LBF18303HP02

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Upper classes: LB LBF



12-Hydroperoxy-9,13,15-octadecatrienoic acid
LBF18303HP02.png
Structural Information
Systematic Name 12-Hydroperoxy-9,13,15-octadecatrienoic acid
Common Name
  • 12-Hydroperoxy-9,13,15-octadecatrienoic acid
Symbol
Formula C18H30O4
Exact Mass 310.21440944799997
Average Mass 310.4284
SMILES CCC=CC=CC(OO)CC=CCCCCCCCC(O)=O
Physicochemical Information
Melting Point
Boiling Point
Density
Optical Rotation
Refractive Index
Solubility
Source Auto oxidation of linoleate Frankel_EN Frankel_EN Frankel_EN Chan_HWS et al.. Oxidation of linoleate by singlet oxygen Frankel_EN Frankel_EN Frankel_EN .
Chemical Synthesis
Metabolism
Biological Activity Pysiological damages are induced by these hydroperoxides which are incorporated into bodies or synthesized endogenously. Logani_MK et al. Sevanian_A et al. Fujimoto_K . It reacts with DNA in the presence of Fe ions and ascorbic acid Fujimoto_K et al..
Genetic Information
Note Isomerization of hydroperoxides: Positional isomers at 9, 12, 13, and 16 and their geometric isomers of cis, cis, trans- or cis, trans, trans are formed. The proportion of 9-, 16- isomers is higher than that of 12-, 13- isomers.
Spectral Information
Mass Spectra EI-MS(Me-ester; after reduction and hydrogenation) Chan_HWS Chan_HWS et al.: m/e=229[O=CH(CH2)10C(=OH)OCH3]; 200[CH2(CH2)9C(=OH)OCH3]; 197[O=CH(CH2)10C=O], GC-EI-MS(Me-ester; after reduction and TMS) TeraoJet al. Frankel_EN et al.: m/e=380[M]; 365[M-CH3]; 183[SMTO=CH-CH=CH-CH=CH-CH2-CH3]
UV Spectra (Me-ester;after reduction;in ethanol) Chan_HWS et al., cis, trans, cis isomer: λ max=233nm , cis, trans, trans isomer: λ max=232nm
IR Spectra (Me-ester; after reduction) Chan_HWS et al. Frankel_EN et al., cis, trans,cis isomer: 990-983 and 951-945cm-1; cis, trans, trans isomer: 992-983cm-1, (Me-ester) ToyodaIet al., OOH group: 3400cm-1
NMR Spectra
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF18303HP02 See above. Chan_HWS 1977
n.a. LBF18303HP02 See above. Chan_HWS et al. 1982
n.a. LBF18303HP02 See above. Chan_HWS et al. 1977
n.a. LBF18303HP02 See above. Frankel_EN 1980
n.a. LBF18303HP02 See above. Frankel_EN 1983
n.a. LBF18303HP02 See above. Frankel_EN 1984
n.a. LBF18303HP02 See above. Frankel_EN et al. 1977
n.a. LBF18303HP02 See above. Fujimoto_K 1986
n.a. LBF18303HP02 See above. Fujimoto_K et al. 1984
n.a. LBF18303HP02 See above. Logani_MK et al. 1980
n.a. LBF18303HP02 See above. Sevanian_A et al. 1985
n.a. LBF18303HP02 See above. Terao_J et al. 1977


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