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|IR Spectra=Methyl ester: [[Reference:Chan_HW:Levett_G:,Lipids,1977,12,99|{{RelationTable/GetFirstAuthor|Reference:Chan_HW:Levett_G:,Lipids,1977,12,99}}]][[Reference:Gardner_HW:Weisleder_D:,Lipids,1970,5,678|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Weisleder_D:,Lipids,1970,5,678}}]][[Reference:Cannon_JA:Zilch_KT:Burket_SC:Dutton_HJ:,J. Am. Oil Chem. Soc.,1952,29,447|{{RelationTable/GetFirstAuthor|Reference:Cannon_JA:Zilch_KT:Burket_SC:Dutton_HJ:,J. Am. Oil Chem. Soc.,1952,29,447}}]][[Reference:Privett_OS:Lundberg_WO:Khan_NA:Tolberg_WE:Wheeler_DH:,J. Am. Oil Chem. Soc.,1953,30,61|{{RelationTable/GetFirstAuthor|Reference:Privett_OS:Lundberg_WO:Khan_NA:Tolberg_WE:Wheeler_DH:,J. Am. Oil Chem. Soc.,1953,30,61}}]][[Reference:Sephton_HH:Sutton_DA:,J. Am. Oil Chem. Soc.,1956,33,263|{{RelationTable/GetFirstAuthor|Reference:Sephton_HH:Sutton_DA:,J. Am. Oil Chem. Soc.,1956,33,263}}]][[Reference:Graveland_A_:,J. Am. Oil Chem. Soc.,1970,47,352|{{RelationTable/GetFirstAuthor|Reference:Graveland_A_:,J. Am. Oil Chem. Soc.,1970,47,352}}]][[Reference:Privett_OS:Nickell_C:Lundberg_WO:Boyer_PD:,J. Am. Oil Chem. Soc.,1955,32,505|{{RelationTable/GetFirstAuthor|Reference:Privett_OS:Nickell_C:Lundberg_WO:Boyer_PD:,J. Am. Oil Chem. Soc.,1955,32,505}}]][[Reference:Gardner_HW:Weisleder_D:,Lipids,1972,7,191|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Weisleder_D:,Lipids,1972,7,191}}]]: trans, cis isomer: 986 and 949cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>, trans, trans isomer: 989cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>, OOH group: 3550cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>
|IR Spectra=Methyl ester: [[Reference:Chan_HW:Levett_G:,Lipids,1977,12,99|{{RelationTable/GetFirstAuthor|Reference:Chan_HW:Levett_G:,Lipids,1977,12,99}}]][[Reference:Gardner_HW:Weisleder_D:,Lipids,1970,5,678|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Weisleder_D:,Lipids,1970,5,678}}]][[Reference:Cannon_JA:Zilch_KT:Burket_SC:Dutton_HJ:,J. Am. Oil Chem. Soc.,1952,29,447|{{RelationTable/GetFirstAuthor|Reference:Cannon_JA:Zilch_KT:Burket_SC:Dutton_HJ:,J. Am. Oil Chem. Soc.,1952,29,447}}]][[Reference:Privett_OS:Lundberg_WO:Khan_NA:Tolberg_WE:Wheeler_DH:,J. Am. Oil Chem. Soc.,1953,30,61|{{RelationTable/GetFirstAuthor|Reference:Privett_OS:Lundberg_WO:Khan_NA:Tolberg_WE:Wheeler_DH:,J. Am. Oil Chem. Soc.,1953,30,61}}]][[Reference:Sephton_HH:Sutton_DA:,J. Am. Oil Chem. Soc.,1956,33,263|{{RelationTable/GetFirstAuthor|Reference:Sephton_HH:Sutton_DA:,J. Am. Oil Chem. Soc.,1956,33,263}}]][[Reference:Graveland_A_:,J. Am. Oil Chem. Soc.,1970,47,352|{{RelationTable/GetFirstAuthor|Reference:Graveland_A_:,J. Am. Oil Chem. Soc.,1970,47,352}}]][[Reference:Privett_OS:Nickell_C:Lundberg_WO:Boyer_PD:,J. Am. Oil Chem. Soc.,1955,32,505|{{RelationTable/GetFirstAuthor|Reference:Privett_OS:Nickell_C:Lundberg_WO:Boyer_PD:,J. Am. Oil Chem. Soc.,1955,32,505}}]][[Reference:Gardner_HW:Weisleder_D:,Lipids,1972,7,191|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Weisleder_D:,Lipids,1972,7,191}}]]: trans, cis isomer: 986 and 949cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>, trans, trans isomer: 989cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>, OOH group: 3550cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>
