https://lipidbank.jp/mediawiki/index.php?action=history&feed=atom&title=LBF18206SC05
LBF18206SC05 - Revision history
2026-06-14T18:33:45Z
Revision history for this page on the wiki
MediaWiki 1.43.0
https://lipidbank.jp/mediawiki/index.php?title=LBF18206SC05&diff=49935&oldid=prev
Editor at 10:28, 1 October 2010
2010-10-01T10:28:17Z
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Editor
https://lipidbank.jp/mediawiki/index.php?title=LBF18206SC05&diff=49934&oldid=prev
Editor at 05:11, 7 September 2010
2010-09-07T05:11:13Z
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Editor
https://lipidbank.jp/mediawiki/index.php?title=LBF18206SC05&diff=49933&oldid=prev
Editor: SysName corrected
2010-06-01T15:04:55Z
<p>SysName corrected</p>
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<td colspan="2" style="background-color: #fff; color: #202122; text-align: center;">Revision as of 00:04, 2 June 2010</td>
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<tr><td class="diff-marker" data-marker="−"></td><td style="color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #ffe49c; vertical-align: top; white-space: pre-wrap;"><div>|SysName=cis-<del style="font-weight: bold; text-decoration: none;">9, </del>cis<del style="font-weight: bold; text-decoration: none;">-12</del>-Octadecadienoic acid</div></td><td class="diff-marker" data-marker="+"></td><td style="color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #a3d3ff; vertical-align: top; white-space: pre-wrap;"><div>|SysName=<ins style="font-weight: bold; text-decoration: none;">(9-</ins>cis<ins style="font-weight: bold; text-decoration: none;">, 12</ins>-cis<ins style="font-weight: bold; text-decoration: none;">) </ins>-Octadecadienoic acid</div></td></tr>
<tr><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Common Name=&&Linoleic acid&&</div></td><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Common Name=&&Linoleic acid&&</div></td></tr>
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Editor
https://lipidbank.jp/mediawiki/index.php?title=LBF18206SC05&diff=49932&oldid=prev
Dbmanager at 06:49, 27 April 2010
2010-04-27T06:49:17Z
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<tr><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Boiling Point=229°C to 230°C at 16mmHg</div></td><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Boiling Point=229°C to 230°C at 16mmHg</div></td></tr>
<tr><td class="diff-marker" data-marker="−"></td><td style="color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #ffe49c; vertical-align: top; white-space: pre-wrap;"><div>|Density=<del style="font-weight: bold; text-decoration: none;">dX</del>^{20}_4 0.9031</div></td><td class="diff-marker" data-marker="+"></td><td style="color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #a3d3ff; vertical-align: top; white-space: pre-wrap;"><div>|Density=<ins style="font-weight: bold; text-decoration: none;">d</ins>^{20}_4 0.9031</div></td></tr>
<tr><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Refractive=1.4711 at 20°C</div></td><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Refractive=1.4711 at 20°C</div></td></tr>
<tr><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Solubility=soluble in acetone, alcohol, ether and petroleum ether.<!--0193-->[[Reference:Matthews_NL:Brode_WR:Brown_JB:,J. Am. Chem. Soc.,1941,63,1064|{{RelationTable/GetFirstAuthor|Reference:Matthews_NL:Brode_WR:Brown_JB:,J. Am. Chem. Soc.,1941,63,1064}}]][[Reference:Nicolaides_N:Laves_F:,J. Am. Chem. Soc.,1958,80,5752|{{RelationTable/GetFirstAuthor|Reference:Nicolaides_N:Laves_F:,J. Am. Chem. Soc.,1958,80,5752}}]]<!--0409--><!--0410--></div></td><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Solubility=soluble in acetone, alcohol, ether and petroleum ether.<!--0193-->[[Reference:Matthews_NL:Brode_WR:Brown_JB:,J. Am. Chem. Soc.,1941,63,1064|{{RelationTable/GetFirstAuthor|Reference:Matthews_NL:Brode_WR:Brown_JB:,J. Am. Chem. Soc.,1941,63,1064}}]][[Reference:Nicolaides_N:Laves_F:,J. Am. Chem. Soc.,1958,80,5752|{{RelationTable/GetFirstAuthor|Reference:Nicolaides_N:Laves_F:,J. Am. Chem. Soc.,1958,80,5752}}]]<!--0409--><!--0410--></div></td></tr>
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Dbmanager
https://lipidbank.jp/mediawiki/index.php?title=LBF18206SC05&diff=49931&oldid=prev
Editor at 21:00, 14 April 2010
2010-04-14T21:00:00Z
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<td colspan="2" style="background-color: #fff; color: #202122; text-align: center;">Revision as of 06:00, 15 April 2010</td>
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<tr><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|SysName=cis-9, cis-12-Octadecadienoic acid</div></td><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|SysName=cis-9, cis-12-Octadecadienoic acid</div></td></tr>
<tr><td class="diff-marker" data-marker="−"></td><td style="color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #ffe49c; vertical-align: top; white-space: pre-wrap;"><div>|Common Name=&&Linoleic <del style="font-weight: bold; text-decoration: none;">acid&&cis-9, cis-12-Octadecadienoic </del>acid&&</div></td><td class="diff-marker" data-marker="+"></td><td style="color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #a3d3ff; vertical-align: top; white-space: pre-wrap;"><div>|Common Name=&&Linoleic acid&&</div></td></tr>
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Editor
https://lipidbank.jp/mediawiki/index.php?title=LBF18206SC05&diff=49930&oldid=prev
Editor at 10:00, 25 February 2010
2010-02-25T10:00:10Z
<p></p>
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<td colspan="2" style="background-color: #fff; color: #202122; text-align: center;">Revision as of 19:00, 25 February 2010</td>
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<tr><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Melting Point=-5°C</div></td><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Melting Point=-5°C</div></td></tr>
