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|LipidBank=DFA8083
|LipidBank=DFA8083
|LipidMaps=-
|LipidMaps=-
|SysName=12-Hydroperoxy- (cis-5,8,trans-10,cis-14) -eicosatetraenoic acid
|SysName=12-Hydroperoxy- (cis-5,cis-8,trans-10,cis-14) -eicosatetraenoic acid
|Common Name=&&12-Hydroperoxy- (5Z,8,10E,14Z) -eicosatetraenoic acid&&12-Hydroperoxy-5,8,10,14-Eicosatetraenoic Acid&&
|Common Name=&&12-Hydroperoxy- (5Z,8,10E,14Z) -eicosatetraenoic acid&&12-Hydroperoxy-5,8,10,14-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}}]][[Reference:Koshihara_Y:Mizumura_M:Murota_S:,Biochim. Biophys. Acta,1982,712,42|{{RelationTable/GetFirstAuthor|Reference:Koshihara_Y:Mizumura_M:Murota_S:,Biochim. Biophys. Acta,1982,712,42}}]][[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}}]]:m/e= GC-EI-MS(Me-ester;after reduction 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}}]]: 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: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}}]]
|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}}]][[Reference:Koshihara_Y:Mizumura_M:Murota_S:,Biochim. Biophys. Acta,1982,712,42|{{RelationTable/GetFirstAuthor|Reference:Koshihara_Y:Mizumura_M:Murota_S:,Biochim. Biophys. Acta,1982,712,42}}]][[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}}]]:m/e= GC-EI-MS(Me-ester;after reduction 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}}]]: 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: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}}]]

Latest revision as of 06:06, 5 November 2010

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Upper classes: LB LBF



12-Hydroperoxy- (5Z,8,10E,14Z) -eicosatetraenoic acid
LBF20406HP04.png
Structural Information
12-Hydroperoxy- (cis-5,cis-8,trans-10,cis-14) -eicosatetraenoic acid
  • 12-Hydroperoxy- (5Z,8,10E,14Z) -eicosatetraenoic acid
  • 12-Hydroperoxy-5,8,10,14-Eicosatetraenoic Acid
Formula C20H32O4
Exact Mass 336.23005951199997
Average Mass 336.46567999999996
SMILES CCCCCC=CCC(OO)C=CC=CCC=CCCCC(O)=O
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(12-HPETE) Spector_AA et al..
12-HPETE generated by 12-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. KoshiharaYet al. FurukawaMet al.:m/e= GC-EI-MS(Me-ester;after reduction and TBDMS) TeraoJet al.: GC-EI-MS(Me-ester; after reduction, hydrogenation and TMS) TeraoJet al. TeraoJet al. Porter_NA et al. Porter_NA et al. RabinovitchHet al.
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=232.5nm
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
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20406HP04 See above. Furukawa_M et al. 1984
n.a. LBF20406HP04 See above. Koshihara_Y et al. 1982
n.a. LBF20406HP04 See above. Peers_KE et al. 1983
n.a. LBF20406HP04 See above. Porter_NA et al. 1981
n.a. LBF20406HP04 See above. Porter_NA et al. 1979
n.a. LBF20406HP04 See above. Porter_NA et al. 1979
n.a. LBF20406HP04 See above. Rabinovitch_H et al. 1981
n.a. LBF20406HP04 See above. Spector_AA et al. 1988
n.a. LBF20406HP04 See above. Terao_J et al. 1981
n.a. LBF20406HP04 See above. Terao_J et al. 1981
n.a. LBF20406HP04 See above. Yamagata_S et al. 1983