LBF18108HO04: Difference between revisions

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


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|LipidBank=DFA8032
|LipidBank=DFA8032
|LipidMaps=LMFA01050134
|LipidMaps=LMFA01050134
|SysName=9,12,13-Trihydroxy-10-Octadecenoic Acid
|SysName=9,12,13-Trihydroxy-10-octadecenoic acid
|Common Name=&&9,12,13-Trihydroxy-10-Octadecenoic Acid&&9,12,13-Trihydroxy-10-Octadecenoate&&
|Common Name=&&9,12,13-Trihydroxy-10-octadecenoic acid&&
|Mass Spectra=GC-EI-MS(after methanolysis and trimethylsilylation)[[Reference:Streckert_G:Stan_HJ:,Lipids,1975,10,847|{{RelationTable/GetFirstAuthor|Reference:Streckert_G:Stan_HJ:,Lipids,1975,10,847}}]][[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:Schieberle_P:Tsoukalas_B:Grosch_W:,Z. Lebensm. Unters. Forsch.,1979,168,448|{{RelationTable/GetFirstAuthor|Reference:Schieberle_P:Tsoukalas_B:Grosch_W:,Z. Lebensm. Unters. Forsch.,1979,168,448}}]][[Reference:Gardner_HW:Nelson_EC:Tjarks_LW:England_RE:,Chem. Phys. Lipids,1984,35,87|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Nelson_EC:Tjarks_LW:England_RE:,Chem. Phys. Lipids,1984,35,87}}]][[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:Galliard_T:Phillips_DR:Matthew_JA:,Biochim. Biophys. Acta,1975,409,157|{{RelationTable/GetFirstAuthor|Reference:Galliard_T:Phillips_DR:Matthew_JA:,Biochim. Biophys. Acta,1975,409,157}}]][[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}}]]: m/e=545[M-CH3], 529[M-OCH3], 460[rearrangment peak], 259[SMTO=CH-(CH2)7COOCH3], 173[SMTO=CH-(CH2)4CH3], 387[M-173], 301[M-259], 298[M-HOTMS], GC-EI-MS(after methanolysis, trimethylsilylation and isopropylidene treatment), GC-EI-MS(after methanolysis, hydrogenation and trimethylsilylation)
|Mass Spectra=GC-EI-MS(after methanolysis and trimethylsilylation)[[Reference:Streckert_G:Stan_HJ:,Lipids,1975,10,847|{{RelationTable/GetFirstAuthor|Reference:Streckert_G:Stan_HJ:,Lipids,1975,10,847}}]][[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:Schieberle_P:Tsoukalas_B:Grosch_W:,Z. Lebensm. Unters. Forsch.,1979,168,448|{{RelationTable/GetFirstAuthor|Reference:Schieberle_P:Tsoukalas_B:Grosch_W:,Z. Lebensm. Unters. Forsch.,1979,168,448}}]][[Reference:Gardner_HW:Nelson_EC:Tjarks_LW:England_RE:,Chem. Phys. Lipids,1984,35,87|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Nelson_EC:Tjarks_LW:England_RE:,Chem. Phys. Lipids,1984,35,87}}]][[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:Galliard_T:Phillips_DR:Matthew_JA:,Biochim. Biophys. Acta,1975,409,157|{{RelationTable/GetFirstAuthor|Reference:Galliard_T:Phillips_DR:Matthew_JA:,Biochim. Biophys. Acta,1975,409,157}}]][[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}}]]: m/e=545[M-CH3], 529[M-OCH3], 460[rearrangment peak], 259[SMTO=CH-(CH2)7COOCH3], 173[SMTO=CH-(CH2)4CH3], 387[M-173], 301[M-259], 298[M-HOTMS], GC-EI-MS(after methanolysis, trimethylsilylation and isopropylidene treatment), GC-EI-MS(after methanolysis, hydrogenation and trimethylsilylation)
|IR Spectra=Methyl ester: olefinic trans unsaturation(990-965 cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>), free OH(3620-3595 cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>), bonded OH(3640-3160cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>)[[Reference:Streckert_G:Stan_HJ:,Lipids,1975,10,847|{{RelationTable/GetFirstAuthor|Reference:Streckert_G:Stan_HJ:,Lipids,1975,10,847}}]][[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:Schieberle_P:Tsoukalas_B:Grosch_W:,Z. Lebensm. Unters. Forsch.,1979,168,448|{{RelationTable/GetFirstAuthor|Reference:Schieberle_P:Tsoukalas_B:Grosch_W:,Z. Lebensm. Unters. Forsch.,1979,168,448}}]][[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: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: