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|Common Name=&&12-Hydroperoxy-9,13-Octadecadienoic Acid&&12-Hydroperoxy-9,13-Octadecadienoate&&
|Common Name=&&12-Hydroperoxy-9,13-Octadecadienoic Acid&&12-Hydroperoxy-9,13-Octadecadienoate&&
|Mass Spectra=GC-EI-MS(after methanolysis, reduction and trimethylsilylation)[[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:Bessler_TR:,Lipids,1979,14,961|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:Neff_WE:Bessler_TR:,Lipids,1979,14,961}}]]: m/e= 185[SMTO=CH-CH=CH-(CH2)3CH3], GC-EI-MS (after methylation, 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}}]]: m/e= 229[CH(OH)(CH2)10COOCH3], 200[(CH2)10COOCH3+H], 197[C(OH)(CH2)10CO] GC-EI-MS(after methylation, reduction, hydrogenation and trimethylsilylation)[[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}}]]
|Mass Spectra=GC-EI-MS(after methanolysis, reduction and trimethylsilylation)[[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:Bessler_TR:,Lipids,1979,14,961|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:Neff_WE:Bessler_TR:,Lipids,1979,14,961}}]]: m/e= 185[SMTO=CH-CH=CH-(CH2)3CH3], GC-EI-MS (after methylation, 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}}]]: m/e= 229[CH(OH)(CH2)10COOCH3], 200[(CH2)10COOCH3+H], 197[C(OH)(CH2)10CO] GC-EI-MS(after methylation, reduction, hydrogenation and trimethylsilylation)[[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}}]]
|IR Spectra=After methanolyzation and reduction[[Reference:Thomas_MJ:Pryor_WA:,Lipids,1980,15,544|{{RelationTable/GetFirstAuthor|Reference:Thomas_MJ:Pryor_WA:,Lipids,1980,15,544}}]][[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}}]]: isolated double bond (3013-3010, 972-971cm^- ^1 )
|IR Spectra=After methanolyzation and reduction[[Reference:Thomas_MJ:Pryor_WA:,Lipids,1980,15,544|{{RelationTable/GetFirstAuthor|Reference:Thomas_MJ:Pryor_WA:,Lipids,1980,15,544}}]][[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}}]]: isolated double bond (3013-3010, 972-971cm^{-1})
|NMR Spectra=^1 H-NMR(after methanolyzation and reduction)[[Reference:Thomas_MJ:Pryor_WA:,Lipids,1980,15,544|{{RelationTable/GetFirstAuthor|Reference:Thomas_MJ:Pryor_WA:,Lipids,1980,15,544}}]]: olefinic protons(5.55-5.59ppm), C10 (4.08-4.11ppm)
|NMR Spectra=^1 H-NMR(after methanolyzation and reduction)[[Reference:Thomas_MJ:Pryor_WA:,Lipids,1980,15,544|{{RelationTable/GetFirstAuthor|Reference:Thomas_MJ:Pryor_WA:,Lipids,1980,15,544}}]]: olefinic protons(5.55-5.59ppm), C10 (4.08-4.11ppm)
|Source=Oxidation of methyl linoleate by singlet oxygen[[Reference:Frankel_EN:,Prog. Lipid Res.,1980,19,1|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:,Prog. Lipid Res.,1980,19,1}}]]<!--8022--><!--8023-->[[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-->[[Reference:Frankel_EN:,Chem. Phys. Lipids,1987,44,73|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:,Chem. Phys. Lipids,1987,44,73}}]]<!--8030-->.
|Source=Oxidation of methyl linoleate by singlet oxygen[[Reference:Frankel_EN:,Prog. Lipid Res.,1980,19,1|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:,Prog. Lipid Res.,1980,19,1}}]]<!--8022--><!--8023-->[[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-->[[Reference:Frankel_EN:,Chem. Phys. Lipids,1987,44,73|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:,Chem. Phys. Lipids,1987,44,73}}]]<!--8030-->.

Revision as of 10:00, 25 February 2010

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Upper classes: LB LBF



IDs and Links
LipidBank DFA8004
LipidMaps LMFA01040007
CAS
KEGG {{{KEGG}}}
KNApSAcK {{{KNApSAcK}}}
mol LBF18206HP03
12-Hydroperoxy-9,13-Octadecadienoic Acid
LBF18206HP03.png
Structural Information
12-Hydroperoxy-9,13-Octadecadienoic Acid/12-Hydroperoxy-9,13-Octadecadienoate
  • 12-Hydroperoxy-9,13-Octadecadienoic Acid
  • 12-Hydroperoxy-9,13-Octadecadienoate
Formula C18H32O4
Exact Mass 312.23005951199997
Average Mass 312.44428
SMILES CCCCC=CC(OO)CC=CCCCCCCCC(O)=O
Physicochemical Information
Oxidation of methyl linoleate by singlet oxygen Frankel_EN Frankel_EN Frankel_EN Frankel_EN .
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
Spectral Information
Mass Spectra GC-EI-MS(after methanolysis, reduction and trimethylsilylation) TeraoJet al. Frankel_EN et al.: m/e= 185[SMTO=CH-CH=CH-(CH2)3CH3], GC-EI-MS (after methylation, reduction and hydrogenation) Chan_HWS : m/e= 229[CH(OH)(CH2)10COOCH3], 200[(CH2)10COOCH3+H], 197[C(OH)(CH2)10CO] GC-EI-MS(after methylation, reduction, hydrogenation and trimethylsilylation) TeraoJet al.
UV Spectra
IR Spectra After methanolyzation and reduction Thomas_MJ et al. TeraoJet al.: isolated double bond (3013-3010, 972-971cm-1)
NMR Spectra 1H-NMR(after methanolyzation and reduction) Thomas_MJ et al.: olefinic protons(5.55-5.59ppm), C10 (4.08-4.11ppm)
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF18206HP03 See above. Chan_HWS 1977
n.a. LBF18206HP03 See above. Frankel_EN 1987
n.a. LBF18206HP03 See above. Frankel_EN 1980
n.a. LBF18206HP03 See above. Frankel_EN 1983
n.a. LBF18206HP03 See above. Frankel_EN 1984
n.a. LBF18206HP03 See above. Frankel_EN et al. 1979
n.a. LBF18206HP03 See above. Fujimoto_K 1986
n.a. LBF18206HP03 See above. Logani_MK et al. 1980
n.a. LBF18206HP03 See above. Sevanian_A et al. 1985
n.a. LBF18206HP03 See above. Terao_J et al. 1977
n.a. LBF18206HP03 See above. Thomas_MJ et al. 1980


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