LBF18304HP03

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Upper classes: LB LBF



Methyl-13,16-dihydroperoxy- (9Z,11E,14E) -octadecatrienoic acid
LBF18304HP03.png
Structural Information
Systematic Name Methyl-13,16-dihydroperoxy- (cis-9,trans-11,trans-14) -octadecatrienoic acid
Common Name
  • Methyl-13,16-dihydroperoxy- (9Z,11E,14E) -octadecatrienoic acid
Symbol
Formula C19H32O6
Exact Mass 356.219888756
Average Mass 356.45378
SMILES COC(=O)CCCCCCCC=CC=CC(OO)C=CC(CC)OO
Physicochemical Information
Melting Point
Boiling Point
Density
Optical Rotation
Refractive Index
Solubility
Source It is produced from a 16-hydroperoxy isomer during autooxidation of linoleate Frankel_EN Frankel_EN Neff_WE et al.. It is produced from 13- or 16-hydroperoxy isomer during oxidation of linoleate by singlet-oxygen Frankel_EN Neff_WE et al. Neff_WE et al..
Chemical Synthesis
Metabolism
Biological Activity It reacts with DNA in the presence of Fe ions and ascorbic acid Fujimoto_K et al..
Genetic Information
Note
Spectral Information
Mass Spectra GC-EI-MS(after reduction and TMS-derivatization) Neff_WE et al.: m/e=453[M-CH3]; 439[M -CH2CH3]; 437[M-OCH3]; 378[M-HOTMS]; 143[(CH2)6C00CH3], GC-EI-MS(after reduction, hydrogenation and TMS-derivatization)(102) m/e=443[M-OCH3]; 315[SMTO=CH(CH2)11COOCH3]
UV Spectra Conjugated diene: λ max=233-235nm Neff_WE et al. Neff_WE et al.
IR Spectra OOH group: 3712-3140cm-1[bonded], 3530-3510cm-1[free]; olefinic protons: 3005cm-1; conjugated cis, trans diene: 988-979cm-1, 953-935cm-1; isolated trans unsaturation: 968-960cm-1 Neff_WE et al. Neff_WE et al.
NMR Spectra 1H-NMR Neff_WE et al. Neff_WE et al.: C2: 2.3ppm; C8, 17: 1.8-2.2ppm; C9, 10, 11, 12, 14, 15: 5.26-6.28ppm, C13, 16: 4.40-4.42ppm; C18: 1.02ppm; OOH: 8.07ppm
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF18304HP03 See above. Frankel_EN 1983
n.a. LBF18304HP03 See above. Frankel_EN 1984
n.a. LBF18304HP03 See above. Fujimoto_K et al. 1984
n.a. LBF18304HP03 See above. Neff_WE et al. 1981
n.a. LBF18304HP03 See above. Neff_WE et al. 1982


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