olefinic trans unsaturation(990-965 cm^{-1}), free OH(3620-3595 cm^{-1}), bonded OH(3640-3160cm^{-1})[[Reference:Streckert_G:Stan_HJ:,Lipids,1975,10,847|{{RelationTable/GetFirstAuthor|Reference:Streckert_G:Stan_HJ:,Lipids,1975,10,847}}]][[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:Schieberle_P:Tsoukalas_B:Grosch_W:,Z. Lebensm. Unters. Forsch.,1979,168,448|{{RelationTable/GetFirstAuthor|Reference:Schieberle_P:Tsoukalas_B:Grosch_W:,Z. Lebensm. Unters. Forsch.,1979,168,448}}]][[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: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)[[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:Gardner_HW:Nelson_EC:Tjarks_LW:England_RE:,Chem. Phys. Lipids,1984,35,87|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Nelson_EC:Tjarks_LW:England_RE:,Chem. Phys. Lipids,1984,35,87}}]][[Reference:Graveland_A_:,J. Am. Oil Chem. Soc.,1970,47,352|{{RelationTable/GetFirstAuthor|Reference:Graveland_A_:,J. Am. Oil Chem. Soc.,1970,47,352}}]]:olefinic protons(5.74-5.86ppm), C9, 12(3.7-4.2ppm), C13(3.2-3.77ppm), OH(3.6ppm)
|NMR Spectra=^1 H-NMR(methyl ester)[[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:Gardner_HW:Nelson_EC:Tjarks_LW:England_RE:,Chem. Phys. Lipids,1984,35,87|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Nelson_EC:Tjarks_LW:England_RE:,Chem. Phys. Lipids,1984,35,87}}]][[Reference:Graveland_A_:,J. Am. Oil Chem. Soc.,1970,47,352|{{RelationTable/GetFirstAuthor|Reference:Graveland_A_:,J. Am. Oil Chem. Soc.,1970,47,352}}]]:olefinic protons(5.74-5.86ppm), C9, 12(3.7-4.2ppm), C13(3.2-3.77ppm), OH(3.6ppm)
|NOTE Spectra=ODR analysis [[Reference:Gardner_HW:Nelson_EC:Tjarks_LW:England_RE:,Chem. Phys. Lipids,1984,35,87|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Nelson_EC:Tjarks_LW:England_RE:,Chem. Phys. Lipids,1984,35,87}}]]
|NOTE Spectra=ODR analysis [[Reference:Gardner_HW:Nelson_EC:Tjarks_LW:England_RE:,Chem. Phys. Lipids,1984,35,87|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Nelson_EC:Tjarks_LW:England_RE:,Chem. Phys. Lipids,1984,35,87}}]]
|Source=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}}]] or potato extracts[[Reference:Galliard_T:Phillips_DR:Matthew_JA:,Biochim. Biophys. Acta,1975,409,157|{{RelationTable/GetFirstAuthor|Reference:Galliard_T:Phillips_DR:Matthew_JA:,Biochim. Biophys. Acta,1975,409,157}}]]. Major reactive products between 13-hydroperoxylinoleate and hemathin[[Reference:Dix_TA:Marnett_LJ:,J. Am. Chem. Soc.,1983,105,7001|{{RelationTable/GetFirstAuthor|Reference:Dix_TA:Marnett_LJ:,J. Am. Chem. Soc.,1983,105,7001}}]]. Oxidative products of 13-hydroperoxylinoleate[[Reference:Gardner_HW:Nelson_EC:Tjarks_LW:England_RE:,Chem. Phys. Lipids,1984,35,87|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Nelson_EC:Tjarks_LW:England_RE:,Chem. Phys. Lipids,1984,35,87}}]]. A degradation product of 13-hydroperoxylinoleate 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}}]].
|Chemical Synthesis=
|Metabolism=
|Biological Activity=It showed a toxicity corresponding to 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}}]].
|Other Spectra=ODR analysis [[Reference:Gardner_HW:Nelson_EC:Tjarks_LW:England_RE:,Chem. Phys. Lipids,1984,35,87|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Nelson_EC:Tjarks_LW:England_RE:,Chem. Phys. Lipids,1984,35,87}}]]
}}
}}
{{Lipid/Footer}}