<tr><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Boiling Point=229°C to 230°C at 16mmHg</div></td><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Boiling Point=229°C to 230°C at 16mmHg</div></td></tr>
<tr><td class="diff-marker" data-marker="−"></td><td style="color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #ffe49c; vertical-align: top; white-space: pre-wrap;"><div>|Density=dX^<del style="font-weight: bold; text-decoration: none;">20_4 </del> 0.9031</div></td><td class="diff-marker" data-marker="+"></td><td style="color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #a3d3ff; vertical-align: top; white-space: pre-wrap;"><div>|Density=dX^<ins style="font-weight: bold; text-decoration: none;">{20}_4 </ins> 0.9031</div></td></tr>
<tr><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Refractive=1.4711 at 20°C</div></td><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Refractive=1.4711 at 20°C</div></td></tr>
<tr><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Solubility=soluble in acetone, alcohol, ether and petroleum ether.<!--0193-->[[Reference:Matthews_NL:Brode_WR:Brown_JB:,J. Am. Chem. Soc.,1941,63,1064|{{RelationTable/GetFirstAuthor|Reference:Matthews_NL:Brode_WR:Brown_JB:,J. Am. Chem. Soc.,1941,63,1064}}]][[Reference:Nicolaides_N:Laves_F:,J. Am. Chem. Soc.,1958,80,5752|{{RelationTable/GetFirstAuthor|Reference:Nicolaides_N:Laves_F:,J. Am. Chem. Soc.,1958,80,5752}}]]<!--0409--><!--0410--></div></td><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Solubility=soluble in acetone, alcohol, ether and petroleum ether.<!--0193-->[[Reference:Matthews_NL:Brode_WR:Brown_JB:,J. Am. Chem. Soc.,1941,63,1064|{{RelationTable/GetFirstAuthor|Reference:Matthews_NL:Brode_WR:Brown_JB:,J. Am. Chem. Soc.,1941,63,1064}}]][[Reference:Nicolaides_N:Laves_F:,J. Am. Chem. Soc.,1958,80,5752|{{RelationTable/GetFirstAuthor|Reference:Nicolaides_N:Laves_F:,J. Am. Chem. Soc.,1958,80,5752}}]]<!--0409--><!--0410--></div></td></tr>
</table>
Editor
https://lipidbank.jp/mediawiki/index.php?title=LBF18206SC05&diff=49929&oldid=prev
Editor at 14:00, 19 February 2010
2010-02-19T14:00:10Z
<p></p>
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<td colspan="2" style="background-color: #fff; color: #202122; text-align: center;">← Older revision</td>
<td colspan="2" style="background-color: #fff; color: #202122; text-align: center;">Revision as of 23:00, 19 February 2010</td>
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<tr><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Source=Constituent of the essential fatty acids (vitamin F) and of various microorganisms; oils of cottonseed, soybean, peanut, corn, sunflower and poppy seed.</div></td><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Source=Constituent of the essential fatty acids (vitamin F) and of various microorganisms; oils of cottonseed, soybean, peanut, corn, sunflower and poppy seed.</div></td></tr>
<tr><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Chemical Synthesis=</div></td><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Chemical Synthesis=</div></td></tr>
<tr><td class="diff-marker" data-marker="−"></td><td style="color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #ffe49c; vertical-align: top; white-space: pre-wrap;"><div>|Metabolism=Linoleic acid (18:2n-6) is synthesized from oleic acid (18:1n-9) by desaturation of <del style="font-weight: bold; text-decoration: none;">Delta12</del>-desaturase, and alpha-linolenic acid (18:3n-3) is formed from linoleic acid by desaturation reaction of <del style="font-weight: bold; text-decoration: none;">Delta15</del>-desaturase. Since both <del style="font-weight: bold; text-decoration: none;">Delta12</del>- and 15-desaturases are present in plant cells but not in animal cells, linoleic and alpha-linolenic acid are not biosynthesized in animal cells in vivo. When ingested by animals, linoleic acid is desaturated, elongated to form gamma-linolenic acid (18:3n-6), dihomo-gamma-linolenic acid (20:3n-6), arachidonic acid (20:4n-6) and adrenic acid (22:4n-6). Docosapentaenoic acid (22:5n-6) is synthesized from adrenic acid in significant amounts only under conditions of prolonged n-3 fatty acid deficiency., No interconversion between the n-6 and n-3 series in mammals. Nutritionally, it is important to note that different foods contain different proportions of n-6/n-3 and therefore the n-6/n-3 ratio in tissue lipids change significantly depending on the choice of foods.[[Reference:Okuyama_H:Kobayashi_T:Watanabe_S:,Prog. Lipid Res.,1996,35,409|{{RelationTable/GetFirstAuthor|Reference:Okuyama_H:Kobayashi_T:Watanabe_S:,Prog. Lipid Res.,1996,35,409}}]] Although plants synthesize and store linoleic acid and alpha-linolenic acid as well as saturated and monounsaturated fatty acids in grains, the proportions of these fatty acids in different vegetable oils differ greatly. Safflower and sunflower oil contain high levels of linoleate, while perilla and linseed oil are rich in alpha-linolenic acid.</div></td><td class="diff-marker" data-marker="+"></td><td style="color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #a3d3ff; vertical-align: top; white-space: pre-wrap;"><div>|Metabolism=Linoleic acid (18:2n-6) is synthesized from oleic acid (18:1n-9) by desaturation of <ins style="font-weight: bold; text-decoration: none;"> Delta 12</ins>-desaturase, and <ins style="font-weight: bold; text-decoration: none;"> </ins>alpha -linolenic acid (18:3n-3) is formed from linoleic acid by desaturation reaction of <ins style="font-weight: bold; text-decoration: none;"> Delta 15</ins>-desaturase. Since both <ins style="font-weight: bold; text-decoration: none;"> Delta 12</ins>- and 15-desaturases are present in plant cells but not in animal cells, linoleic and <ins style="font-weight: bold; text-decoration: none;"> </ins>alpha -linolenic acid are not biosynthesized in animal cells in vivo. When ingested by animals, linoleic acid is desaturated, elongated to form <ins style="font-weight: bold; text-decoration: none;"> </ins>gamma -linolenic acid (18:3n-6), dihomo- gamma -linolenic acid (20:3n-6), arachidonic acid (20:4n-6) and adrenic acid (22:4n-6). Docosapentaenoic acid (22:5n-6) is synthesized from adrenic acid in significant amounts only under conditions of prolonged n-3 fatty acid deficiency., No interconversion between the n-6 and n-3 series in mammals. Nutritionally, it is important to note that different foods contain different proportions of n-6/n-3 and therefore the n-6/n-3 ratio in tissue lipids change significantly depending on the choice of foods.