LBF20406HP03: Difference between revisions

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{{Lipid/Header}}
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|LipidBank=DFA8081
|LipidBank=DFA8081
|LipidMaps=-
|LipidMaps=-
|SysName=9-Hydroperoxy-5,7,11,14-Eicosatetraenoic Acid/9-Hydroperoxy-5,7,11,14-Eicosatetraenoate
|SysName=9-Hydroperoxy- 5,7,11,14 -eicosatetraenoic acid
|Mass Spectra=GC-EI-MS(Me-ester; after reduction and TMS)<<8080/8098/8116>>: m/e=406[M]; 316[M-HOTMS]; 255[SMTO=CHCH=CHCH=CH(CH2)3COOCH3]; GC-EI-MS(Me-ester; after reduction and TBDMS)(114): m/e=448[M], 391[M-(CH3)3C]; GC-EI-MS(Me-ester; after reduction hydrogenation and TMS)
|Common Name=&&9-Hydroperoxy- 5,7,11,14 -eicosatetraenoic acid&&
|UV Spectra=UV<<8099>> conjugated diene: <FONT FACE="Symbol">l</FONT>max=235nm, UV(Me-ester)<<8098>> conjugated diene: <FONT FACE="Symbol">l</FONT>max=232.5nm, UV(Me-ester; after reduction)<<8105>> conjugated cis, trans diene: <FONT FACE="Symbol">l</FONT>max=236nm, conjugated trans, trans diene: <FONT FACE="Symbol">l</FONT>max=232.
|Mass Spectra=GC-EI-MS(Me-ester; after reduction and TMS)[[Reference:Terao_J:Matsushita_S:,Agric. Biol. Chem.,1981,45,595|{{RelationTable/GetFirstAuthor|Reference:Terao_J:Matsushita_S:,Agric. Biol. Chem.,1981,45,595}}]][[Reference:Terao_J:Matsushita_S:,Agric. Biol. Chem.,1981,45,587|{{RelationTable/GetFirstAuthor|Reference:Terao_J:Matsushita_S:,Agric. Biol. Chem.,1981,45,587}}]][[Reference:Rabinovitch_H:Durand_J:Rigaud_M:Mendy_F:Breton_JC:,Lipids,1981,16,518|{{RelationTable/GetFirstAuthor|Reference:Rabinovitch_H:Durand_J:Rigaud_M:Mendy_F:Breton_JC:,Lipids,1981,16,518}}]]: m/e=406[M]; 316[M-HOTMS]; 255[SMTO=CHCH=CHCH=CH(CH2)3COOCH3]; GC-EI-MS(Me-ester; after reduction and TBDMS)(114): m/e=448[M], 391[M-(CH3)3C]; GC-EI-MS(Me-ester; after reduction hydrogenation and TMS)
|IR Spectra=IR(me-ester; after reduction)<<8105>> conjugated cis, trans diene: 985, 950cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>, conjugated trans, trans diene: 989cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>
|UV Spectra=UV[[Reference:Porter_NA:Logan_J:Kontoyiannidou_V:,J. Org. Chem.,1979,44,3177|{{RelationTable/GetFirstAuthor|Reference:Porter_NA:Logan_J:Kontoyiannidou_V:,J. Org. Chem.,1979,44,3177}}]] conjugated diene: lambda max=235nm, UV(Me-ester)[[Reference:Terao_J:Matsushita_S:,Agric. Biol. Chem.,1981,45,587|{{RelationTable/GetFirstAuthor|Reference:Terao_J:Matsushita_S:,Agric. Biol. Chem.,1981,45,587}}]] conjugated diene: lambda max=232.5nm, UV(Me-ester; after reduction)[[Reference:Porter_NA:Wolf_RA:Yarbro_EM:Weenen_H:,Biochem. Biophys. Res. Commun.,1979,89,1058|{{RelationTable/GetFirstAuthor|Reference:Porter_NA:Wolf_RA:Yarbro_EM:Weenen_H:,Biochem. Biophys. Res. Commun.,1979,89,1058}}]] conjugated cis, trans diene: lambda max=236nm, conjugated trans, trans diene: lambda max=232nm.
|NOTE Spectra=Rogenation and TBDMS)<<8098>>
