LBF20503HP05

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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	DFA8098
LipidMaps	LMFA03070015
CAS
KEGG	{{{KEGG}}}
KNApSAcK	{{{KNApSAcK}}}
mol	LBF20503HP05

Methyl-8-hydroperoxy-5,9,11,14,17-eicosapentaenic acid
Structural Information
Systematic Name	Methyl-8-hydroperoxy-5,9,11,14,17-eicosapentaenic acid
Common Name	Methyl-8-hydroperoxy-5,9,11,14,17-eicosapentaenic acid
Symbol
Formula	C21H32O4
Exact Mass	348.23005951199997
Average Mass	348.47637999999995
SMILES	C(CC=CCC=CC=CC(OO)CC=CCCCC(OC)=O)=CCC
Physicochemical Information
Melting Point
Boiling Point
Density
Optical Rotation
Refractive Index
Solubility
Source	Autooxidation of icosapentaenoate Yamauchi_R et al.. Oxidation of icosapentaenoate by singlet-oxygen Yamauchi_R et al.. Oxidation of icosapentaenoate in the presence of myoglobin.
Chemical Synthesis
Metabolism
Biological Activity
Genetic Information
Note	Isomerization of hydroperoxides generated from icosapentaenoete by autooxidation: the proportion of 5-, 18-isomer (outer hydroperoxides) is higher than that of other isomer (8-,9-,11-,12-,14-,15-isomer[inner hydroperoxides]).
Spectral Information
Mass Spectra	GC-EI-MS(after reduction and TMS-derivatization) YamauchiRet al.: m/e=404[M]; 389[M-CH3] 314[M-HOTMS], GC-EI-MS(Me-ester: after reduction, hydrogenation and TMS-derivatization) YamauchiRet al.: m/e=399[M-CH3]; 383[M-OCH3]; 367[399-CH3OH]; 271[SMTO=CH(CH2)11CH3]
UV Spectra	conjugated diene: λ max=235.5nm YamauchiRet al.
IR Spectra	OOH group: 3400cm-1 YamauchiRet al.
NMR Spectra	1H-NMR YamauchiRet al.: OOH proton: 8.5ppm
Other Spectra
Chromatograms

Reported Metabolites, References
Biospecies ID Compound Name Reference Comment n.a. LBF20503HP05 See above. Yamauchi_R et al. 1983