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Fatty acid
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Upper classes: LB LBF

Structural Information
Systematic Name 13-Hydroxy-9,11-octadecadienoic acid
Common Name
  • 13-HODE
Formula C18H32O3
Exact Mass 296.23514489
Average Mass 296.44488
Physicochemical Information
Melting Point
Boiling Point
Optical Rotation
Refractive Index
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
Biological Activity Trans, trans configuration showed a slightly lower toxicity than linoleate monohydroxyperoxide Fujimoto_K .
Genetic Information
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
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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