LBF18207HP01: Difference between revisions
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|Mass Spectra=GC-EI-MS(after methanolysis, reduction and trimethylsilylation) [[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}}]][[Reference:Kleiman_R:Spencer_GF:,J. Am. Oil Chem. Soc.,1973,50,31|{{RelationTable/GetFirstAuthor|Reference:Kleiman_R:Spencer_GF:,J. Am. Oil Chem. Soc.,1973,50,31}}]][[Reference:Frankel_EN:Neff_WE:Bessler_TR:,Lipids,1979,14,961|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:Neff_WE:Bessler_TR:,Lipids,1979,14,961}}]][[Reference:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1974,9,696|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1974,9,696}}]][[Reference:Hamberg_M:,Lipids,1975,10,87|{{RelationTable/GetFirstAuthor|Reference:Hamberg_M:,Lipids,1975,10,87}}]]: m/e= 382[M], 292[M-HOTMS], 311[M-(CH2)4CH3] standard peak,225[M-(CH2)7COOCH3] / 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}}]][[Reference:Dolev_A:Rohwedder_WK:Dutton_HJ:,Lipids,1967,2,28|{{RelationTable/GetFirstAuthor|Reference:Dolev_A:Rohwedder_WK:Dutton_HJ:,Lipids,1967,2,28}}]][[Reference:Zimmerman_DC:Vick_BA:,Lipids,1970,5,392|{{RelationTable/GetFirstAuthor|Reference:Zimmerman_DC:Vick_BA:,Lipids,1970,5,392}}]]: m/e= 243[CH(OH)(CH2)11COOCH3], 214[(CH2)11COOCH3+H], 211[C(OH(CH2)11CO] | |Mass Spectra=GC-EI-MS(after methanolysis, reduction and trimethylsilylation) [[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}}]][[Reference:Kleiman_R:Spencer_GF:,J. Am. Oil Chem. Soc.,1973,50,31|{{RelationTable/GetFirstAuthor|Reference:Kleiman_R:Spencer_GF:,J. Am. Oil Chem. Soc.,1973,50,31}}]][[Reference:Frankel_EN:Neff_WE:Bessler_TR:,Lipids,1979,14,961|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:Neff_WE:Bessler_TR:,Lipids,1979,14,961}}]][[Reference:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1974,9,696|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1974,9,696}}]][[Reference:Hamberg_M:,Lipids,1975,10,87|{{RelationTable/GetFirstAuthor|Reference:Hamberg_M:,Lipids,1975,10,87}}]]: m/e= 382[M], 292[M-HOTMS], 311[M-(CH2)4CH3] standard peak,225[M-(CH2)7COOCH3] / 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}}]][[Reference:Dolev_A:Rohwedder_WK:Dutton_HJ:,Lipids,1967,2,28|{{RelationTable/GetFirstAuthor|Reference:Dolev_A:Rohwedder_WK:Dutton_HJ:,Lipids,1967,2,28}}]][[Reference:Zimmerman_DC:Vick_BA:,Lipids,1970,5,392|{{RelationTable/GetFirstAuthor|Reference:Zimmerman_DC:Vick_BA:,Lipids,1970,5,392}}]]: m/e= 243[CH(OH)(CH2)11COOCH3], 214[(CH2)11COOCH3+H], 211[C(OH(CH2)11CO] | ||
|UV Spectra=Trans, cis isomer: lambda max= 236nm, epsilon = 26000, trans, trans isomer: lambda max= 233nm, epsilon =28600 (025/027/028/029/036) | |UV Spectra=Trans, cis isomer: lambda max= 236nm, epsilon = 26000, trans, trans isomer: lambda max= 233nm, epsilon =28600 (025/027/028/029/036) | ||
|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: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}}]]: cis, trans isomer: 986 and 949cm^- | |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: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}}]]: cis, trans isomer: 986 and 949cm^{-1}, trans, trans isomer: 989cm^{-1}, OOH group: 3550cm^{-1} | ||
