LBF18106EO02

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Upper classes: LB LBF



9,10-Epoxy-11-hydroxy-12-octadecenoic acid
LBF18106EO02.png
Structural Information
Systematic Name 9,10-Epoxy-11-hydroxy-12-octadecenoic acid
Common Name
  • 9,10-Epoxy-11-hydroxy-12-octadecenoic acid
Symbol
Formula C18H32O4
Exact Mass 312.23005951199997
Average Mass 312.44428
SMILES C(C(C(O)C=CCCCCC)1)(CCCCCCCC(O)=O)O1
Physicochemical Information
Melting Point
Boiling Point
Density
Optical Rotation
Refractive Index
Solubility
Source A minor component of epoxy-hydroxy compounds generated from linoleic acid by autooxidation [the epoxy ring shows trans configuration] Neff_WE et al. Frankel_EN et al.. Soy bean lipoxygenase-catalyzed degradation products of linoleate hydroperoxide Streckert_G et al.. A degradation product of 9-hydroperoxylinoleate in the presence of Fe(III)-cystein.
Chemical Synthesis
Metabolism
Biological Activity
Genetic Information
Note
Spectral Information
Mass Spectra GC-EI-MS(after methanolysis and trimethylsilylation) Gardner_HW et al. StreckertGet al. Frankel_EN et al. Gardner_HW et al. Sessa_DJ et al. Neff_WE et al.: m/e= 398[M], 383[M-CH3], 241[M-(CH2)7COOCH3], 199[SMTO=CH-CH=CH(CH2)4CH3 or CH(-O-)-CH(CH2)7COOCH3], GC-EI-MS(after methanolysis, reduction and hydrogenation)(078), GC-EI-MS(after aceto-hydrolyzation, methanolysis and trimethylsilylation) GalliardTet al. StreckertGet al.: m/e=361[SMTO
UV Spectra
IR Spectra Methyl ester Gardner_HW et al. SchieberlePet al. StreckertGet al. GalliardTet al. Sessa_DJ et al.: trans olefin(980cm-1), trans epoxide(900-890cm-1), OH(3620-3300cm-1)
NMR Spectra 1H-NMR Gardner_HW et al.: trans-epoxy-cis-ene: C9(2.98ppm), C10(2.77ppm), C11(4.63ppm), C12(5.32ppm), C13(5.60ppm), C14(2.06ppm), J9-10=2Hz, J10-11=4Hz, J11-12=8Hz J12-13=11Hz / trans-epoxy-trans-ene: C9(2.93ppm), C10(2.77ppm), C11(4.25ppm), C12, 13(5.54ppm), C14(2.06ppm)
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF18106EO02 See above. Frankel_EN et al. 1977
n.a. LBF18106EO02 See above. Galliard_T et al. 1975
n.a. LBF18106EO02 See above. Gardner_HW et al. 1981
n.a. LBF18106EO02 See above. Gardner_HW et al. 1974
n.a. LBF18106EO02 See above. Neff_WE et al. 1978
n.a. LBF18106EO02 See above. Sessa_DJ et al. 1977
n.a. LBF18106EO02 See above. Streckert_G et al. 1975


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