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|LipidBank=DFA8082
|LipidBank=DFA8082
|LipidMaps=LMFA03060041
|LipidMaps=LMFA03060041
|SysName=11-Hydroperoxy- (5,8,12,14) -eicosatetraenoic acid
|SysName=11-Hydroperoxy- 5,8,12,14 -eicosatetraenoic acid
|Common Name=&&11-Hydroperoxy- (5,8,12,14) -eicosatetraenoic acid&&
|Common Name=&&11-Hydroperoxy- 5,8,12,14 -eicosatetraenoic acid&&
|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}}]], GC-EI-MS(Me-ester; after reduction and TBDMS)(114), GC-EI-MS(Me-ester; after reduction, hydrogenation 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: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}}]][[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}}]][[Reference:Mayer_B:Moser_R:Gleispach_H:Kukovetz_WR:,Biochim. Biophys. Acta,1986,875,641|{{RelationTable/GetFirstAuthor|Reference:Mayer_B:Moser_R:Gleispach_H:Kukovetz_WR:,Biochim. Biophys. Acta,1986,875,641}}]], GC-EI-MS(Me-ester; after reduction, hydrogenation and TBDMS)
|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}}]], GC-EI-MS(Me-ester; after reduction and TBDMS)(114), GC-EI-MS(Me-ester; after reduction, hydrogenation 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: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}}]][[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}}]][[Reference:Mayer_B:Moser_R:Gleispach_H:Kukovetz_WR:,Biochim. Biophys. Acta,1986,875,641|{{RelationTable/GetFirstAuthor|Reference:Mayer_B:Moser_R:Gleispach_H:Kukovetz_WR:,Biochim. Biophys. Acta,1986,875,641}}]], GC-EI-MS(Me-ester; after reduction, hydrogenation and TBDMS)
|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 trans, cis diene: lambda max=236nm, conjugated trans, trans diene:  lambda max=232.5
|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 trans, cis diene: lambda max=236nm, conjugated trans, trans diene:  lambda max=232.5

Revision as of 05:52, 4 November 2010

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Upper classes: LB LBF



11-Hydroperoxy- 5,8,12,14 -eicosatetraenoic acid
LBF20406HP10.png
Structural Information
11-Hydroperoxy- 5,8,12,14 -eicosatetraenoic acid
  • 11-Hydroperoxy- 5,8,12,14 -eicosatetraenoic acid
Formula C20H32O4
Exact Mass 336.23005951199997
Average Mass 336.46567999999996
SMILES C(CC=CC=CC(OO)CC=CCC=CCCCC(O)=O)CCC
Physicochemical Information
Autooxidation of arachidonic acid Terao_J et al. Yamagata_S 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(11-HPETE).
11-HPETE generated by 11-lipoxygenase is enzymatically converted to bioactive compounds such as leukotriene and HETE Spector_AA et al..
Isomerization of hydroperoxides : Both 5- and 15-hydroperoxide were generated predominantly by autooxidation or singlet-oxygen mediated oxidation Terao_J et al. Yamagata_S 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., GC-EI-MS(Me-ester; after reduction and TBDMS)(114), GC-EI-MS(Me-ester; after reduction, hydrogenation and TMS) TeraoJet al. TeraoJet al. Porter_NA et al. Porter_NA et al. MayerBet al., GC-EI-MS(Me-ester; after reduction, hydrogenation and TBDMS)
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 trans, cis diene: λ max=236nm, conjugated trans, trans diene: λ max=232.5
IR Spectra IR Porter_NA et al.: conjugated trans, cis diene: 985, 950cm-1, OOH group: 3400cm-1, IR(Me-ester; after reduction) Porter_NA et al.conjugated trans, cis diene: 985, 950cm-1, conjugated trans, trans diene: 989cm-1
NMR Spectra
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20406HP10 See above. Mayer_B et al. 1986
n.a. LBF20406HP10 See above. Peers_KE et al. 1983
n.a. LBF20406HP10 See above. Porter_NA et al. 1981
n.a. LBF20406HP10 See above. Porter_NA et al. 1979
n.a. LBF20406HP10 See above. Porter_NA et al. 1979
n.a. LBF20406HP10 See above. Rabinovitch_H et al. 1981
n.a. LBF20406HP10 See above. Spector_AA et al. 1988
n.a. LBF20406HP10 See above. Terao_J et al. 1981
n.a. LBF20406HP10 See above. Terao_J et al. 1981
n.a. LBF20406HP10 See above. Yamagata_S et al. 1983