[[Reference:Okuyama_H:Kobayashi_T:Watanabe_S:,Prog. Lipid Res.,1996,35,409|{{RelationTable/GetFirstAuthor|Reference:Okuyama_H:Kobayashi_T:Watanabe_S:,Prog. Lipid Res.,1996,35,409}}]] Although plants synthesize and store linoleic acid and <ins style="font-weight: bold; text-decoration: none;"> </ins>alpha -linolenic acid as well as saturated and monounsaturated fatty acids in grains, the proportions of these fatty acids in different vegetable oils differ greatly. Safflower and sunflower oil contain high levels of linoleate, while perilla and linseed oil are rich in <ins style="font-weight: bold; text-decoration: none;"> </ins>alpha -linolenic acid.</div></td></tr>
<tr><td class="diff-marker" data-marker="−"></td><td style="color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #ffe49c; vertical-align: top; white-space: pre-wrap;"><div>|Symbol=LA / C18:2n-6 / C18:<del style="font-weight: bold; text-decoration: none;">2omega6</del></div></td><td class="diff-marker" data-marker="+"></td><td style="color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #a3d3ff; vertical-align: top; white-space: pre-wrap;"><div>|Symbol=LA / C18:2n-6 / C18:<ins style="font-weight: bold; text-decoration: none;">2 omega 6</ins></div></td></tr>
<tr><td class="diff-marker" data-marker="−"></td><td style="color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #ffe49c; vertical-align: top; white-space: pre-wrap;"><div>|Biological Activity=There are two groups of essential fatty acids for mammals, the n-6 (or <del style="font-weight: bold; text-decoration: none;">omega6</del>) and the n-3 (or <del style="font-weight: bold; text-decoration: none;">omega3</del>). Linoleic acid (LA) is one of the n-6 essential fatty. Animals deficient in LA show the growth retardation, skin lesions, reproductive failure, fatty liver and polydipsia <!--2009-->[[Reference:Paulsrud_JR:Pensler_L:Whitten_CF:Stewart_S:Holman:RT:,Am. J. Clin. Nutr.,1972,25,897|{{RelationTable/GetFirstAuthor|Reference:Paulsrud_JR:Pensler_L:Whitten_CF:Stewart_S:Holman:RT:,Am. J. Clin. Nutr.,1972,25,897}}]]. Dietary supplementation of either linoleate, gamma-linoleate or arachidonate prevents such symptoms completely. Its physiological functions appear to be mediated mainly through the hormone-like eicosanoids (prostaglandins, leukotriens and thromboxanes et al.) derived from arachidonic acid which is biosynthesized from LA. LA is also shown to be involved in control of the water impermeability of the skin and regulation of cholesterol synthesis and transport.</div></td><td class="diff-marker" data-marker="+"></td><td style="color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #a3d3ff; vertical-align: top; white-space: pre-wrap;"><div>|Biological Activity=There are two groups of essential fatty acids for mammals, the n-6 (or <ins style="font-weight: bold; text-decoration: none;"> omega 6</ins>) and the n-3 (or <ins style="font-weight: bold; text-decoration: none;"> omega 3</ins>). Linoleic acid (LA) is one of the n-6 essential fatty. Animals deficient in LA show the growth retardation, skin lesions, reproductive failure, fatty liver and polydipsia <!--2009-->[[Reference:Paulsrud_JR:Pensler_L:Whitten_CF:Stewart_S:Holman:RT:,Am. J. Clin. Nutr.,1972,25,897|{{RelationTable/GetFirstAuthor|Reference:Paulsrud_JR:Pensler_L:Whitten_CF:Stewart_S:Holman:RT:,Am. J. Clin. Nutr.,1972,25,897}}]]. Dietary supplementation of either linoleate, <ins style="font-weight: bold; text-decoration: none;"> </ins>gamma -linoleate or arachidonate prevents such symptoms completely. Its physiological functions appear to be mediated mainly through the hormone-like eicosanoids (prostaglandins, leukotriens and thromboxanes et al.) derived from arachidonic acid which is biosynthesized from LA. LA is also shown to be involved in control of the water impermeability of the skin and regulation of cholesterol synthesis and transport.</div></td></tr>
<tr><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>}}</div></td><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>}}</div></td></tr>
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<tr><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>{{Lipid/Footer}}</div></td><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>{{Lipid/Footer}}</div></td></tr>
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Editor
https://lipidbank.jp/mediawiki/index.php?title=LBF18206SC05&diff=49928&oldid=prev
Editor at 14:00, 19 February 2010
2010-02-19T14:00:00Z
<p></p>
<table style="background-color: #fff; color: #202122;" data-mw="interface">
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<td colspan="2" style="background-color: #fff; color: #202122; text-align: center;">Revision as of 23:00, 19 February 2010</td>
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<tr><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Melting Point=-5°C</div></td><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Melting Point=-5°C</div></td></tr>
<tr><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Boiling Point=229°C to 230°C at 16mmHg</div></td><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Boiling Point=229°C to 230°C at 16mmHg</div></td></tr>
