LBF18303HP01: Difference between revisions
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|LipidBank=DFA8050 | |LipidBank=DFA8050 | ||
|LipidMaps=LMFA01040013 | |LipidMaps=LMFA01040013 | ||
|SysName=9-Hydroperoxy-10,12,15- | |SysName=9-Hydroperoxy-10,12,15-octadecatrienoic acid | ||
|Common Name=&&9- | |Common Name=&&9-HpOTrE&& | ||
|Mass Spectra=EI-MS(Me-ester; after reduction and hydrogenation)[[Reference:Chan_HWS:,J. Am. Oil Chem. Soc.,1977,54,100|{{RelationTable/GetFirstAuthor|Reference:Chan_HWS:,J. Am. Oil Chem. Soc.,1977,54,100}}]][[Reference:Chan_HWS:Levett_G:,Lipids,1977,12,837|{{RelationTable/GetFirstAuthor|Reference:Chan_HWS:Levett_G:,Lipids,1977,12,837}}]]: m/e=187[O=CH(CH2)7C(=OH)OCH3]; 158[CH2(CH2)6C(=OH)OCH3]; 155[O=CH(CH2)7C=O], GC-EI-MS(Me-ester; after reduction and TMS)[[Reference:Terao_J:Matsushita_S:,J. Am. Oil Chem. Soc.,1977,54,234|{{RelationTable/GetFirstAuthor|Reference:Terao_J:Matsushita_S:,J. Am. Oil Chem. Soc.,1977,54,234}}]][[Reference:Frankel_EN:Neff_WE:Rohwedder_WK:Khambay_BPS:Garwood_RF:Weedon_BCL:,Lipids,1977,12,1055|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:Neff_WE:Rohwedder_WK:Khambay_BPS:Garwood_RF:Weedon_BCL:,Lipids,1977,12,1055}}]]: m/e=380[M]; 365[M-CH3]; 223[SMTO=CH-CH=CH-CH=CH-CH2-CH=CH-CH2CH3] | |Mass Spectra=EI-MS(Me-ester; after reduction and hydrogenation)[[Reference:Chan_HWS:,J. Am. Oil Chem. Soc.,1977,54,100|{{RelationTable/GetFirstAuthor|Reference:Chan_HWS:,J. Am. Oil Chem. Soc.,1977,54,100}}]][[Reference:Chan_HWS:Levett_G:,Lipids,1977,12,837|{{RelationTable/GetFirstAuthor|Reference:Chan_HWS:Levett_G:,Lipids,1977,12,837}}]]: m/e=187[O=CH(CH2)7C(=OH)OCH3]; 158[CH2(CH2)6C(=OH)OCH3]; 155[O=CH(CH2)7C=O], GC-EI-MS(Me-ester; after reduction and TMS)[[Reference:Terao_J:Matsushita_S:,J. Am. Oil Chem. Soc.,1977,54,234|{{RelationTable/GetFirstAuthor|Reference:Terao_J:Matsushita_S:,J. Am. Oil Chem. Soc.,1977,54,234}}]][[Reference:Frankel_EN:Neff_WE:Rohwedder_WK:Khambay_BPS:Garwood_RF:Weedon_BCL:,Lipids,1977,12,1055|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:Neff_WE:Rohwedder_WK:Khambay_BPS:Garwood_RF:Weedon_BCL:,Lipids,1977,12,1055}}]]: m/e=380[M]; 365[M-CH3]; 223[SMTO=CH-CH=CH-CH=CH-CH2-CH=CH-CH2CH3] | ||
|UV Spectra=(Me-ester; after reduction; in | |UV Spectra=(Me-ester; after reduction; in ethanol)[[Reference:Chan_HWS:Levett_G:,Lipids,1977,12,837|{{RelationTable/GetFirstAuthor|Reference:Chan_HWS:Levett_G:,Lipids,1977,12,837}}]], trans, cis, cis isomer: lambda max=236nm trans, trans, cis isomer: lambda max=232nm | ||
|IR Spectra=(Me-ester; after reduction)[[Reference:Chan_HWS:Levett_G:,Lipids,1977,12,837|{{RelationTable/GetFirstAuthor|Reference:Chan_HWS:Levett_G:,Lipids,1977,12,837}}]][[Reference:Frankel_EN:Neff_WE:Rohwedder_WK:Khambay_BPS:Garwood_RF:Weedon_BCL:,Lipids,1977,12,1055|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:Neff_WE:Rohwedder_WK:Khambay_BPS:Garwood_RF:Weedon_BCL:,Lipids,1977,12,1055}}]], trans, cis, cis isomer:9 88-983 AND 951-945cm | |IR Spectra=(Me-ester; after