LBF18207HO03

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Upper classes: LB LBF



13-HODE
LBF18207HO03.png
Structural Information
Systematic Name 13-Hydroxy-9,11-octadecadienoic acid
Common Name
  • 13-HODE
Symbol
Formula C18H32O3
Exact Mass 296.23514489
Average Mass 296.44488
SMILES CCCCCC(O)C=CC=CCCCCCCCC(O)=O
Physicochemical Information
Melting Point
Boiling Point
Density
Optical Rotation
Refractive Index
Solubility
Source 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..
Chemical Synthesis
Metabolism
Biological Activity Trans, trans configuration showed a slightly lower toxicity than linoleate monohydroxyperoxide Fujimoto_K .
Genetic Information
Note
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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