LBF18304HP02

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Fatty acid (脂肪酸)

Glycerolipid (グリセロ脂質)

Sphingolipid (スフィンゴ脂質)

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Upper classes: LB LBF

IDs and Links
LipidBank	DFA8061
LipidMaps	LMFA01040045
CAS
KEGG	{{{KEGG}}}
KNApSAcK	{{{KNApSAcK}}}
mol	LBF18304HP02

Methyl-9,16-dihydroperoxy-10,12,14-octadecatrienoic acid
Structural Information
Systematic Name	Methyl-9,16-dihydroperoxy-10,12,14-octadecatrienoic acid
Common Name	Methyl-9,16-dihydroperoxy-10,12,14-octadecatrienoic acid
Symbol
Formula	C19H32O6
Exact Mass	356.219888756
Average Mass	356.45378
SMILES	COC(=O)CCCCCCCC(OO)C=CC=CC=CC(CC)OO
Physicochemical Information
Melting Point
Boiling Point
Density
Optical Rotation
Refractive Index
Solubility
Source	It is produced from 9- or 16-hydroperoxy isomer during autooxidation of linoleate Frankel_EN Frankel_EN Toyoda_I et al. Neff_WE et al.. Oxidation of linoleate in presence of Fe(III)-ascorbic acid Toyoda_I et al.. It is produced from 9- 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., GC-EI-MS(after reduction, hydrogenation and TMS-derivatization) ToyodaIet al. Neff_WE et al., GC-EIMS(after reduction,hydrogenation and TBDMS-derivatization) ToyodaIet al.,CI-MS Frankel_EN et al.
UV Spectra	Conjugated triene: λ max=258-260, 268-269, 278-280nm ToyodaIet al. 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 trans, cis, trans triene: 960cm-1; conjugated trans, trans, trans triene: 996-991cm-1 ToyodaIet al. Neff_WE et al. Neff_WE et al.
NMR Spectra	1H-NMR Neff_WE et al. Neff_WE et al.: C2: 2.30-2.37ppm; C8,17: 1.50-1.85ppm; C9, 16: 4.34-4.42ppm; C10, 11, 12, 13, 14, 15: 5.25-6.90ppm; C18: 0.94-0.95ppm; OOH:7.70-7.94ppm
Other Spectra
Chromatograms

Reported Metabolites, References
Biospecies ID Compound Name Reference Comment n.a. LBF18304HP02 See above. Frankel_EN 1983 n.a. LBF18304HP02 See above. Frankel_EN 1984 n.a. LBF18304HP02 See above. Frankel_EN et al. 1986 n.a. LBF18304HP02 See above. Fujimoto_K et al. 1984 n.a. LBF18304HP02 See above. Neff_WE et al. 1981 n.a. LBF18304HP02 See above. Neff_WE et al. 1982 n.a. LBF18304HP02 See above. Toyoda_I et al. 1982