
trans fatty acids were then obtained via the nitrile derivatives. A total of 23.5 g of (9Z,12Z)-[1-
13C]-octadeca-9,12-dienoic acid and 10.4 g of (9Z,12Z,15Z)-[1-
13C]-octadeca-9,12,15-trienoic acid were prepared in five steps in, respectively, 32 and 18% overall yield. Large quantities of bromo and chloro precursors were synthesised from the commercially available acid according to Barton's procedure. In all cases, the main impurities (>0.5%) of each labelled fatty acid have been characterised.</description><identifier>ISSN: 0009-3084</identifier><identifier>EISSN: 1873-2941</identifier><identifier>DOI: 10.1016/S0009-3084(00)00137-7</identifier><identifier>PMID: 10878236</identifier><language>eng</language><publisher>Ireland: Elsevier Ireland Ltd</publisher><subject>alpha-Linolenic Acid - chemical synthesis ; alpha-Linolenic Acid - chemistry ; Carbon 13 ; Carbon Isotopes ; cis ; Gas Chromatography-Mass Spectrometry ; Humans ; Labelling ; Linoleic ; Linoleic Acid - chemical synthesis ; Linoleic Acid - chemistry ; Linolenic ; Magnetic Resonance Spectroscopy ; Methods ; Stereoisomerism ; trans</subject><ispartof>Chemistry and physics of lipids, 2000-06, Vol.106 (1), p.65-78</ispartof><rights>2000 Elsevier Science Ireland Ltd</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c361t-b1d9fc4af13e394a5d79d300ddf20a29da82a3a7f2cc5a6a93707bcb7f10f3733</citedby><cites>FETCH-LOGICAL-c361t-b1d9fc4af13e394a5d79d300ddf20a29da82a3a7f2cc5a6a93707bcb7f10f3733</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0009308400001377$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3536,27903,27904,65309</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/10878236$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Loreau, O</creatorcontrib><creatorcontrib>Maret, A</creatorcontrib><creatorcontrib>Poullain, D</creatorcontrib><creatorcontrib>Chardigny, J.M</creatorcontrib><creatorcontrib>Sébédio, J.L</creatorcontrib><creatorcontrib>Beaufrère, B</creatorcontrib><creatorcontrib>Noël, J.P</creatorcontrib><title>Large-scale preparation of (9Z,12E)-[1- 13C]-octadeca-9,12-dienoic acid, (9Z,12Z,15E)-[1- 13C]-octadeca-9,12,15-trienoic acid and their [1- 13C] all- cis isomers</title><title>Chemistry and physics of lipids</title><addtitle>Chem Phys Lipids</addtitle><description>Several grams of labelled
trans linoleic and linolenic acids with high chemical and isomeric purities (>97%) have been prepared for human metabolism studies. A total of 12.5 g of (9Z,12E)-[1-
13C]-octadeca-9,12-dienoic acid and 6.3 g of (9Z,12Z,15E)-[1-
13C]-octadeca-9,12,15-trienoic acid were obtained in, respectively, seven steps (7.8% overall yield) and 11 steps (7% overall yield) from 7-bromo-heptan-1-ol. The
trans bromo precursors used for the labelling were synthesised by using copper-catalysed couplings. The
trans fatty acids were then obtained via the nitrile derivatives. A total of 23.5 g of (9Z,12Z)-[1-
13C]-octadeca-9,12-dienoic acid and 10.4 g of (9Z,12Z,15Z)-[1-
13C]-octadeca-9,12,15-trienoic acid were prepared in five steps in, respectively, 32 and 18% overall yield. Large quantities of bromo and chloro precursors were synthesised from the commercially available acid according to Barton's procedure. In all cases, the main impurities (>0.5%) of each labelled fatty acid have been characterised.</description><subject>alpha-Linolenic Acid - chemical synthesis</subject><subject>alpha-Linolenic Acid - chemistry</subject><subject>Carbon 13</subject><subject>Carbon Isotopes</subject><subject>cis</subject><subject>Gas Chromatography-Mass Spectrometry</subject><subject>Humans</subject><subject>Labelling</subject><subject>Linoleic</subject><subject>Linoleic Acid - chemical synthesis</subject><subject>Linoleic Acid - chemistry</subject><subject>Linolenic</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Methods</subject><subject>Stereoisomerism</subject><subject>trans</subject><issn>0009-3084</issn><issn>1873-2941</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2000</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkdFqVDEQhoNY7Fp9BCVX0kKjMyfnbE6uRJaqhQUv1BtFwmwy0cjZPdvkrODj-Kam3bX0pngRhjDfP8P8vxDPEF4i4PzVRwCwSkPfngKcAaA2yjwQM-yNVo1t8aGY3SLH4nEpP-sXug4fiWOE3vSNns_EnyXl76yKp4HlNvOWMk1p3MgxylP75RybizP1FZVEvfimRj9RYE_K1oYKiTdj8pJ8CucHur7uXkXtqSnfUUnaBDn94JTlP4WkYVDSpyJTGdecyxNxFGko_PRQT8TntxefFu_V8sO7y8WbpfJ6jpNaYbDRtxRRs7YtdcHYoAFCiA1QYwP1DWkysfG-ozlZbcCs_MpEhKiN1ifixX7uNo9XOy6TW6fieRhow-OuOIPVsA7bCnZ70OexlMzRbXNaU_7tENx1Nu4mG3dtvANwN9k4U3XPDwt2qzWHO6p9GBV4vQe4nvkrcXbFV7M8h5TZTy6M6T8r_gLayZee</recordid><startdate>20000601</startdate><enddate>20000601</enddate><creator>Loreau, O</creator><creator>Maret, A</creator><creator>Poullain, D</creator><creator>Chardigny, J.M</creator><creator>Sébédio, J.L</creator><creator>Beaufrère, B</creator><creator>Noël, J.P</creator><general>Elsevier