<tr><td class="diff-marker" data-marker="−"></td><td style="color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #ffe49c; vertical-align: top; white-space: pre-wrap;"><div>|Density=dX<del style="font-weight: bold; text-decoration: none;"><sub>4</sub><sup>20</sup> </del>0.9031</div></td><td class="diff-marker" data-marker="+"></td><td style="color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #a3d3ff; vertical-align: top; white-space: pre-wrap;"><div>|Density=dX<ins style="font-weight: bold; text-decoration: none;">^20_4 </ins>0.9031</div></td></tr>
<tr><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Refractive=1.4711 at 20°C</div></td><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Refractive=1.4711 at 20°C</div></td></tr>
<tr><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Solubility=soluble in acetone, alcohol, ether and petroleum ether.<!--0193-->[[Reference:Matthews_NL:Brode_WR:Brown_JB:,J. Am. Chem. Soc.,1941,63,1064|{{RelationTable/GetFirstAuthor|Reference:Matthews_NL:Brode_WR:Brown_JB:,J. Am. Chem. Soc.,1941,63,1064}}]][[Reference:Nicolaides_N:Laves_F:,J. Am. Chem. Soc.,1958,80,5752|{{RelationTable/GetFirstAuthor|Reference:Nicolaides_N:Laves_F:,J. Am. Chem. Soc.,1958,80,5752}}]]<!--0409--><!--0410--></div></td><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Solubility=soluble in acetone, alcohol, ether and petroleum ether.<!--0193-->[[Reference:Matthews_NL:Brode_WR:Brown_JB:,J. Am. Chem. Soc.,1941,63,1064|{{RelationTable/GetFirstAuthor|Reference:Matthews_NL:Brode_WR:Brown_JB:,J. Am. Chem. Soc.,1941,63,1064}}]][[Reference:Nicolaides_N:Laves_F:,J. Am. Chem. Soc.,1958,80,5752|{{RelationTable/GetFirstAuthor|Reference:Nicolaides_N:Laves_F:,J. Am. Chem. Soc.,1958,80,5752}}]]<!--0409--><!--0410--></div></td></tr>
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<tr><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Source=Constituent of the essential fatty acids (vitamin F) and of various microorganisms; oils of cottonseed, soybean, peanut, corn, sunflower and poppy seed.</div></td><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Source=Constituent of the essential fatty acids (vitamin F) and of various microorganisms; oils of cottonseed, soybean, peanut, corn, sunflower and poppy seed.</div></td></tr>
<tr><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Chemical Synthesis=</div></td><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Chemical Synthesis=</div></td></tr>
<tr><td class="diff-marker" data-marker="−"></td><td style="color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #ffe49c; vertical-align: top; white-space: pre-wrap;"><div>|Metabolism=Linoleic acid (18:2n-6) is synthesized from oleic acid (18:1n-9) by desaturation of <del style="font-weight: bold; text-decoration: none;"><FONT FACE="Symbol">D</FONT>12</del>-desaturase, and <del style="font-weight: bold; text-decoration: none;"><FONT FACE="Symbol">a</FONT></del>-linolenic acid (18:3n-3) is formed from linoleic acid by desaturation reaction of <del style="font-weight: bold; text-decoration: none;"><FONT FACE="Symbol">D</FONT>15</del>-desaturase. Since both <del style="font-weight: bold; text-decoration: none;"><FONT FACE="Symbol">D</FONT>12</del>- and 15-desaturases are present in plant cells but not in animal cells, linoleic and <del style="font-weight: bold; text-decoration: none;"><FONT FACE="Symbol">a</FONT></del>-linolenic acid are not biosynthesized in animal cells in vivo. When ingested by animals, linoleic acid is desaturated, elongated to form <del style="font-weight: bold; text-decoration: none;"><FONT FACE="Symbol">g</FONT></del>-linolenic acid (18:3n-6), dihomo-<del style="font-weight: bold; text-decoration: none;"><FONT FACE="Symbol">g</FONT></del>-linolenic acid (20:3n-6), arachidonic acid (20:4n-6) and adrenic acid (22:4n-6). Docosapentaenoic acid (22:5n-6) is synthesized from adrenic acid in significant amounts only under conditions of prolonged n-3 fatty acid deficiency., No interconversion between the n-6 and n-3 series in mammals. Nutritionally, it is important to note that different foods contain different proportions of n-6/n-3 and therefore the n-6/n-3 ratio in tissue lipids change significantly depending on the choice of foods.[[Reference:Okuyama_H:Kobayashi_T:Watanabe_S:,Prog. Lipid Res.,1996,35,409|{{RelationTable/GetFirstAuthor|Reference:Okuyama_H:Kobayashi_T:Watanabe_S:,Prog. Lipid Res.,1996,35,409}}]] Although plants synthesize and store linoleic acid and <del style="font-weight: bold; text-decoration: none;"><FONT FACE="Symbol">a</FONT></del>-linolenic acid as well as saturated and monounsaturated fatty acids in grains, the proportions of these fatty acids in different vegetable oils differ greatly. Safflower and sunflower oil contain high levels of linoleate, while perilla and linseed oil are rich in <del style="font-weight: bold; text-decoration: none;"><FONT FACE="Symbol">a</FONT></del>-linolenic acid.</div></td><td class="diff-marker" data-marker="+"></td><td style="color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #a3d3ff; vertical-align: top; white-space: pre-wrap;"><div>|Metabolism=Linoleic acid (18:2n-6) is synthesized from oleic acid (18:1n-9) by desaturation of <ins style="font-weight: bold; text-decoration: none;">Delta12</ins>-desaturase, and <ins style="font-weight: bold; text-decoration: none;">alpha</ins>-linolenic acid (18:3n-3) is formed from linoleic acid by desaturation reaction of <ins style="font-weight: bold; text-decoration: none;">Delta15</ins>-desaturase. Since both <ins style="font-weight: bold; text-decoration: none;">Delta12</ins>- and 15-desaturases are present in plant cells but not in animal cells, linoleic and <ins style="font-weight: bold; text-decoration: none;">alpha</ins>-linolenic acid are not biosynthesized in animal cells in vivo. When ingested by animals, linoleic acid is desaturated, elongated to form <ins style="font-weight: bold; text-decoration: none;">gamma</ins>-linolenic acid (18:3n-6), dihomo-<ins style="font-weight: bold; text-decoration: none;">gamma</ins>-linolenic acid (20:3n-6), arachidonic acid (20:4n-6) and adrenic acid (22:4n-6). Docosapentaenoic acid (22:5n-6) is synthesized from adrenic acid in significant amounts only under conditions of prolonged n-3 fatty acid deficiency., No interconversion between the n-6 and n-3 series in mammals. Nutritionally, it is important to note that different foods contain different proportions of n-6/n-3 and therefore the n-6/n-3 ratio in tissue lipids change significantly depending on the choice of foods.