LBF18203HP01

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Upper classes: LB LBF



Methyl-10,12-epidioxy-9-hydroperoxy-13,15-octadecadienoate
LBF18203HP01.png
Structural Information
Systematic Name Methyl-10,12-epidioxy-9-hydroperoxy-13,15-octadecadienoic acid
Common Name
  • Methyl-10,12-epidioxy-9-hydroperoxy-13,15-octadecadienoate
Symbol
Formula C19H32O6
Exact Mass 356.219888756
Average Mass 356.45378
SMILES C(O1)(CC(C=CC=CCC)O1)C(OO)CCCCCCCC(=O)OC
Physicochemical Information
Melting Point
Boiling Point
Density
Optical Rotation
Refractive Index
Solubility
Source Auto oxydation of linoleate Neff_WE et al. Coxon_DT et al.. Oxydation of linoleate in the presence of Fe(III)-ascorbic acid Toyoda_I et al.. Photoenhancemant of linoleate peroxydation[Type II] Neff_WE et al. Neff_WE et al.. Production mechanism Frankel_EN Frankel_EN .
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 Major secondary products of linolenate by autooxidation Frankel_EN Neff_WE et al.. It is formed through 1, 3 cyclization of 12-peroxy radical of linolenate Frankel_EN Frankel_EN Frankel_EN Chan_HWS et al. Coxon_DT et al.. A level of epidioxy hydroperoxides produced by autooxidation of linolenate decreased by supplementation of antioxidants Peers_KE et al..
Spectral Information
Mass Spectra GC-EI-MS(after reduction(PH3P) and TMS) Neff_WE et al.: m/e=397[M-CH3]; 259[SMTO=CH(CH2)7COOCH3]; GC-EI-MS(after reduction with NaBH4 or KI andTMS) Frankel_EN et al.: m/e=259[SMTO=CH(CH2)7COOCH3]; 183[SMTO=CH-CH=CH-CH=CH-CH2CH3]
UV Spectra Conjugated diene: λ max=231-236nm ToyodaIet al. Neff_WE et al. Coxon_DT et al. Neff_WE et al.
IR Spectra OOH group: 3520 cm-1[free], 3700-3100cm-1[bonded]; olefinic protons: 3020-3000cm-1; CONJUGATE TRANS, CIS DIENES: 990-980cm-1, 955-947cm-1 Neff_WE et al. Coxon_DT et al. Neff_WE et al. Neff_WE et al.
NMR Spectra 1H-NMR Neff_WE et al. Neff_WE et al. Coxon_DT et al.: C9: 3.92-4.21; C10: 4.45-4.47; C11: 2.19-2.47, 2.81-2.87; C12: 4.77-4.80; C13: 5.57-5.62; C14: 6.65-6.68; C15: 5.96-6.65; C16: 5.50-5.55; OOH: 9.05-9.56ppm; J13-14=15Hz[C13-14 : trans]; J15-16=10Hz[C15-16: cis]13C-NMR Neff_WE et al. Neff_WE et al.: C9: 86.0; C10, 12: 83.8, 83.0
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF18203HP01 See above. Chan_HWS et al. 1982
n.a. LBF18203HP01 See above. Coxon_DT et al. 1981
n.a. LBF18203HP01 See above. Frankel_EN 1987
n.a. LBF18203HP01 See above. Frankel_EN 1983
n.a. LBF18203HP01 See above. Frankel_EN 1984
n.a. LBF18203HP01 See above. Frankel_EN et al. 1977
n.a. LBF18203HP01 See above. Fujimoto_K et al. 1984
n.a. LBF18203HP01 See above. Neff_WE et al. 1981
n.a. LBF18203HP01 See above. Neff_WE et al. 1982
n.a. LBF18203HP01 See above. Peers_KE et al. 1984
n.a. LBF18203HP01 See above. Toyoda_I et al. 1982


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