reduction)[[Reference:Chan_HWS:Levett_G:,Lipids,1977,12,837|{{RelationTable/GetFirstAuthor|Reference:Chan_HWS:Levett_G:,Lipids,1977,12,837}}]][[Reference:Frankel_EN:Neff_WE:Rohwedder_WK:Khambay_BPS:Garwood_RF:Weedon_BCL:,Lipids,1977,12,1055|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:Neff_WE:Rohwedder_WK:Khambay_BPS:Garwood_RF:Weedon_BCL:,Lipids,1977,12,1055}}]], trans, cis, cis isomer:9 88-983 AND 951-945cm^{-1}; trans, trans, cis isomer: 992-983cm^{-1} (Me-ester)[[Reference:Toyoda_I:Terao_J:Matsushita_S:,Lipids,1982,17,84|{{RelationTable/GetFirstAuthor|Reference:Toyoda_I:Terao_J:Matsushita_S:,Lipids,1982,17,84}}]], OOH group: 3400cm^{-1} | ||
|Source=Auto oxidation of linoleate[[Reference:Terao_J:Matsushita_S:,J. Am. Oil Chem. Soc.,1977,54,234|{{RelationTable/GetFirstAuthor|Reference:Terao_J:Matsushita_S:,J. Am. Oil Chem. Soc.,1977,54,234}}]][[Reference:Frankel_EN:,Prog. Lipid Res.,1980,19,1|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:,Prog. Lipid Res.,1980,19,1}}]][[Reference:Frankel_EN:,Prog. Lipid Res.,1983,22,1|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:,Prog. Lipid Res.,1983,22,1}}]][[Reference:Frankel_EN:,Prog. Lipid Res.,1984,23,197|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:,Prog. Lipid Res.,1984,23,197}}]][[Reference:Chan_HWS:Coxon_DT:Peers_KE:Price_KR:,Food Chemistry,1982,9,21|{{RelationTable/GetFirstAuthor|Reference:Chan_HWS:Coxon_DT:Peers_KE:Price_KR:,Food Chemistry,1982,9,21}}]] | |Source=Auto oxidation of linoleate[[Reference:Terao_J:Matsushita_S:,J. Am. Oil Chem. Soc.,1977,54,234|{{RelationTable/GetFirstAuthor|Reference:Terao_J:Matsushita_S:,J. Am. Oil Chem. Soc.,1977,54,234}}]]<!--8022--><!--8023--><!--8021-->[[Reference:Frankel_EN:,Prog. Lipid Res.,1980,19,1|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:,Prog. Lipid Res.,1980,19,1}}]][[Reference:Frankel_EN:,Prog. Lipid Res.,1983,22,1|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:,Prog. Lipid Res.,1983,22,1}}]][[Reference:Frankel_EN:,Prog. Lipid Res.,1984,23,197|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:,Prog. Lipid Res.,1984,23,197}}]]<!--8027--><!--8030-->[[Reference:Chan_HWS:Coxon_DT:Peers_KE:Price_KR:,Food Chemistry,1982,9,21|{{RelationTable/GetFirstAuthor|Reference:Chan_HWS:Coxon_DT:Peers_KE:Price_KR:,Food Chemistry,1982,9,21}}]]. Oxidation of linoleate by singlet oxygen<!--8022--><!--8023-->[[Reference:Frankel_EN:,Prog. Lipid Res.,1980,19,1|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:,Prog. Lipid Res.,1980,19,1}}]][[Reference:Frankel_EN:,Prog. Lipid Res.,1983,22,1|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:,Prog. Lipid Res.,1983,22,1}}]][[Reference:Frankel_EN:,Prog. Lipid Res.,1984,23,197|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:,Prog. Lipid Res.,1984,23,197}}]]<!--8027--><!--8030-->. Reaction products between linoleate and linseed lipoxygenase(pH6.5, 24°C)[[Reference:Zimmerman_DC:Vick_BA:,Lipids,1970,5,392|{{RelationTable/GetFirstAuthor|Reference:Zimmerman_DC:Vick_BA:,Lipids,1970,5,392}}]]. | ||
|Chemical Synthesis= | |Chemical Synthesis= | ||
|Metabolism= | |Metabolism= | ||