[[Reference:Okuyama_H:Kobayashi_T:Watanabe_S:,Prog. Lipid Res.,1996,35,409|{{RelationTable/GetFirstAuthor|Reference:Okuyama_H:Kobayashi_T:Watanabe_S:,Prog. Lipid Res.,1996,35,409}}]] Although plants synthesize and store linoleic acid and <ins style="font-weight: bold; text-decoration: none;">alpha</ins>-linolenic acid as well as saturated and monounsaturated fatty acids in grains, the proportions of these fatty acids in different vegetable oils differ greatly. Safflower and sunflower oil contain high levels of linoleate, while perilla and linseed oil are rich in <ins style="font-weight: bold; text-decoration: none;">alpha</ins>-linolenic acid.</div></td></tr>
<tr><td class="diff-marker" data-marker="−"></td><td style="color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #ffe49c; vertical-align: top; white-space: pre-wrap;"><div>|Symbol=LA / C18:2n-6 / C18:<del style="font-weight: bold; text-decoration: none;">2<FONT FACE="Symbol">w</FONT>6</del></div></td><td class="diff-marker" data-marker="+"></td><td style="color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #a3d3ff; vertical-align: top; white-space: pre-wrap;"><div>|Symbol=LA / C18:2n-6 / C18:<ins style="font-weight: bold; text-decoration: none;">2omega6</ins></div></td></tr>
<tr><td class="diff-marker" data-marker="−"></td><td style="color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #ffe49c; vertical-align: top; white-space: pre-wrap;"><div>|Biological Activity=There are two groups of essential fatty acids for mammals, the n-6 (or <del style="font-weight: bold; text-decoration: none;"><FONT FACE="Symbol">w</FONT>6</del>) and the n-3 (or <del style="font-weight: bold; text-decoration: none;"><FONT FACE="Symbol">w</FONT>3</del>). Linoleic acid (LA) is one of the n-6 essential fatty. Animals deficient in LA show the growth retardation, skin lesions, reproductive failure, fatty liver and polydipsia <!--2009-->[[Reference:Paulsrud_JR:Pensler_L:Whitten_CF:Stewart_S:Holman:RT:,Am. J. Clin. Nutr.,1972,25,897|{{RelationTable/GetFirstAuthor|Reference:Paulsrud_JR:Pensler_L:Whitten_CF:Stewart_S:Holman:RT:,Am. J. Clin. Nutr.,1972,25,897}}]]. Dietary supplementation of either linoleate, <del style="font-weight: bold; text-decoration: none;"><FONT FACE="Symbol">g</FONT></del>-linoleate or arachidonate prevents such symptoms completely. Its physiological functions appear to be mediated mainly through the hormone-like eicosanoids (prostaglandins, leukotriens and thromboxanes et al.) derived from arachidonic acid which is biosynthesized from LA. LA is also shown to be involved in control of the water impermeability of the skin and regulation of cholesterol synthesis and transport.</div></td><td class="diff-marker" data-marker="+"></td><td style="color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #a3d3ff; vertical-align: top; white-space: pre-wrap;"><div>|Biological Activity=There are two groups of essential fatty acids for mammals, the n-6 (or <ins style="font-weight: bold; text-decoration: none;">omega6</ins>) and the n-3 (or <ins style="font-weight: bold; text-decoration: none;">omega3</ins>). Linoleic acid (LA) is one of the n-6 essential fatty. Animals deficient in LA show the growth retardation, skin lesions, reproductive failure, fatty liver and polydipsia <!--2009-->[[Reference:Paulsrud_JR:Pensler_L:Whitten_CF:Stewart_S:Holman:RT:,Am. J. Clin. Nutr.,1972,25,897|{{RelationTable/GetFirstAuthor|Reference:Paulsrud_JR:Pensler_L:Whitten_CF:Stewart_S:Holman:RT:,Am. J. Clin. Nutr.,1972,25,897}}]]. Dietary supplementation of either linoleate, <ins style="font-weight: bold; text-decoration: none;">gamma</ins>-linoleate or arachidonate prevents such symptoms completely. Its physiological functions appear to be mediated mainly through the hormone-like eicosanoids (prostaglandins, leukotriens and thromboxanes et al.) derived from arachidonic acid which is biosynthesized from LA. LA is also shown to be involved in control of the water impermeability of the skin and regulation of cholesterol synthesis and transport.</div></td></tr>
<tr><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>}}</div></td><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>}}</div></td></tr>
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<tr><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>{{Lipid/Footer}}</div></td><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>{{Lipid/Footer}}</div></td></tr>
</table>
Editor
https://lipidbank.jp/mediawiki/index.php?title=LBF18206SC05&diff=49927&oldid=prev
Editor at 16:30, 26 January 2010
2010-01-26T16:30:00Z
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<td colspan="2" style="background-color: #fff; color: #202122; text-align: center;">← Older revision</td>
<td colspan="2" style="background-color: #fff; color: #202122; text-align: center;">Revision as of 01:30, 27 January 2010</td>
</tr><tr><td colspan="2" class="diff-lineno" id="mw-diff-left-l12">Line 12:</td>
<td colspan="2" class="diff-lineno">Line 12:</td></tr>
<tr><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Density=dX<sub>4</sub><sup>20</sup> 0.9031</div></td><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Density=dX<sub>4</sub><sup>20</sup> 0.9031</div></td></tr>
