LBF18110HP01

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Fatty acid (脂肪酸)

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Upper classes: LB LBF

IDs and Links
LipidBank
DFA8068
LipidMaps
LMFA01040052
CAS
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KNApSAcK
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LBF18110HP01.mol

Methyl-10,12,13,15-bisepidioxy-16-hydroperoxy-8-octadecenoate
Structural Information
Systematic Name	Methyl-10,12,13,15-bisepidioxy-16-hydroperoxy-8-octadecenoic acid
Common Name	Methyl-10,12,13,15-bisepidioxy-16-hydroperoxy-8-octadecenoate
Symbol
Formula	C19H32O8
Exact Mass	388.20971799999995
Average Mass	388.45258
SMILES	C(O1)(C(CC)OO)CC(C(O2)CC(C=CCCCCCCC(=O)OC)O2)O1
Physicochemical Information
Melting Point
Boiling Point
Density
Optical Rotation
Refractive Index
Solubility
Source	It is produced from a 10-peroxyradical by singlet-oxygen mediated oxidation of linoleate via succesive 1,3-cyclization Frankel_EN Frankel_EN 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(PH3P) and TMS-derivatization)(105): m/e=313[M-131]; 131[SMTO=CHCH2CH3]; GC-EI-MS(after reduction,hydrogenation, and TMS-derivatization) Neff_WE et al.: m/e=349[SMTO=CHCH2CH(OTMS)CH(OTMS)CH2CH3]; 273[SMTO=CH(CH2)8COOCH3]
UV Spectra
IR Spectra	OOH group: 3700-3150cm-1[bonded], 3530cm-1[free]; isolated trans unsaturation: 960cm-1 Neff_WE et al.
NMR Spectra	1H-NMR Neff_WE et al.: C2: 2.3ppm; C8: 5.35ppm; C9: 5.88ppm; C10, 12, 13, 15: 4.47ppm; C11, 14: 2.1-2.8ppm; C16: 3.88ppm[C15-16 erythro], 4.17ppm[C15-16 threo]; C18: 1.05ppm; OOH: 8.73ppm[C15-16 erythro], 9.20ppm[C15-16 threo] Neff_WE et al.
Other Spectra
Chromatograms

Reported Metabolites, References
Biospecies ID Compound Name Reference Comment n.a. LBF18110HP01 See above. Frankel_EN 1987 n.a. LBF18110HP01 See above. Frankel_EN 1984 n.a. LBF18110HP01 See above. Fujimoto_K et al. 1984 n.a. LBF18110HP01 See above. Neff_WE et al. 1982