|Biological Activity=Pysiological damages are induced by these hydroperoxides which are incorporated into bodies or synthesized endogenously.[[Reference:Logani_MK:Davies_RE:,Lipids,1980,15,485|{{RelationTable/GetFirstAuthor|Reference:Logani_MK:Davies_RE:,Lipids,1980,15,485}}]]<!--8044--><!--8045-->[[Reference:Sevanian_A:Hochstein_P:,Annu. Rev. Nutr.,1985,5,365|{{RelationTable/GetFirstAuthor|Reference:Sevanian_A:Hochstein_P:,Annu. Rev. Nutr.,1985,5,365}}]][[Reference:Fujimoto_K:,Fragrance J. (in Japanese),1986,76,21|{{RelationTable/GetFirstAuthor|Reference:Fujimoto_K:,Fragrance J. (in Japanese),1986,76,21}}]]<!--8048--><!--8049-->. It reacts with DNA in the presence of Fe ions and ascorbic acid[[Reference:Fujimoto_K:Neff_WE:Frankel_EN:,Biochim. Biophys. Acta,1984,795,100|{{RelationTable/GetFirstAuthor|Reference:Fujimoto_K:Neff_WE:Frankel_EN:,Biochim. Biophys. Acta,1984,795,100}}]]. | |||
}} | |||
{{MassbankSpectra| | |||
UT000262 | |||
UT000263 | |||
UT000264 | |||
UT000265 | |||
UT000266 | |||
UT000267 | |||
UT000268 | |||
UT000269 | |||
UT000270 | |||
}} | }} | ||
{{Lipid/Footer}} | {{Lipid/Footer}} |
Latest revision as of 00:00, 17 January 2014
LipidBank Top (トップ) |
Fatty acid (脂肪酸) |
Glycerolipid (グリセロ脂質) |
Sphingolipid (スフィンゴ脂質) |
Journals (雑誌一覧) |
How to edit (ページの書き方) |
IDs and Links | |
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LipidBank | DFA8050 |
LipidMaps | LMFA01040013 |
CAS | |
KEGG | {{{KEGG}}} |
KNApSAcK | {{{KNApSAcK}}} |
mol | LBF18303HP01 |
9-HpOTrE | |
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Structural Information | |
9-Hydroperoxy-10,12,15-octadecatrienoic acid | |
| |
Formula | C18H30O4 |
Exact Mass | 310.21440944799997 |
Average Mass | 310.4284 |
SMILES | CCC=CCC=CC=CC(OO)CCCCCCCC(O)=O |
Physicochemical Information | |
Auto oxidation of linoleate Terao_J et al. Frankel_EN Frankel_EN Frankel_EN Chan_HWS et al.. Oxidation of linoleate by singlet oxygen Frankel_EN Frankel_EN Frankel_EN . Reaction products between linoleate and linseed lipoxygenase(pH6.5, 24°C) Zimmerman_DC et al.. | |
Pysiological damages are induced by these hydroperoxides which are incorporated into bodies or synthesized endogenously. Logani_MK et al. Sevanian_A et al. Fujimoto_K . It reacts with DNA in the presence of Fe ions and ascorbic acid Fujimoto_K et al.. | |
Spectral Information | |
Mass Spectra | EI-MS(Me-ester; after reduction and hydrogenation) Chan_HWS Chan_HWS et al.: m/e=187[O=CH(CH2)7C(=OH)OCH3]; 158[CH2(CH2)6C(=OH)OCH3]; 155[O=CH(CH2)7C=O], GC-EI-MS(Me-ester; after reduction and TMS) TeraoJet al. Frankel_EN et al.: m/e=380[M]; 365[M-CH3]; 223[SMTO=CH-CH=CH-CH=CH-CH2-CH=CH-CH2CH3] |
UV Spectra | (Me-ester; after reduction; in ethanol) Chan_HWS et al., trans, cis, cis isomer: λ max=236nm trans, trans, cis isomer: λ max=232nm |
IR Spectra | (Me-ester; after reduction) Chan_HWS et al. Frankel_EN et al., trans, cis, cis isomer:9 88-983 AND 951-945cm-1; trans, trans, cis isomer: 992-983cm-1 (Me-ester) ToyodaIet al., OOH group: 3400cm-1 |
NMR Spectra | |
Other Spectra | |
Chromatograms |
Reported Metabolites, References | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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