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


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|LipidBank=DFA8023
|LipidBank=DFA8023
|LipidMaps=LMFA01050125
|LipidMaps=LMFA01050125
|SysName=13-Hydroxy-9,11-Octadecadienoic Acid/13-Hydroxy-9,11-Octadecadienoate
|SysName=13-Hydroxy-9,11-octadecadienoic acid
|Common Name=&&13-Hydroxy-9,11-Octadecadienoic Acid&&13-Hydroxy-9,11-Octadecadienoate&&
|Common Name=&&13-HODE&&
|Mass Spectra=GC-EI-MS(after methanolysis and trimethylsilylation)[[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:Streckert_G:Stan_HJ:,Lipids,1975,10,847|{{RelationTable/GetFirstAuthor|Reference:Streckert_G:Stan_HJ:,Lipids,1975,10,847}}]][[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: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:Lundberg_WO:Chipault_JR:Hendrickson_NJ:,J. Am. Oil Chem. Soc.,1949,26,109|{{RelationTable/GetFirstAuthor|Reference:Lundberg_WO:Chipault_JR:Hendrickson_NJ:,J. Am. Oil Chem. Soc.,1949,26,109}}]]: m/e=382[M], 367[M-CH3], 351[M-OCH3], 311[M-(CH2)4CH3], 225[M-(CH2)7COOCH3], GC-EI-MS(after methanolysis, hydrogenation and trimethylsilylation)[[Reference:Streckert_G:Stan_HJ:,Lipids,1975,10,847|{{RelationTable/GetFirstAuthor|Reference:Streckert_G:Stan_HJ:,Lipids,1975,10,847}}]][[Reference:Hamberg_M:,Lipids,1975,10,87|{{RelationTable/GetFirstAuthor|Reference:Hamberg_M:,Lipids,1975,10,87}}]], GC-EI-MS(after methanolysis and hydrogenation) [[Reference:Christophersen_BO:,Biochim. Biophys. Acta,1968,164,35|{{RelationTable/GetFirstAuthor|Reference:Christophersen_BO:,Biochim. Biophys. Acta,1968,164,35}}]]
|Mass Spectra=GC-EI-MS(after methanolysis and trimethylsilylation)[[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:Streckert_G:Stan_HJ:,Lipids,1975,10,847|{{RelationTable/GetFirstAuthor|Reference:Streckert_G:Stan_HJ:,Lipids,1975,10,847}}]][[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: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:Lundberg_WO:Chipault_JR:Hendrickson_NJ:,J. Am. Oil Chem. Soc.,1949,26,109|{{RelationTable/GetFirstAuthor|Reference:Lundberg_WO:Chipault_JR:Hendrickson_NJ:,J. Am. Oil Chem. Soc.,1949,26,109}}]]: m/e=382[M], 367[M-CH3], 351[M-OCH3], 311[M-(CH2)4CH3], 225[M-(CH2)7COOCH3], GC-EI-MS(after methanolysis, hydrogenation and trimethylsilylation)[[Reference:Streckert_G:Stan_HJ:,Lipids,1975,10,847|{{RelationTable/GetFirstAuthor|Reference:Streckert_G:Stan_HJ:,Lipids,1975,10,847}}]][[Reference:Hamberg_M:,Lipids,1975,10,87|{{RelationTable/GetFirstAuthor|Reference:Hamberg_M:,Lipids,1975,10,87}}]], GC-EI-MS(after methanolysis and hydrogenation) [[Reference:Christophersen_BO:,Biochim. Biophys. Acta,1968,164,35|{{RelationTable/GetFirstAuthor|Reference:Christophersen_BO:,Biochim. Biophys. Acta,1968,164,35}}]]
|UV Spectra=<FONT FACE="Symbol">l</FONT>EtOH/max=234nm(conjugated diene)[[Reference:Hamberg_M:,Lipids,1975,10,87|{{RelationTable/GetFirstAuthor|Reference:Hamberg_M:,Lipids,1975,10,87}}]][[Reference:Sessa_DJ:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1977,12,613|{{RelationTable/GetFirstAuthor|Reference:Sessa_DJ:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1977,12,613}}]]
|UV Spectra= lambda EtOH/max=234nm(conjugated diene)[[Reference:Hamberg_M:,Lipids,1975,10,87|{{RelationTable/GetFirstAuthor|Reference:Hamberg_M:,Lipids,1975,10,87}}]][[Reference:Sessa_DJ:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1977,12,613|{{RelationTable/GetFirstAuthor|Reference:Sessa_DJ:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1977,12,613}}]]
|IR Spectra=Methyl ester: trans, trans isomer: trans, trans conjugated dinen(985cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>), free OH(3600cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>), bonded OH(3695-3318cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>); cis, trans isomer: cis, trans conjugated diene(990, 968cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>), olefinic(3005cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>), free OH(3600cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>), bonded OH(3700-3160cm
|IR Spectra=Methyl ester: trans, trans isomer: trans, trans conjugated dinen(985cm^{-1}), free OH(3600cm^{-1}), bonded OH(3695-3318cm^{-1}); cis, trans isomer: cis, trans conjugated diene(990, 968cm^{-1}), olefinic(3005cm^{-1}), free OH(3600cm^{-1}), bonded OH(3700-3160cm^{-1}) [[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}}]][[Reference:Sessa_DJ:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1977,12,613|{{RelationTable/GetFirstAuthor|Reference:Sessa_DJ:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1977,12,613}}]]
|NMR Spectra=<SUP><FONT SIZE=-1>1</FONT></SUP>H-NMR(methyl ester): trans, trans olefinic protons(5.41ppm), cis,trans olefinic protons(5.91ppm), C13(4.15-4.20ppm), C8(2.07-2.10ppm) [[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}}]][[Reference:Sessa_DJ:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1977,12,613|{{RelationTable/GetFirstAuthor|Reference:Sessa_DJ:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1977,12,613}}]]
|NMR Spectra=^1 H-NMR(methyl ester): trans, trans olefinic protons(5.41ppm), cis,trans olefinic protons(5.91ppm), C13(4.15-4.20ppm), C8(2.07-2.10ppm) [[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}}]][[Reference:Sessa_DJ:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1977,12,613|{{RelationTable/GetFirstAuthor|Reference:Sessa_DJ:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1977,12,613}}]]
|Source=Minor degradation products of linoleate hydroperoxide in the presence of Fe(III)-cystein[[Reference:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1974,9,696|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1974,9,696}}]]. A degradation product of hydroperoxymethyllinoleate in the presence of di-t-butyl diperoxyoxalate or Co(II)[[Reference:Yamamoto_Y:Saeki_N:Haga_S:Niki_E:_Kamiya_Y:,Bull. Chem. Soc. Jpn.,1984,57,3177|{{RelationTable/GetFirstAuthor|Reference:Yamamoto_Y:Saeki_N:Haga_S:Niki_E:_Kamiya_Y:,Bull. Chem. Soc. Jpn.,1984,57,3177}}]]. Reaction products between hydroperoxylinoleate and soy bean lipoxygenase[[Reference:Streckert_G:Stan_HJ:,Lipids,1975,10,847|{{RelationTable/GetFirstAuthor|Reference:Streckert_G:Stan_HJ:,Lipids,1975,10,847}}]].
|Chemical Synthesis=
|Metabolism=
|Biological Activity=Trans, trans configuration showed a slightly lower toxicity than linoleate monohydroxyperoxide<!--8045-->[[Reference:Fujimoto_K:,Fragrance J. (in Japanese),1986,76,21|{{RelationTable/GetFirstAuthor|Reference:Fujimoto_K:,Fragrance J. (in Japanese),1986,76,21}}]].
}}
 