<tr><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Refractive=1.4711 at 20°C</div></td><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Refractive=1.4711 at 20°C</div></td></tr>
<tr><td class="diff-marker" data-marker="−"></td><td style="color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #ffe49c; vertical-align: top; white-space: pre-wrap;"><div>|Solubility=soluble in acetone, alcohol, ether and petroleum ether.[[Reference:Matthews_NL:Brode_WR:Brown_JB:,J. Am. Chem. Soc.,1941,63,1064|{{RelationTable/GetFirstAuthor|Reference:Matthews_NL:Brode_WR:Brown_JB:,J. Am. Chem. Soc.,1941,63,1064}}]][[Reference:Nicolaides_N:Laves_F:,J. Am. Chem. Soc.,1958,80,5752|{{RelationTable/GetFirstAuthor|Reference:Nicolaides_N:Laves_F:,J. Am. Chem. Soc.,1958,80,5752}}]]</div></td><td class="diff-marker" data-marker="+"></td><td style="color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #a3d3ff; vertical-align: top; white-space: pre-wrap;"><div>|Solubility=soluble in acetone, alcohol, ether and petroleum ether.<ins style="font-weight: bold; text-decoration: none;"><!--0193--></ins>[[Reference:Matthews_NL:Brode_WR:Brown_JB:,J. Am. Chem. Soc.,1941,63,1064|{{RelationTable/GetFirstAuthor|Reference:Matthews_NL:Brode_WR:Brown_JB:,J. Am. Chem. Soc.,1941,63,1064}}]][[Reference:Nicolaides_N:Laves_F:,J. Am. Chem. Soc.,1958,80,5752|{{RelationTable/GetFirstAuthor|Reference:Nicolaides_N:Laves_F:,J. Am. Chem. Soc.,1958,80,5752}}]]<ins style="font-weight: bold; text-decoration: none;"><!--0409--><!--0410--></ins></div></td></tr>
<tr><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Chromatograms=Gas liquid chromatogram {{Image200|LBF18206SC05CH0001.gif}} (provided by Dr. Akiko Horiuchi).</div></td><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Chromatograms=Gas liquid chromatogram {{Image200|LBF18206SC05CH0001.gif}} (provided by Dr. Akiko Horiuchi).</div></td></tr>
<tr><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Source=Constituent of the essential fatty acids (vitamin F) and of various microorganisms; oils of cottonseed, soybean, peanut, corn, sunflower and poppy seed.</div></td><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Source=Constituent of the essential fatty acids (vitamin F) and of various microorganisms; oils of cottonseed, soybean, peanut, corn, sunflower and poppy seed.</div></td></tr>
<tr><td colspan="2" class="diff-lineno" id="mw-diff-left-l18">Line 18:</td>
<td colspan="2" class="diff-lineno">Line 18:</td></tr>
<tr><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Metabolism=Linoleic acid (18:2n-6) is synthesized from oleic acid (18:1n-9) by desaturation of <FONT FACE="Symbol">D</FONT>12-desaturase, and <FONT FACE="Symbol">a</FONT>-linolenic acid (18:3n-3) is formed from linoleic acid by desaturation reaction of <FONT FACE="Symbol">D</FONT>15-desaturase. Since both <FONT FACE="Symbol">D</FONT>12- and 15-desaturases are present in plant cells but not in animal cells, linoleic and <FONT FACE="Symbol">a</FONT>-linolenic acid are not biosynthesized in animal cells in vivo. When ingested by animals, linoleic acid is desaturated, elongated to form <FONT FACE="Symbol">g</FONT>-linolenic acid (18:3n-6), dihomo-<FONT FACE="Symbol">g</FONT>-linolenic acid (20:3n-6), arachidonic acid (20:4n-6) and adrenic acid (22:4n-6). Docosapentaenoic acid (22:5n-6) is synthesized from adrenic acid in significant amounts only under conditions of prolonged n-3 fatty acid deficiency., No interconversion between the n-6 and n-3 series in mammals. Nutritionally, it is important to note that different foods contain different proportions of n-6/n-3 and therefore the n-6/n-3 ratio in tissue lipids change significantly depending on the choice of foods.[[Reference:Okuyama_H:Kobayashi_T:Watanabe_S:,Prog. Lipid Res.,1996,35,409|{{RelationTable/GetFirstAuthor|Reference:Okuyama_H:Kobayashi_T:Watanabe_S:,Prog. Lipid Res.,1996,35,409}}]] Although plants synthesize and store linoleic acid and <FONT FACE="Symbol">a</FONT>-linolenic acid as well as saturated and monounsaturated fatty acids in grains, the proportions of these fatty acids in different vegetable oils differ greatly. Safflower and sunflower oil contain high levels of linoleate, while perilla and linseed oil are rich in <FONT FACE="Symbol">a</FONT>-linolenic acid.</div></td><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Metabolism=Linoleic acid (18:2n-6) is synthesized from oleic acid (18:1n-9) by desaturation of <FONT FACE="Symbol">D</FONT>12-desaturase, and <FONT FACE="Symbol">a</FONT>-linolenic acid (18:3n-3) is formed from linoleic acid by desaturation reaction of <FONT FACE="Symbol">D</FONT>15-desaturase. Since both <FONT FACE="Symbol">D</FONT>12- and 15-desaturases are present in plant cells but not in animal cells, linoleic and <FONT FACE="Symbol">a</FONT>-linolenic acid are not biosynthesized in animal cells in vivo. When ingested by animals, linoleic acid is desaturated, elongated to form <FONT FACE="Symbol">g</FONT>-linolenic acid (18:3n-6), dihomo-<FONT FACE="Symbol">g</FONT>-linolenic acid (20:3n-6), arachidonic acid (20:4n-6) and adrenic acid (22:4n-6). Docosapentaenoic acid (22:5n-6) is synthesized from adrenic acid in significant amounts only under conditions of prolonged n-3 fatty acid deficiency., No interconversion between the n-6 and n-3 series in mammals. Nutritionally, it is important to note that different foods contain different proportions of n-6/n-3 and therefore the n-6/n-3 ratio in tissue lipids change significantly depending on the choice of foods.[[Reference:Okuyama_H:Kobayashi_T:Watanabe_S:,Prog. Lipid Res.,1996,35,409|{{RelationTable/GetFirstAuthor|Reference:Okuyama_H:Kobayashi_T:Watanabe_S:,Prog. Lipid Res.,1996,35,409}}]] Although plants synthesize and store linoleic acid and <FONT FACE="Symbol">a</FONT>-linolenic acid as well as saturated and monounsaturated fatty acids in grains, the proportions of these fatty acids in different vegetable oils differ greatly. Safflower and sunflower oil contain high levels of linoleate, while perilla and linseed oil are rich in <FONT FACE="Symbol">a</FONT>-linolenic acid.</div></td></tr>