|NMR Spectra=<SUP><FONT SIZE=-1>1</FONT></SUP>H-NMR[[Reference:Chan_HW:Levett_G:,Lipids,1977,12,99|{{RelationTable/GetFirstAuthor|Reference:Chan_HW:Levett_G:,Lipids,1977,12,99}}]][[Reference:Frankel_EN:Neff_WE:Rohwedder_WK:Khambay_BP:Garwood_RF:Weedon_BC:,Lipids,1977,12,908|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:Neff_WE:Rohwedder_WK:Khambay_BP:Garwood_RF:Weedon_BC:,Lipids,1977,12,908}}]], <SUP><FONT SIZE=-1>1</FONT></SUP>H-NMR( after methanolyzation and reduction)[[Reference:Gardner_HW:Weisleder_D:,Lipids,1970,5,678|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Weisleder_D:,Lipids,1970,5,678}}]][[Reference:Neff_WE:Frankel_EN:Scholfield_CR:Wesleder_D:,Lipids,1978,13,415|{{RelationTable/GetFirstAuthor|Reference:Neff_WE:Frankel_EN:Scholfield_CR:Wesleder_D:,Lipids,1978,13,415}}]]: trans,cis isomer: C10-13 (5.42-6.48ppm), C14 (2.10-2.18ppm), C9(4.15ppm), J10-11= 15.4Hz(trans), J12-13= 10.8Hz (cis), trans, trans isomer: olefinic protons (5.41ppm), C14 (2.07ppm), C9 (4.20ppm)
|NMR Spectra=<SUP><FONT SIZE=-1>1</FONT></SUP>H-NMR[[Reference:Chan_HW:Levett_G:,Lipids,1977,12,99|{{RelationTable/GetFirstAuthor|Reference:Chan_HW:Levett_G:,Lipids,1977,12,99}}]][[Reference:Frankel_EN:Neff_WE:Rohwedder_WK:Khambay_BP:Garwood_RF:Weedon_BC:,Lipids,1977,12,908|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:Neff_WE:Rohwedder_WK:Khambay_BP:Garwood_RF:Weedon_BC:,Lipids,1977,12,908}}]], <SUP><FONT SIZE=-1>1</FONT></SUP>H-NMR( after methanolyzation and reduction)[[Reference:Gardner_HW:Weisleder_D:,Lipids,1970,5,678|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Weisleder_D:,Lipids,1970,5,678}}]][[Reference:Neff_WE:Frankel_EN:Scholfield_CR:Wesleder_D:,Lipids,1978,13,415|{{RelationTable/GetFirstAuthor|Reference:Neff_WE:Frankel_EN:Scholfield_CR:Wesleder_D:,Lipids,1978,13,415}}]]: trans,cis isomer: C10-13 (5.42-6.48ppm), C14 (2.10-2.18ppm), C9(4.15ppm), J10-11= 15.4Hz(trans), J12-13= 10.8Hz (cis), trans, trans isomer: olefinic protons (5.41ppm), C14 (2.07ppm), C9 (4.20ppm)
|Source=Auto oxidation of methyllinoleate[[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:Frankel_EN:,Chem. Phys. Lipids,1987,44,73|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:,Chem. Phys. Lipids,1987,44,73}}]][[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 methyl linoleate by singlet oxygen[[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:Frankel_EN:,Chem. Phys. Lipids,1987,44,73|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:,Chem. Phys. Lipids,1987,44,73}}]][[Reference:Frankel_EN:,Prog. Lipid Res.,1980,19,1|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:,Prog. Lipid Res.,1980,19,1}}]];>. Oxidation of linoleic acid by lipoxygenase[[Reference:Mathuo_M:,Fragrance J. (in Japanese),1986,76,15|{{RelationTable/GetFirstAuthor|Reference:Mathuo_M:,Fragrance J. (in Japanese),1986,76,15}}]][[Reference:Wakabayashi_T:,Chemistry and Biology (in Japanese),1980,18,558|{{RelationTable/GetFirstAuthor|Reference:Wakabayashi_T:,Chemistry and Biology (in Japanese),1980,18,558}}]];>. Production mechanism (auto oxidation): bis-allylic hydrogen at C11.
|Chemical Synthesis=
|Metabolism=
}}
}}


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Revision as of 22:00, 24 November 2009

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Upper classes: LB LBF



9-Hydroperoxy-10,12-Octadecadienoic Acid
LBF18206HP01.png
Structural Information
9-Hydroperoxy-10,12-Octadecadienoic Acid/9-Hydroperoxy-10,12-Octadecadienoate
  • 9-Hydroperoxy-10,12-Octadecadienoic Acid
  • 9-Hydroperoxy-10,12-Octadecadienoate
Formula C18H32O4
Exact Mass 312.23005951199997
Average Mass 312.44428
SMILES CCCCCC=CC=CC(OO)CCCCCCCC(O)=O
Physicochemical Information
Auto oxidation of methyllinoleate Frankel_EN Frankel_EN Frankel_EN Frankel_EN Chan_HWS et al.;>. Oxidation of methyl linoleate by singlet oxygen Frankel_EN Frankel_EN Frankel_EN Frankel_EN ;>. Oxidation of linoleic acid by lipoxygenase Mathuo_M Wakabayashi_T ;>. Production mechanism (auto oxidation): bis-allylic hydrogen at C11.