|IR Spectra=IR(me-ester; after reduction)[[Reference:Porter_NA:Wolf_RA:Yarbro_EM:Weenen_H:,Biochem. Biophys. Res. Commun.,1979,89,1058|{{RelationTable/GetFirstAuthor|Reference:Porter_NA:Wolf_RA:Yarbro_EM:Weenen_H:,Biochem. Biophys. Res. Commun.,1979,89,1058}}]] conjugated cis, trans diene: 985, 950cm^{-1}, conjugated trans, trans diene: 989cm^{-1}
|Other Spectra= Hydrogenation and TBDMS[[Reference:Terao_J:Matsushita_S:,Agric. Biol. Chem.,1981,45,587|{{RelationTable/GetFirstAuthor|Reference:Terao_J:Matsushita_S:,Agric. Biol. Chem.,1981,45,587}}]]
|Source=Autooxidation of arachidonic acid[[Reference:Terao_J:Matsushita_S:,Agric. Biol. Chem.,1981,45,595|{{RelationTable/GetFirstAuthor|Reference:Terao_J:Matsushita_S:,Agric. Biol. Chem.,1981,45,595}}]][[Reference:Porter_NA:Wolf_RA:Yarbro_EM:Weenen_H:,Biochem. Biophys. Res. Commun.,1979,89,1058|{{RelationTable/GetFirstAuthor|Reference:Porter_NA:Wolf_RA:Yarbro_EM:Weenen_H:,Biochem. Biophys. Res. Commun.,1979,89,1058}}]]. Oxidation of arachidonic acid by singlet-oxygen[[Reference:Terao_J:Matsushita_S:,Agric. Biol. Chem.,1981,45,587|{{RelationTable/GetFirstAuthor|Reference:Terao_J:Matsushita_S:,Agric. Biol. Chem.,1981,45,587}}]][[Reference:Porter_NA:Logan_J:Kontoyiannidou_V:,J. Org. Chem.,1979,44,3177|{{RelationTable/GetFirstAuthor|Reference:Porter_NA:Logan_J:Kontoyiannidou_V:,J. Org. Chem.,1979,44,3177}}]]. Reaction products between arachidonic acid and lipoxygenase from living cells(9-HPETE)<!--8100--><!--8102-->.
|Chemical Synthesis=
|Metabolism=
|Biological Activity=9-HPETE generated by 9-lipoxygenase is enzymatically converted to bioactive compounds such as leukotriene and HETE<!--8100-->.
|Note=Isomerization of hydroperoxides : Both 5- and 15-hydroperoxide were generated predominantly by autooxidation or singlet-oxygen mediated oxidation[[Reference:Terao_J:Matsushita_S:,Agric. Biol. Chem.,1981,45,595|{{RelationTable/GetFirstAuthor|Reference:Terao_J:Matsushita_S:,Agric. Biol. Chem.,1981,45,595}}]]<!--[[Reference:Yamagata_S:Murakami_H:Terao_J:Matsushita_S:,Agric. Biol. Chem.,1983,47,2791|{{RelationTable/GetFirstAuthor|Reference:Yamagata_S:Murakami_H:Terao_J:Matsushita_S:,Agric. Biol. Chem.,1983,47,2791}}]]-->[[Reference:Peers_KE:Coxon_DT:,Chem. Phys. Lipids,1983,32,49|{{RelationTable/GetFirstAuthor|Reference:Peers_KE:Coxon_DT:,Chem. Phys. Lipids,1983,32,49}}]]. However, the proportion of each isomer generated become almost equal by supplementation of hydrogen donor such as tocopherol[[Reference:Porter_NA:Lehman_IS:Weber_BA:Smith_KJ:,J. Am. Chem. Soc.,1981,103,6447|{{RelationTable/GetFirstAuthor|Reference:Porter_NA:Lehman_IS:Weber_BA:Smith_KJ:,J. Am. Chem. Soc.,1981,103,6447}}]][[Reference:Terao_J:Matsushita_S:,Agric. Biol. Chem.,1981,45,595|{{RelationTable/GetFirstAuthor|Reference:Terao_J:Matsushita_S:,Agric. Biol. Chem.,1981,45,595}}]][[Reference:Peers_KE:Coxon_DT:,Chem. Phys. Lipids,1983,32,49|{{RelationTable/GetFirstAuthor|Reference:Peers_KE:Coxon_DT:,Chem. Phys. Lipids,1983,32,49}}]].
}}
}}
{{Lipid/Footer}}

