LBF18302HP02

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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	DFA8064
LipidMaps	LMFA01040048
CAS
KEGG	{{{KEGG}}}
KNApSAcK	{{{KNApSAcK}}}
mol	LBF18302HP02

Methyl-13,15-Dihydroperoxy-9,11,16-Octadecatrienoate
Structural Information
Systematic Name	Methyl-13,15-Dihydroperoxy-9,11,16-Octadecatrienoate
Common Name	Methyl-13,15-Dihydroperoxy-9,11,16-Octadecatrienoate
Symbol
Formula	C19H32O6
Exact Mass	356.219888756
Average Mass	356.45378
SMILES	CC=CC(OO)CC(OO)C=CC=CCCCCCCCC(=O)OC
Physicochemical Information
Melting Point
Boiling Point
Density
Optical Rotation
Refractive Index
Solubility
Source	It is produced from 13- or 15-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-OCH3]; 378[M-HOTMS]; 311[SMTO=CHCH=CHCH=CH(CH2)7COOCH3]; 143[SMTO=CHCH=CHCH3]
UV Spectra	Conjugated diene: λ max=234-235nm Neff_WE et al.
IR Spectra	OOH group: 3700-3140cm-1[bonded], 3520-3510cm-1[free]; conjugated cis, trans 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: 2.31-2.32ppm; C8, 14: 1.8-2.2ppm; C9, 10, 12, 16, 17: 5.25-6.20ppm; C11: 6.63ppm; C13, 15: 4.48-4.50ppm; C18: 1.8ppm; OOH: 7.94-8.08ppm Neff_WE et al.
Other Spectra
Chromatograms

Reported Metabolites, References
Biospecies ID Compound Name Reference Comment n.a. LBF18302HP02 See above. Frankel_EN 1984 n.a. LBF18302HP02 See above. Fujimoto_K et al. 1984 n.a. LBF18302HP02 See above. Neff_WE et al. 1982