Synthesis of (9Z, 12E)-, (9E, 12Z)-[1-<sup>14</sup>C]-linoleic acid, (9Z, 12Z, 15E)-, (9E, 12Z, 15Z)-[1-<sup>14</sup>C]-linolenic acid and (5Z, 8Z, 11Z, 14E)-[1-<sup>14</sup>C]-arachidonic acid
Trans polyunsaturated fatty acids are produced in vegetable oils during heat treatment (240-250 °C).ln order to study the metabolic pathway of 9c, 12t and 9t, 12c linoleic acid and 9c, 12c, 15t and 9t, 12c, 15c linolenic acid, these products were prepared labelled with carbon 14 in the carboxylic p...
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Consejo Superior de Investigaciones Científicas
1996-04-01
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| Series: | Grasas y Aceites |
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| Online Access: | https://grasasyaceites.revistas.csic.es/index.php/grasasyaceites/article/view/848 |
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| author | Thierry Enard Jean Michel Vatéle Olivier Berdeaux Didier Poillain Jean Pierre Nöel |
| author_facet | Thierry Enard Jean Michel Vatéle Olivier Berdeaux Didier Poillain Jean Pierre Nöel |
| author_sort | Thierry Enard |
| collection | DOAJ |
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Trans polyunsaturated fatty acids are produced in vegetable oils during heat treatment (240-250 °C).ln order to study the metabolic pathway of 9c, 12t and 9t, 12c linoleic acid and 9c, 12c, 15t and 9t, 12c, 15c linolenic acid, these products were prepared labelled with carbon 14 in the carboxylic position. 5c, 8c, 11c, 14t-Arachidonic acid was also labelled on the carboxylic position with carbon 14 in order to study its physiological effects. To introduce the labelling (E)-bromo precursors with a 17 carbons chain or a 19 carbon chain were needed. The different syntheses were done by elongation steps and creation of cis double bonds via highly stereospecific Wittig reactions. The radioactive carbon atom was introduced from [14C]-potassium cyanide. The final radioactive fatty acids had a specific activity greater than 50 mCi/mmol and a radioactive purity better than 99 % for linoleic and linolenic and better than 98.6 % for arachidonic acid.
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| format | Article |
| id | doaj-art-169b5483c31d4b87ad5e5eb8ac0167f9 |
| institution | DOAJ |
| issn | 0017-3495 1988-4214 |
| language | English |
| publishDate | 1996-04-01 |
| publisher | Consejo Superior de Investigaciones Científicas |
| record_format | Article |
| series | Grasas y Aceites |
| spelling | doaj-art-169b5483c31d4b87ad5e5eb8ac0167f92025-08-20T03:10:59ZengConsejo Superior de Investigaciones CientíficasGrasas y Aceites0017-34951988-42141996-04-01471-210.3989/gya.1996.v47.i1-2.848832Synthesis of (9Z, 12E)-, (9E, 12Z)-[1-<sup>14</sup>C]-linoleic acid, (9Z, 12Z, 15E)-, (9E, 12Z, 15Z)-[1-<sup>14</sup>C]-linolenic acid and (5Z, 8Z, 11Z, 14E)-[1-<sup>14</sup>C]-arachidonic acidThierry Enard0Jean Michel Vatéle1Olivier Berdeaux2Didier Poillain3Jean Pierre Nöel4Laboratoire de Chimie Organique 1, associe au CNRS, Université Claude BernardLaboratoire de Chimie Organique 1, associe au CNRS, Université Claude BernardINRA, Unite de Nutrition LipidiqueCEA/Saclay, Service des Molécules MarquéesCEA/Saclay, Service des Molécules Marquées Trans polyunsaturated fatty acids are produced in vegetable oils during heat treatment (240-250 °C).ln order to study the metabolic pathway of 9c, 12t and 9t, 12c linoleic acid and 9c, 12c, 15t and 9t, 12c, 15c linolenic acid, these products were prepared labelled with carbon 14 in the carboxylic position. 