|NMR Spectra=^1 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}}]]: C9-13 (5.45-6.53ppm), C13 (4.37ppm), J9-10= 11Hz (cis),J11-12=15Hz (trans) /^1 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}}]]: cis, trans isomer : olefinic protons(5.91ppm), C8 (2.10ppm), C13(4.15ppm), trans, trans isomer: olefinic protons (5.41ppm), C8 (2.07ppm) | |NMR Spectra=^1 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}}]]: C9-13 (5.45-6.53ppm), C13 (4.37ppm), J9-10= 11Hz (cis),J11-12=15Hz (trans) /^1 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}}]]: cis, trans isomer : olefinic protons(5.91ppm), C8 (2.10ppm), C13(4.15ppm), trans, trans isomer: olefinic protons (5.41ppm), C8 (2.07ppm) | ||
|Source=Auto oxidation of methyl linoleate<!--8029--><!--8021--><!--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}}]][[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}}]]<!--8030-->. Oxidation of methyl linoleate by singlet oxygen<!--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--><!--8030-->[[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<!--8023--><!--8031--><!--8032--><!--8033-->[[Reference:Mathuo_M:,Fragrance J. (in Japanese),1986,76,15|{{RelationTable/GetFirstAuthor|Reference:Mathuo_M:,Fragrance J. (in Japanese),1986,76,15}}]]<!--8035--><!--8037--><!--8038-->[[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. | |Source=Auto oxidation of methyl linoleate<!--8029--><!--8021--><!--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}}]][[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}}]]<!--8030-->. Oxidation of methyl linoleate by singlet oxygen<!--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--><!--8030-->[[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<!--8023--><!--8031--><!--8032--><!--8033-->[[Reference:Mathuo_M:,Fragrance J. (in Japanese),1986,76,15|{{RelationTable/GetFirstAuthor|Reference:Mathuo_M:,Fragrance J. (in Japanese),1986,76,15}}]]<!--8035--><!--8037--><!--8038-->[[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. |
Revision as of 10:00, 25 February 2010
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 | DFA8002 |
LipidMaps | LMFA01040001 |
CAS | |
KEGG | {{{KEGG}}} |
KNApSAcK | {{{KNApSAcK}}} |
mol | LBF18207HP01 |
13- Hydroperoxy-9,11-Octadecadienoic Acid | |
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Structural Information | |
13- Hydroperoxy-9,11-Octadecadienoic Acid/13- Hydroperoxy-9,11-Octadecadienoate | |
| |
Formula | C18H32O4 |
Exact Mass | 312.23005951199997 |
Average Mass | 312.44428 |
SMILES | CCCCCC(OO)C=CC=CCCCCCCCC(O)=O |
Physicochemical Information | |
Auto oxidation of methyl linoleate 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 . Oxidation of linoleic acid by lipoxygenase Mathuo_M Wakabayashi_T . Production mechanism (auto oxidation): bis-allylic hydrogen at C11. | |
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) Frankel_EN et al. KleimanRet al. Frankel_EN et al. Gardner_HW et al. HambergM: m/e= 382[M], 292[M-HOTMS], 311[M-(CH2)4CH3] standard peak,225[M-(CH2)7COOCH3] / GC-EI-MS(after methylation, reduction and hydrogenation) Chan_HWS DolevAet al. Zimmerman_DC et al.: m/e= 243[CH(OH)(CH2)11COOCH3], 214[(CH2)11COOCH3+H], 211[C(OH(CH2)11CO] |
UV Spectra | Trans, cis isomer: λ max= 236nm, ε = 26000, trans, trans isomer: λ max= 233nm, ε =28600 (025/027/028/029/036) |
IR Spectra | Methyl ester Chan_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.: cis, trans 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.: C9-13 (5.45-6.53ppm), C13 (4.37ppm), J9-10= 11Hz (cis),J11-12=15Hz (trans) /1H-NMR (after methanolyzation and reduction ) Gardner_HW et al. Neff_WE et al.: cis, trans isomer : olefinic protons(5.91ppm), C8 (2.10ppm), C13(4.15ppm), trans, trans isomer: olefinic protons (5.41ppm), C8 (2.07ppm) |
Other Spectra | |
Chromatograms |