{{MassbankSpectra|
UT000037
UT000038
UT000039
UT000040
UT000041
UT000042
UT000043
UT000044
UT000045
}}
}}
{{Lipid/Footer}}

Latest revision as of 00:00, 17 January 2014

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Upper classes: LB LBF



IDs and Links
LipidBank DFA8023
LipidMaps LMFA01050125
CAS
KEGG {{{KEGG}}}
KNApSAcK {{{KNApSAcK}}}
mol LBF18207HO03
13-HODE
LBF18207HO03.png
Structural Information
13-Hydroxy-9,11-octadecadienoic acid
  • 13-HODE
Formula C18H32O3
Exact Mass 296.23514489
Average Mass 296.44488
SMILES CCCCCC(O)C=CC=CCCCCCCCC(O)=O
Physicochemical Information
Minor degradation products of linoleate hydroperoxide in the presence of Fe(III)-cystein Gardner_HW et al.. A degradation product of hydroperoxymethyllinoleate in the presence of di-t-butyl diperoxyoxalate or Co(II) Yamamoto_Y et al.. Reaction products between hydroperoxylinoleate and soy bean lipoxygenase Streckert_G et al..
Trans, trans configuration showed a slightly lower toxicity than linoleate monohydroxyperoxide Fujimoto_K .
Spectral Information
Mass Spectra GC-EI-MS(after methanolysis and trimethylsilylation) Gardner_HW et al. StreckertGet al. KleimanRet al. Frankel_EN et al. Lundberg_WO et al.: m/e=382[M], 367[M-CH3], 351[M-OCH3], 311[M-(CH2)4CH3], 225[M-(CH2)7COOCH3], GC-EI-MS(after methanolysis, hydrogenation and trimethylsilylation) StreckertGet al. HambergM, GC-EI-MS(after methanolysis and hydrogenation) Christophersen_BO
UV Spectra λ EtOH/max=234nm(conjugated diene) HambergM Sessa_DJ et al.
IR Spectra Methyl ester: trans, trans isomer: trans, trans conjugated dinen(985cm-1), free OH(3600cm-1), bonded OH(3695-3318cm-1); cis, trans isomer: cis, trans conjugated diene(990, 968cm-1), olefinic(3005cm-1), free OH(3600cm-1), bonded OH(3700-3160cm-1) Neff_WE et al. Sessa_DJ et al.
NMR Spectra 1H-NMR(methyl ester): trans, trans olefinic protons(5.41ppm), cis,trans olefinic protons(5.91ppm), C13(4.15-4.20ppm), C8(2.07-2.10ppm) Neff_WE et al. Sessa_DJ et al.
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF18207HO03 See above. Christophersen_BO 1968
n.a. LBF18207HO03 See above. Frankel_EN et al. 1977
n.a. LBF18207HO03 See above. Fujimoto_K 1986
n.a. LBF18207HO03 See above. Gardner_HW et al. 1974
n.a. LBF18207HO03 See above. Hamberg_M 1975
n.a. LBF18207HO03 See above. Kleiman_R et al. 1973
n.a. LBF18207HO03 See above. Lundberg_WO et al. 1949
n.a. LBF18207HO03 See above. Neff_WE et al. 1978
n.a. LBF18207HO03 See above. Sessa_DJ et al. 1977
n.a. LBF18207HO03 See above. Streckert_G et al. 1975
n.a. LBF18207HO03 See above. Yamamoto_Y et al. 1984
n.a. LBF18207HO03 See above. Yamamoto_Y et al. 1984



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