Latest revision as of 06:35, 26 May 2010

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Upper classes: LB LBF



9,12,13-Trihydroxy-10-octadecenoic acid
LBF18108HO04.png
Structural Information
9,12,13-Trihydroxy-10-octadecenoic acid
  • 9,12,13-Trihydroxy-10-octadecenoic acid
Formula C18H34O5
Exact Mass 330.240624198
Average Mass 330.45956
SMILES CCCCCC(O)C(O)C=CC(O)CCCCCCCC(O)=O
Physicochemical Information
Reaction products between hydroperoxylinoleate and soy bean lipoxygenase Streckert_G et al. or potato extracts Galliard_T et al.. Major reactive products between 13-hydroperoxylinoleate and hemathin Dix_TA et al.. Oxidative products of 13-hydroperoxylinoleate Gardner_HW et al.. A degradation product of 13-hydroperoxylinoleate in the presence of Fe(III)-cystein Gardner_HW et al..
It showed a toxicity corresponding to linoleate monohydroxyperoxide Fujimoto_K .
Spectral Information
Mass Spectra GC-EI-MS(after methanolysis and trimethylsilylation) StreckertGet al. Neff_WE et al. SchieberlePet al. Gardner_HW et al. Graveland_A_ GalliardTet al. Frankel_EN et al.: m/e=545[M-CH3], 529[M-OCH3], 460[rearrangment peak], 259[SMTO=CH-(CH2)7COOCH3], 173[SMTO=CH-(CH2)4CH3], 387[M-173], 301[M-259], 298[M-HOTMS], GC-EI-MS(after methanolysis, trimethylsilylation and isopropylidene treatment), GC-EI-MS(after methanolysis, hydrogenation and trimethylsilylation)
UV Spectra
IR Spectra Methyl ester: olefinic trans unsaturation(990-965 cm-1), free OH(3620-3595 cm-1), bonded OH(3640-3160cm-1) StreckertGet al. Neff_WE et al. SchieberlePet al. Graveland_A_ Sessa_DJ et al.
NMR Spectra 1H-NMR(methyl ester) Neff_WE et al. Gardner_HW et al. Graveland_A_ :olefinic protons(5.74-5.86ppm), C9, 12(3.7-4.2ppm), C13(3.2-3.77ppm), OH(3.6ppm)
Other Spectra ODR analysis Gardner_HW et al.
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF18108HO04 See above. Dix_TA et al. 1983
n.a. LBF18108HO04 See above. Frankel_EN et al. 1977
n.a. LBF18108HO04 See above. Fujimoto_K 1986
n.a. LBF18108HO04 See above. Galliard_T et al. 1975
n.a. LBF18108HO04 See above. Gardner_HW et al. 1984
n.a. LBF18108HO04 See above. Graveland_A_ 1970
n.a. LBF18108HO04 See above. Neff_WE et al. 1978
n.a. LBF18108HO04 See above. Schieberle_P et al. 1979
n.a. LBF18108HO04 See above. Streckert_G et al. 1975