Spectral Information
Mass Spectra GC/EI-MS(after methanolysis, reduction and trimethylsilylation) Frankel_EN et al. KleimanRet al. Gardner_HW et al. Frankel_EN et al. HambergM: m/e= 382[M], 292[M-HOTMS], 311[M-(CH2)4CH3], 225[M-(CH2)7COOCH3] standard peak/ GC-EI-MS(after methylation, reduction and hydrogenation) Chan_HWS DolevAet al. Zimmerman_DC et al.: m/e= 187[CH(OH)(CH2)7COOCH3], 158[(CH2)7COOCH3+H], 155[C(OH)-(CH)7CO]
UV Spectra Trans, cis isomer: l max=236nm, e =25900, trans, trans isomer: l max=233nm, e=28600 Chan_HW et al. Bolland_JL et al. Lundberg_WO et al. Lundberg_WO et al. Gardner_HW et al. Gardner_HW et al.
IR Spectra Methyl ester: Chan_HW et al. Gardner_HW et al. Cannon_JA et al. Privett_OS et al. Sephton_HH et al. Graveland_A_ Privett_OS et al. Gardner_HW et al.: trans, cis isomer: 986 and 949cm-1, trans, trans isomer: 989cm-1, OOH group: 3550cm-1
NMR Spectra 1H-NMR Chan_HW et al. Frankel_EN et al., 1H-NMR( after methanolyzation and reduction) Gardner_HW et al. Neff_WE et al.: trans,cis isomer: C10-13 (5.42-6.48ppm), C14 (2.10-2.18ppm), C9(4.15ppm), J10-11= 15.4Hz(trans), J12-13= 10.8Hz (cis), trans, trans isomer: olefinic protons (5.41ppm), C14 (2.07ppm), C9 (4.20ppm)
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF18206HP01 See above. Bolland_JL et al. 1945
n.a. LBF18206HP01 See above. Cannon_JA et al. 1952
n.a. LBF18206HP01 See above. Chan_HW et al. 1977
n.a. LBF18206HP01 See above. Chan_HWS 1977
n.a. LBF18206HP01 See above. Chan_HWS et al. 1982
n.a. LBF18206HP01 See above. Dolev_A et al. 1967
n.a. LBF18206HP01 See above. Frankel_EN 1987
n.a. LBF18206HP01 See above. Frankel_EN 1980
n.a. LBF18206HP01 See above. Frankel_EN 1983
n.a. LBF18206HP01 See above. Frankel_EN 1984
n.a. LBF18206HP01 See above. Frankel_EN et al. 1979
n.a. LBF18206HP01 See above. Frankel_EN et al. 1977
n.a. LBF18206HP01 See above. Fujimoto_K 1986
n.a. LBF18206HP01 See above. Gardner_HW et al. 1974
n.a. LBF18206HP01 See above. Gardner_HW et al. 1970
n.a. LBF18206HP01 See above. Gardner_HW et al. 1972
n.a. LBF18206HP01 See above. Graveland_A_ 1970
n.a. LBF18206HP01 See above. Hamberg_M 1975
n.a. LBF18206HP01 See above. Kleiman_R et al. 1973
n.a. LBF18206HP01 See above. Logani_MK et al. 1980
n.a. LBF18206HP01 See above. Lundberg_WO et al. 1947
n.a. LBF18206HP01 See above. Lundberg_WO et al. 1949
n.a. LBF18206HP01 See above. Mathuo_M 1986
n.a. LBF18206HP01 See above. Neff_WE et al. 1978
n.a. LBF18206HP01 See above. Privett_OS et al. 1953
n.a. LBF18206HP01 See above. Privett_OS et al. 1955
n.a. LBF18206HP01 See above. Sephton_HH et al. 1956
n.a. LBF18206HP01 See above. Sevanian_A et al. 1985
n.a. LBF18206HP01 See above. Wakabayashi_T 1980
n.a. LBF18206HP01 See above. Zimmerman_DC et al. 1970