Latest revision as of 01:32, 12 November 2010

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Upper classes: LB LBF



IDs and Links
LipidBank DFA8081
LipidMaps -
CAS
KEGG {{{KEGG}}}
KNApSAcK {{{KNApSAcK}}}
mol LBF20406HP03
9-Hydroperoxy- 5,7,11,14 -eicosatetraenoic acid
LBF20406HP03.png
Structural Information
9-Hydroperoxy- 5,7,11,14 -eicosatetraenoic acid
  • 9-Hydroperoxy- 5,7,11,14 -eicosatetraenoic acid
Formula C20H32O4
Exact Mass 336.23005951199997
Average Mass 336.46567999999996
SMILES C(CC=CCC=CCC(OO)C=CC=CCCCC(O)=O)CCC
Physicochemical Information
Autooxidation of arachidonic acid Terao_J et al. Porter_NA et al.. Oxidation of arachidonic acid by singlet-oxygen Terao_J et al. Porter_NA et al.. Reaction products between arachidonic acid and lipoxygenase from living cells(9-HPETE).
9-HPETE generated by 9-lipoxygenase is enzymatically converted to bioactive compounds such as leukotriene and HETE.
Isomerization of hydroperoxides : Both 5- and 15-hydroperoxide were generated predominantly by autooxidation or singlet-oxygen mediated oxidation Terao_J et al. Peers_KE et al.. However, the proportion of each isomer generated become almost equal by supplementation of hydrogen donor such as tocopherol Porter_NA et al. Terao_J et al. Peers_KE et al..
Spectral Information
Mass Spectra GC-EI-MS(Me-ester; after reduction and TMS) TeraoJet al. TeraoJet al. RabinovitchHet al.: m/e=406[M]; 316[M-HOTMS]; 255[SMTO=CHCH=CHCH=CH(CH2)3COOCH3]; GC-EI-MS(Me-ester; after reduction and TBDMS)(114): m/e=448[M], 391[M-(CH3)3C]; GC-EI-MS(Me-ester; after reduction hydrogenation and TMS)
UV Spectra UV Porter_NA et al. conjugated diene: λ max=235nm, UV(Me-ester) TeraoJet al. conjugated diene: λ max=232.5nm, UV(Me-ester; after reduction) Porter_NA et al. conjugated cis, trans diene: λ max=236nm, conjugated trans, trans diene: λ max=232nm.
IR Spectra IR(me-ester; after reduction) Porter_NA et al. conjugated cis, trans diene: 985, 950cm-1, conjugated trans, trans diene: 989cm-1
NMR Spectra
Other Spectra Hydrogenation and TBDMS TeraoJet al.
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20406HP03 See above. Peers_KE et al. 1983
n.a. LBF20406HP03 See above. Porter_NA et al. 1981
n.a. LBF20406HP03 See above. Porter_NA et al. 1979
n.a. LBF20406HP03 See above. Porter_NA et al. 1979
n.a. LBF20406HP03 See above. Rabinovitch_H et al. 1981
n.a. LBF20406HP03 See above. Terao_J et al. 1981
n.a. LBF20406HP03 See above. Terao_J et al. 1981
n.a. LBF20406HP03 See above. Yamagata_S et al. 1983


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