5c, 8c, 11c, 14t-Arachidonic acid was also labelled on the carboxylic position with carbon 14 in order to study its physiological effects. To introduce the labelling (E)-bromo precursors with a 17 carbons chain or a 19 carbon chain were needed. The different syntheses were done by elongation steps and creation of cis double bonds via highly stereospecific Wittig reactions. The radioactive carbon atom was introduced from [14C]-potassium cyanide. The final radioactive fatty acids had a specific activity greater than 50 mCi/mmol and a radioactive purity better than 99 % for linoleic and linolenic and better than 98.6 % for arachidonic acid. https://grasasyaceites.revistas.csic.es/index.php/grasasyaceites/article/view/848[14C]-fatty acidstrans-arachidonic acidtrans-linoleic acidtrans-linolenic acidWittig reaction |
| spellingShingle | Thierry Enard Jean Michel Vatéle Olivier Berdeaux Didier Poillain Jean Pierre Nöel Synthesis of (9Z, 12E)-, (9E, 12Z)-[1-<sup>14</sup>C]-linoleic acid, (9Z, 12Z, 15E)-, (9E, 12Z, 15Z)-[1-<sup>14</sup>C]-linolenic acid and (5Z, 8Z, 11Z, 14E)-[1-<sup>14</sup>C]-arachidonic acid Grasas y Aceites [14C]-fatty acids trans-arachidonic acid trans-linoleic acid trans-linolenic acid Wittig reaction |
| title | Synthesis of (9Z, 12E)-, (9E, 12Z)-[1-<sup>14</sup>C]-linoleic acid, (9Z, 12Z, 15E)-, (9E, 12Z, 15Z)-[1-<sup>14</sup>C]-linolenic acid and (5Z, 8Z, 11Z, 14E)-[1-<sup>14</sup>C]-arachidonic acid |
| title_full | Synthesis of (9Z, 12E)-, (9E, 12Z)-[1-<sup>14</sup>C]-linoleic acid, (9Z, 12Z, 15E)-, (9E, 12Z, 15Z)-[1-<sup>14</sup>C]-linolenic acid and (5Z, 8Z, 11Z, 14E)-[1-<sup>14</sup>C]-arachidonic acid |
| title_fullStr | Synthesis of (9Z, 12E)-, (9E, 12Z)-[1-<sup>14</sup>C]-linoleic acid, (9Z, 12Z, 15E)-, (9E, 12Z, 15Z)-[1-<sup>14</sup>C]-linolenic acid and (5Z, 8Z, 11Z, 14E)-[1-<sup>14</sup>C]-arachidonic acid |
| title_full_unstemmed | Synthesis of (9Z, 12E)-, (9E, 12Z)-[1-<sup>14</sup>C]-linoleic acid, (9Z, 12Z, 15E)-, (9E, 12Z, 15Z)-[1-<sup>14</sup>C]-linolenic acid and (5Z, 8Z, 11Z, 14E)-[1-<sup>14</sup>C]-arachidonic acid |
| title_short | Synthesis of (9Z, 12E)-, (9E, 12Z)-[1-<sup>14</sup>C]-linoleic acid, (9Z, 12Z, 15E)-, (9E, 12Z, 15Z)-[1-<sup>14</sup>C]-linolenic acid and (5Z, 8Z, 11Z, 14E)-[1-<sup>14</sup>C]-arachidonic acid |
| title_sort | synthesis of 9z 12e 9e 12z 1 sup 14 sup c linoleic acid 9z 12z 15e 9e 12z 15z 1 sup 14 sup c linolenic acid and 5z 8z 11z 14e 1 sup 14 sup c arachidonic acid |
| topic | [14C]-fatty acids trans-arachidonic acid trans-linoleic acid trans-linolenic acid Wittig reaction |
| url | https://grasasyaceites.revistas.csic.es/index.php/grasasyaceites/article/view/848 |
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