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Fatty acid


DATA No : DFA8099 INFORMANT : Tetsuyuki Kobayashi

NAME : Methyl 9-Hydroperoxy-5,7,11,14,17-Icosapentaenoate

COMMON NAME:
SYMBOL:
FORMULA: C21H32O4 MOL.WT (average) : 348.476


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:conjugated diene: lmax=235.5nm (Ref. 8109)

IR SPECTRA:OOH group: 3400cm-1 (Ref. 8109)

NMR SPECTRA:1H-NMR(Ref. 8109): OOH proton: 8.5ppm

MASS SPECTRA:GC-EI-MS(after reduction and TMS-derivatization)(Ref. 8109): m/e=404[M]; 389[M-CH3] 314[M-HOTMS], GC-EI-MS(Me-ester: after reduction, hydrogenation and TMS-derivatization) (125): m/e=399[M-CH3]; 383[M-OCH3]; 367[399-CH3OH]

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Autooxidation of icosapentaenoate(Ref. 8109). Oxidation of icosapentaenoate by singlet-oxygen(Ref. 8109). Oxidation of icosapentaenoate in the presence of myoglobin(Ref. 8110).
CHEMICAL SYNTHESIS

METABOLISM

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])(Ref. 8110).
REFERENCES
[8109]
AUTHOR:Yamauchi, R., Yamada, T., Kato, K., and Ueno, Y.
TITLE:Monohydroperoxides Formed by Autoxidation and Photosensitized Oxidation of Methyl Eicosapentaenoate
JOURNAL:Agric. Biol. Chem.
VOL:47 PAGE : 2897 -2902 (1983)
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[8110]
AUTHOR:Yamauchi, R., Yamada, T., Kato, K., and Ueno, Y.
TITLE:Myoglobin-Catalyzed Peroxidation Products of Methyl Eicosapentaenoate
JOURNAL:Agric. Biol. Chem.
VOL:49 PAGE : 3311 -3313 (1985)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.