LBF18303HP06

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Upper classes: LB LBF

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LipidBank
DFA8063
LipidMaps
LMFA01040047
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KNApSAcK
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LBF18303HP06.mol

Methyl-10,12-dihydroperoxy- (8E,13E,15Z) -octadecatrienoic acid
Structural Information
Systematic Name	Methyl-10,12-dihydroperoxy- (trans-8,trans-13,cis-15) -octadecatrienoic acid
Common Name	Methyl-10,12-dihydroperoxy- (8E,13E,15Z) -octadecatrienoic acid
Symbol
Formula	C19H32O6
Exact Mass	356.219888756
Average Mass	356.45378
SMILES	CCC=CC=CC(OO)CC(OO)C=CCCCCCCC(=O)OC
Physicochemical Information
Melting Point
Boiling Point
Density
Optical Rotation
Refractive Index
Solubility
Source	It is produced from 10- or 12-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=468[M]; 453[M-OCH3]; 437[M-OC H3]; 378[M-HOTMS]; 271[SMTO=CHCH=CH(CH2)6COOCH3]; 183[SMTO=CHCH=CHCH=CHCH2 CH3]; CI-MS(110) m/e=339[M+H-H20]; 323[M-OOH]; 305[323-H20]; 199[CHOCH=CH(CH2)6COOCH3+H]
UV Spectra	Conjugated diene: λ max=231-233nm Neff_WE et al.
IR Spectra	OOH group: 3700-3140cm-1[bonded], 3520-3510cm-1[free]; conjugated trans, cis diene: 985-979cm-1, 953-935cm-1; isolated trans unsaturation: 968-960cm-1 Neff_WE et al.
NMR Spectra	1H-NMR Neff_WE et al.: C2, 7, 11, 17: 1.8-2.5ppm; C8, 9, 13, 15, 16: 5.3-6.1ppm; C10, 12: 4.49- 4.51ppm; C14: 6.60-6.63ppm; C18: 1.01-1.10ppm; OOH: 8.02-8.05ppm
Other Spectra
Chromatograms

Reported Metabolites, References
Biospecies ID Compound Name Reference Comment n.a. LBF18303HP06 See above. Frankel_EN 1984 n.a. LBF18303HP06 See above. Fujimoto_K et al. 1984 n.a. LBF18303HP06 See above. Neff_WE et al. 1984 n.a. LBF18303HP06 See above. Neff_WE et al. 1982