LBF18207HP01: Difference between revisions

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{{Lipid/Header}}
{{Hierarchy|{{PAGENAME}}}}
{{Hierarchy|{{PAGENAME}}}}


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|LipidBank=DFA8002
|LipidBank=DFA8002
|LipidMaps=LMFA01040001
|LipidMaps=LMFA01040001
|SysName=13- Hydroperoxy-9,11-Octadecadienoic Acid/13- Hydroperoxy-9,11-Octadecadienoate
|SysName=13-Hydroperoxy-9,11-octadecadienoic acid
|Common Name=&&13- Hydroperoxy-9,11-Octadecadienoic Acid&&13- Hydroperoxy-9,11-Octadecadienoate&&
|Common Name=&&13-HPODE&&
|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: <FONT FACE="Symbol">l</FONT> max= 236nm, <FONT FACE="Symbol">e</FONT>= 26000, trans, trans isomer: <FONT FACE="Symbol">l</FONT> max= 233nm, <FONT FACE="Symbol">e</FONT>=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<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: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=<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}}]]: C9-13 (5.45-6.53ppm), C13 (4.37ppm), J9-10= 11Hz (cis),J11-12=15Hz (trans) /<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}}]]: 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.
|Chemical Synthesis=
|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-->
}}
 
{{MassbankSpectra|
UT000064
UT000065
UT000066
UT000067
UT000068
UT000069
UT000070
UT000071
UT000072
}}
}}
{{Lipid/Footer}}

Latest revision as of 00:00, 17 January 2014

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Upper classes: LB LBF



13-HPODE
LBF18207HP01.png
Structural Information
13-Hydroperoxy-9,11-octadecadienoic acid
  • 13-HPODE
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
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF18207HP01 See above. Cannon_JA et al. 1952
n.a. LBF18207HP01 See above. Chan_HW et al. 1977
n.a. LBF18207HP01 See above. Chan_HWS 1977
n.a. LBF18207HP01 See above. Chan_HWS et al. 1982
n.a. LBF18207HP01 See above. Dolev_A et al. 1967
n.a. LBF18207HP01 See above. Frankel_EN 1987
n.a. LBF18207HP01 See above. Frankel_EN 1980
n.a. LBF18207HP01 See above. Frankel_EN 1983
n.a. LBF18207HP01 See above. Frankel_EN 1984
n.a. LBF18207HP01 See above. Frankel_EN et al. 1979
n.a. LBF18207HP01 See above. Frankel_EN et al. 1977
n.a. LBF18207HP01 See above. Fujimoto_K 1986
n.a. LBF18207HP01 See above. Gardner_HW et al. 1974
n.a. LBF18207HP01 See above. Gardner_HW et al. 1970
n.a. LBF18207HP01 See above. Graveland_A_ 1970
n.a. LBF18207HP01 See above. Hamberg_M 1975
n.a. LBF18207HP01 See above. Kleiman_R et al. 1973
n.a. LBF18207HP01 See above. Logani_MK et al. 1980
n.a. LBF18207HP01 See above. Mathuo_M 1986
n.a. LBF18207HP01 See above. Neff_WE et al. 1978
n.a. LBF18207HP01 See above. Privett_OS et al. 1953
n.a. LBF18207HP01 See above. Privett_OS et al. 1955
n.a. LBF18207HP01 See above. Sephton_HH et al. 1956
n.a. LBF18207HP01 See above. Sevanian_A et al. 1985
n.a. LBF18207HP01 See above. Wakabayashi_T 1980
n.a. LBF18207HP01 See above. Zimmerman_DC et al. 1970