https://lipidbank.jp/mediawiki/index.php?action=history&feed=atom&title=LBF20503HP01 2026-04-30T04:04:41Z Revision history for this page on the wiki MediaWiki 1.43.0 https://lipidbank.jp/mediawiki/index.php?title=LBF20503HP01&diff=56368&oldid=prev 2010-10-27T06:06:44Z

<p>New page: {{Lipid/Header}} {{Hierarchy|{{PAGENAME}}}} {{Metabolite |LipidBank=DFA8096 |LipidMaps=- |SysName=5-Hydroperoxy-6,8,11,14,17-eicosapentaenoic acid |Common Name=&amp;&amp;5-Hydroperoxy-6,8,11,14,...</p> <p><b>New page</b></p><div>{{Lipid/Header}}<br /> <br /> {{Hierarchy|{{PAGENAME}}}}<br /> <br /> {{Metabolite<br /> |LipidBank=DFA8096<br /> |LipidMaps=-<br /> |SysName=5-Hydroperoxy-6,8,11,14,17-eicosapentaenoic acid<br /> |Common Name=&amp;&amp;5-Hydroperoxy-6,8,11,14,17-eicosapentaenoic acid&amp;&amp;<br /> |Mass Spectra=GC-EI-MS(Me-ester; after reduction and TMS-derivatization)[[Reference:Yamauchi_R:Yamada_T:Kato_K:Ueno_Y:,Agric. Biol. Chem.,1983,47,2897|{{RelationTable/GetFirstAuthor|Reference:Yamauchi_R:Yamada_T:Kato_K:Ueno_Y:,Agric. Biol. Chem.,1983,47,2897}}]][[Reference:Ochi_K:Yoshimoto_T:Yamamoto_S:Taniguchi_K:Miyamoto_T:,J. Biol. Chem.,1983,258,5754|{{RelationTable/GetFirstAuthor|Reference:Ochi_K:Yoshimoto_T:Yamamoto_S:Taniguchi_K:Miyamoto_T:,J. Biol. Chem.,1983,258,5754}}]][[Reference:Furukawa_M:Yoshimoto_T:Ochi_K:Yamamoto_S:,Biochim. Biophys. Acta,1984,795,458|{{RelationTable/GetFirstAuthor|Reference:Furukawa_M:Yoshimoto_T:Ochi_K:Yamamoto_S:,Biochim. Biophys. Acta,1984,795,458}}]][[Reference:Hammarstrom_S:,J. Biol. Chem.,1983,258,1427|{{RelationTable/GetFirstAuthor|Reference:Hammarstrom_S:,J. Biol. Chem.,1983,258,1427}}]]: m/e=404[M]; 389[M-CH3]; 314[M-HOTMS]; 303[M-(CH2)3COOCH3]; 255[M-CH2CH=CH(CH2)3CH3]; 213[303-HOTMS]; 203[SMTO=CH(CH2)3COOCH3]<br /> |UV Spectra=UV(Me-ester)[[Reference:Yamauchi_R:Yamada_T:Kato_K:Ueno_Y:,Agric. Biol. Chem.,1983,47,2897|{{RelationTable/GetFirstAuthor|Reference:Yamauchi_R:Yamada_T:Kato_K:Ueno_Y:,Agric. Biol. Chem.,1983,47,2897}}]]: conjugated diene: lambda max=235.5nm; UV(after reduction)[[Reference:Hammarstrom_S:,J. Biol. Chem.,1983,258,1427|{{RelationTable/GetFirstAuthor|Reference:Hammarstrom_S:,J. Biol. Chem.,1983,258,1427}}]]: conjugated diene: lambda =max=235nm<br /> |IR Spectra=IR(Me-ester)[[Reference:Yamauchi_R:Yamada_T:Kato_K:Ueno_Y:,Agric. Biol. Chem.,1983,47,2897|{{RelationTable/GetFirstAuthor|Reference:Yamauchi_R:Yamada_T:Kato_K:Ueno_Y:,Agric. Biol. Chem.,1983,47,2897}}]]: OOH group: 3400cm^{-1}<br /> |NMR Spectra=^1 H-NMR[[Reference:Yamauchi_R:Yamada_T:Kato_K:Ueno_Y:,Agric. Biol. Chem.,1983,47,2897|{{RelationTable/GetFirstAuthor|Reference:Yamauchi_R:Yamada_T:Kato_K:Ueno_Y:,Agric. Biol. Chem.,1983,47,2897}}]]: OOH proton: 8.5ppm<br /> |Source=Autooxidation of icosapentaenoate[[Reference:Yamauchi_R:Yamada_T:Kato_K:Ueno_Y:,Agric. Biol. Chem.,1983,47,2897|{{RelationTable/GetFirstAuthor|Reference:Yamauchi_R:Yamada_T:Kato_K:Ueno_Y:,Agric. Biol. Chem.,1983,47,2897}}]]. Oxidation of icosapentaenoate by singlet-oxygen[[Reference:Yamauchi_R:Yamada_T:Kato_K:Ueno_Y:,Agric. Biol. Chem.,1983,47,2897|{{RelationTable/GetFirstAuthor|Reference:Yamauchi_R:Yamada_T:Kato_K:Ueno_Y:,Agric. Biol. Chem.,1983,47,2897}}]]. Oxidation of icosapentaenoate in the presence of mioglobin&lt;!--8110--&gt;. It is produced from icosapentaenoate by 5-lipoxygenate of arachidonic acid&lt;!--8111--&gt;&lt;!--8112--&gt;[[Reference:Lee_TH:Drazen_JM:Lewis_RA:Austen_KF:,Prog. Biochem. Pharmacol.,1985,20,1|{{RelationTable/GetFirstAuthor|Reference:Lee_TH:Drazen_JM:Lewis_RA:Austen_KF:,Prog. Biochem. Pharmacol.,1985,20,1}}]].<br /> |Chemical Synthesis=<br /> |Metabolism=<br /> |Biological Activity=5-Hydroperoxide derivative of icosapentaenoic acid, which is produced concomitantly with action of 15-lipoxygenase against arachidonate, is further metabolized to hydroxylate and leukotrienes, but their physiological activities remain to be clarified&lt;!--8111--&gt;&lt;!--8112--&gt;[[Reference:Lee_TH:Drazen_JM:Lewis_RA:Austen_KF:,Prog. Biochem. Pharmacol.,1985,20,1|{{RelationTable/GetFirstAuthor|Reference:Lee_TH:Drazen_JM:Lewis_RA:Austen_KF:,Prog. Biochem. Pharmacol.,1985,20,1}}]].<br /> |Note=Isomerization of hydroperoxides generated from icosapentaenoete by autooxidation: the proportion of 5-, 18-isomer (outer hydroperoxides) is higher than that of other isomer (8-,9-,11-,12-,14-,15-isomer[inner hydroperoxides])&lt;!--8110--&gt;.<br /> }}<br /> <br /> {{Lipid/Footer}}</div>

Editor