<tr><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Symbol=LA / C18:2n-6 / C18:2<FONT FACE="Symbol">w</FONT>6</div></td><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Symbol=LA / C18:2n-6 / C18:2<FONT FACE="Symbol">w</FONT>6</div></td></tr>
<tr><td class="diff-marker" data-marker="−"></td><td style="color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #ffe49c; vertical-align: top; white-space: pre-wrap;"><div>|Biological Activity=There are two groups of essential fatty acids for mammals, the n-6 (or <FONT FACE="Symbol">w</FONT>6) and the n-3 (or <FONT FACE="Symbol">w</FONT>3). Linoleic acid (LA) is one of the n-6 essential fatty. Animals deficient in LA show the growth retardation, skin lesions, reproductive failure, fatty liver and polydipsia [[Reference:Paulsrud_JR:Pensler_L:Whitten_CF:Stewart_S:Holman:RT:,Am. J. Clin. Nutr.,1972,25,897|{{RelationTable/GetFirstAuthor|Reference:Paulsrud_JR:Pensler_L:Whitten_CF:Stewart_S:Holman:RT:,Am. J. Clin. Nutr.,1972,25,897}}]]. Dietary supplementation of either linoleate, <FONT FACE="Symbol">g</FONT>-linoleate or arachidonate prevents such symptoms completely. Its physiological functions appear to be mediated mainly through the hormone-like eicosanoids (prostaglandins, leukotriens and thromboxanes et al.) derived from arachidonic acid which is biosynthesized from LA. LA is also shown to be involved in control of the water impermeability of the skin and regulation of cholesterol synthesis and transport.</div></td><td class="diff-marker" data-marker="+"></td><td style="color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #a3d3ff; vertical-align: top; white-space: pre-wrap;"><div>|Biological Activity=There are two groups of essential fatty acids for mammals, the n-6 (or <FONT FACE="Symbol">w</FONT>6) and the n-3 (or <FONT FACE="Symbol">w</FONT>3). Linoleic acid (LA) is one of the n-6 essential fatty. Animals deficient in LA show the growth retardation, skin lesions, reproductive failure, fatty liver and polydipsia <ins style="font-weight: bold; text-decoration: none;"><!--2009--></ins>[[Reference:Paulsrud_JR:Pensler_L:Whitten_CF:Stewart_S:Holman:RT:,Am. J. Clin. Nutr.,1972,25,897|{{RelationTable/GetFirstAuthor|Reference:Paulsrud_JR:Pensler_L:Whitten_CF:Stewart_S:Holman:RT:,Am. J. Clin. Nutr.,1972,25,897}}]]. Dietary supplementation of either linoleate, <FONT FACE="Symbol">g</FONT>-linoleate or arachidonate prevents such symptoms completely. Its physiological functions appear to be mediated mainly through the hormone-like eicosanoids (prostaglandins, leukotriens and thromboxanes et al.) derived from arachidonic acid which is biosynthesized from LA. LA is also shown to be involved in control of the water impermeability of the skin and regulation of cholesterol synthesis and transport.</div></td></tr>
<tr><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>}}</div></td><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>}}</div></td></tr>
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https://lipidbank.jp/mediawiki/index.php?title=LBF18206SC05&diff=49926&oldid=prev
Editor at 21:00, 6 January 2010
2010-01-06T21:00:00Z
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<td colspan="2" style="background-color: #fff; color: #202122; text-align: center;">← Older revision</td>
<td colspan="2" style="background-color: #fff; color: #202122; text-align: center;">Revision as of 06:00, 7 January 2010</td>
</tr><tr><td colspan="2" class="diff-lineno" id="mw-diff-left-l11">Line 11:</td>
<td colspan="2" class="diff-lineno">Line 11:</td></tr>
<tr><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Boiling Point=229°C to 230°C at 16mmHg</div></td><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Boiling Point=229°C to 230°C at 16mmHg</div></td></tr>
<tr><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Density=dX<sub>4</sub><sup>20</sup> 0.9031</div></td><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Density=dX<sub>4</sub><sup>20</sup> 0.9031</div></td></tr>
<tr><td class="diff-marker" data-marker="−"></td><td style="color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #ffe49c; vertical-align: top; white-space: pre-wrap;"><div>|<del style="font-weight: bold; text-decoration: none;">Optical</del>=1.4711 at 20°C</div></td><td class="diff-marker" data-marker="+"></td><td style="color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #a3d3ff; vertical-align: top; white-space: pre-wrap;"><div>|<ins style="font-weight: bold; text-decoration: none;">Refractive</ins>=1.4711 at 20°C</div></td></tr>
<tr><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Solubility=soluble in acetone, alcohol, ether and petroleum ether.[[Reference:Matthews_NL:Brode_WR:Brown_JB:,J. Am. Chem. Soc.,1941,63,1064|{{RelationTable/GetFirstAuthor|Reference:Matthews_NL:Brode_WR:Brown_JB:,J. Am. Chem. Soc.,1941,63,1064}}]][[Reference:Nicolaides_N:Laves_F:,J. Am. Chem. Soc.,1958,80,5752|{{RelationTable/GetFirstAuthor|Reference:Nicolaides_N:Laves_F:,J. Am. Chem. Soc.,1958,80,5752}}]]</div></td><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Solubility=soluble in acetone, alcohol, ether and petroleum ether.[[Reference:Matthews_NL:Brode_WR:Brown_JB:,J. Am. Chem. Soc.,1941,63,1064|{{RelationTable/GetFirstAuthor|Reference:Matthews_NL:Brode_WR:Brown_JB:,J. Am. Chem. Soc.,1941,63,1064}}]][[Reference:Nicolaides_N:Laves_F:,J. Am. Chem. Soc.,1958,80,5752|{{RelationTable/GetFirstAuthor|Reference:Nicolaides_N:Laves_F:,J. Am. Chem. Soc.,1958,80,5752}}]]</div></td></tr>