Ireland Ltd</general><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>20000601</creationdate><title>Large-scale preparation of (9Z,12E)-[1- 13C]-octadeca-9,12-dienoic acid, (9Z,12Z,15E)-[1- 13C]-octadeca-9,12,15-trienoic acid and their [1- 13C] all- cis isomers</title><author>Loreau, O ; Maret, A ; Poullain, D ; Chardigny, J.M ; Sébédio, J.L ; Beaufrère, B ; Noël, J.P</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c361t-b1d9fc4af13e394a5d79d300ddf20a29da82a3a7f2cc5a6a93707bcb7f10f3733</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2000</creationdate><topic>alpha-Linolenic Acid - chemical synthesis</topic><topic>alpha-Linolenic Acid - chemistry</topic><topic>Carbon 13</topic><topic>Carbon Isotopes</topic><topic>cis</topic><topic>Gas Chromatography-Mass Spectrometry</topic><topic>Humans</topic><topic>Labelling</topic><topic>Linoleic</topic><topic>Linoleic Acid - chemical synthesis</topic><topic>Linoleic Acid - chemistry</topic><topic>Linolenic</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Methods</topic><topic>Stereoisomerism</topic><topic>trans</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Loreau, O</creatorcontrib><creatorcontrib>Maret, A</creatorcontrib><creatorcontrib>Poullain, D</creatorcontrib><creatorcontrib>Chardigny, J.M</creatorcontrib><creatorcontrib>Sébédio, J.L</creatorcontrib><creatorcontrib>Beaufrère, B</creatorcontrib><creatorcontrib>Noël, J.P</creatorcontrib><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>Chemistry and physics of lipids</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Loreau, O</au><au>Maret, A</au><au>Poullain, D</au><au>Chardigny, J.M</au><au>Sébédio, J.L</au><au>Beaufrère, B</au><au>Noël, J.P</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Large-scale preparation of (9Z,12E)-[1- 13C]-octadeca-9,12-dienoic acid, (9Z,12Z,15E)-[1- 13C]-octadeca-9,12,15-trienoic acid and their [1- 13C] all- cis isomers</atitle><jtitle>Chemistry and physics of lipids</jtitle><addtitle>Chem Phys Lipids</addtitle><date>2000-06-01</date><risdate>2000</risdate><volume>106</volume><issue>1</issue><spage>65</spage><epage>78</epage><pages>65-78</pages><issn>0009-3084</issn><eissn>1873-2941</eissn><abstract>Several grams of labelled
trans linoleic and linolenic acids with high chemical and isomeric purities (>97%) have been prepared for human metabolism studies. A total of 12.5 g of (9Z,12E)-[1-
13C]-octadeca-9,12-dienoic acid and 6.3 g of (9Z,12Z,15E)-[1-
13C]-octadeca-9,12,15-trienoic acid were obtained in, respectively, seven steps (7.8% overall yield) and 11 steps (7% overall yield) from 7-bromo-heptan-1-ol. The
trans bromo precursors used for the labelling were synthesised by using copper-catalysed couplings. The
trans fatty acids were then obtained via the nitrile derivatives. A total of 23.5 g of (9Z,12Z)-[1-
13C]-octadeca-9,12-dienoic acid and 10.4 g of (9Z,12Z,15Z)-[1-
13C]-octadeca-9,12,15-trienoic acid were prepared in five steps in, respectively, 32 and 18% overall yield. Large quantities of bromo and chloro precursors were synthesised from the commercially available acid according to Barton's procedure. In all cases, the main impurities (>0.5%) of each labelled fatty acid have been characterised.</abstract><cop>Ireland</cop><pub>Elsevier Ireland Ltd</pub><pmid>10878236</pmid><doi>10.1016/S0009-3084(00)00137-7</doi><tpages>14</tpages></addata></record> |
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| ispartof | Chemistry and physics of lipids, 2000-06, Vol.106 (1), p.65-78 |
| issn | 0009-3084 1873-2941 |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | alpha-Linolenic Acid - chemical synthesis alpha-Linolenic Acid - chemistry Carbon 13 Carbon Isotopes cis Gas Chromatography-Mass Spectrometry Humans Labelling Linoleic Linoleic Acid - chemical synthesis Linoleic Acid - chemistry Linolenic Magnetic Resonance Spectroscopy Methods Stereoisomerism trans |
| title | Large-scale preparation of (9Z,12E)-[1- 13C]-octadeca-9,12-dienoic acid, (9Z,12Z,15E)-[1- 13C]-octadeca-9,12,15-trienoic acid and their [1- 13C] all- cis isomers |
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