<tr><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Chromatograms=Gas liquid chromatogram {{Image200|LBF18206SC05CH0001.gif}} (provided by Dr. Akiko Horiuchi).</div></td><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Chromatograms=Gas liquid chromatogram {{Image200|LBF18206SC05CH0001.gif}} (provided by Dr. Akiko Horiuchi).</div></td></tr>
<tr><td colspan="2" class="diff-lineno" id="mw-diff-left-l17">Line 17:</td>
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<tr><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Chemical Synthesis=</div></td><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Chemical Synthesis=</div></td></tr>
<tr><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Metabolism=Linoleic acid (18:2n-6) is synthesized from oleic acid (18:1n-9) by desaturation of <FONT FACE="Symbol">D</FONT>12-desaturase, and <FONT FACE="Symbol">a</FONT>-linolenic acid (18:3n-3) is formed from linoleic acid by desaturation reaction of <FONT FACE="Symbol">D</FONT>15-desaturase. Since both <FONT FACE="Symbol">D</FONT>12- and 15-desaturases are present in plant cells but not in animal cells, linoleic and <FONT FACE="Symbol">a</FONT>-linolenic acid are not biosynthesized in animal cells in vivo. When ingested by animals, linoleic acid is desaturated, elongated to form <FONT FACE="Symbol">g</FONT>-linolenic acid (18:3n-6), dihomo-<FONT FACE="Symbol">g</FONT>-linolenic acid (20:3n-6), arachidonic acid (20:4n-6) and adrenic acid (22:4n-6). Docosapentaenoic acid (22:5n-6) is synthesized from adrenic acid in significant amounts only under conditions of prolonged n-3 fatty acid deficiency., No interconversion between the n-6 and n-3 series in mammals. Nutritionally, it is important to note that different foods contain different proportions of n-6/n-3 and therefore the n-6/n-3 ratio in tissue lipids change significantly depending on the choice of foods.[[Reference:Okuyama_H:Kobayashi_T:Watanabe_S:,Prog. Lipid Res.,1996,35,409|{{RelationTable/GetFirstAuthor|Reference:Okuyama_H:Kobayashi_T:Watanabe_S:,Prog. Lipid Res.,1996,35,409}}]] Although plants synthesize and store linoleic acid and <FONT FACE="Symbol">a</FONT>-linolenic acid as well as saturated and monounsaturated fatty acids in grains, the proportions of these fatty acids in different vegetable oils differ greatly. Safflower and sunflower oil contain high levels of linoleate, while perilla and linseed oil are rich in <FONT FACE="Symbol">a</FONT>-linolenic acid.</div></td><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Metabolism=Linoleic acid (18:2n-6) is synthesized from oleic acid (18:1n-9) by desaturation of <FONT FACE="Symbol">D</FONT>12-desaturase, and <FONT FACE="Symbol">a</FONT>-linolenic acid (18:3n-3) is formed from linoleic acid by desaturation reaction of <FONT FACE="Symbol">D</FONT>15-desaturase. Since both <FONT FACE="Symbol">D</FONT>12- and 15-desaturases are present in plant cells but not in animal cells, linoleic and <FONT FACE="Symbol">a</FONT>-linolenic acid are not biosynthesized in animal cells in vivo. When ingested by animals, linoleic acid is desaturated, elongated to form <FONT FACE="Symbol">g</FONT>-linolenic acid (18:3n-6), dihomo-<FONT FACE="Symbol">g</FONT>-linolenic acid (20:3n-6), arachidonic acid (20:4n-6) and adrenic acid (22:4n-6). Docosapentaenoic acid (22:5n-6) is synthesized from adrenic acid in significant amounts only under conditions of prolonged n-3 fatty acid deficiency., No interconversion between the n-6 and n-3 series in mammals. Nutritionally, it is important to note that different foods contain different proportions of n-6/n-3 and therefore the n-6/n-3 ratio in tissue lipids change significantly depending on the choice of foods.[[Reference:Okuyama_H:Kobayashi_T:Watanabe_S:,Prog. Lipid Res.,1996,35,409|{{RelationTable/GetFirstAuthor|Reference:Okuyama_H:Kobayashi_T:Watanabe_S:,Prog. Lipid Res.,1996,35,409}}]] Although plants synthesize and store linoleic acid and <FONT FACE="Symbol">a</FONT>-linolenic acid as well as saturated and monounsaturated fatty acids in grains, the proportions of these fatty acids in different vegetable oils differ greatly. Safflower and sunflower oil contain high levels of linoleate, while perilla and linseed oil are rich in <FONT FACE="Symbol">a</FONT>-linolenic acid.</div></td></tr>
<tr><td colspan="2" class="diff-side-deleted"></td><td class="diff-marker" data-marker="+"></td><td style="color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #a3d3ff; vertical-align: top; white-space: pre-wrap;"><div><ins style="font-weight: bold; text-decoration: none;">|Symbol=LA / C18:2n-6 / C18:2<FONT FACE="Symbol">w</FONT>6</ins></div></td></tr>
<tr><td colspan="2" class="diff-side-deleted"></td><td class="diff-marker" data-marker="+"></td><td style="color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #a3d3ff; vertical-align: top; white-space: pre-wrap;"><div><ins style="font-weight: bold; text-decoration: none;">|Biological Activity=There are two groups of essential fatty acids for mammals, the n-6 (or <FONT FACE="Symbol">w</FONT>6) and the n-3 (or <FONT FACE="Symbol">w</FONT>3). Linoleic acid (LA) is one of the n-6 essential fatty. Animals deficient in LA show the growth retardation, skin lesions, reproductive failure, fatty liver and polydipsia [[Reference:Paulsrud_JR:Pensler_L:Whitten_CF:Stewart_S:Holman:RT:,Am. J. Clin. Nutr.,1972,25,897|{{RelationTable/GetFirstAuthor|Reference:Paulsrud_JR:Pensler_L:Whitten_CF:Stewart_S:Holman:RT:,Am. J. Clin. Nutr.,1972,25,897}}]]. Dietary supplementation of either linoleate, <FONT FACE="Symbol">g</FONT>-linoleate or arachidonate prevents such symptoms completely. Its physiological functions appear to be mediated mainly through the hormone-like eicosanoids (prostaglandins, leukotriens and thromboxanes et al.) derived from arachidonic acid which is biosynthesized from LA. LA is also shown to be involved in control of the water impermeability of the skin and regulation of cholesterol synthesis and transport.</ins></div></td></tr>
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