LBF18206HP01

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(脂肪酸)
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Upper classes: LB LBF



9-HPODE
LBF18206HP01.png
Structural Information
Systematic Name 9-Hydroperoxy-10,12-octadecadienoic acid
Common Name
  • 9-HPODE
Symbol
Formula C18H32O4
Exact Mass 312.23005951199997
Average Mass 312.44428
SMILES CCCCCC=CC=CC(OO)CCCCCCCC(O)=O
Physicochemical Information
Melting Point
Boiling Point
Density
Optical Rotation
Refractive Index
Solubility
Source Auto oxidation of methyllinoleate Frankel_EN Frankel_EN Frankel_EN Frankel_EN Chan_HWS et al.. Oxidation of methyl linoleate by singlet oxygen Frankel_EN Frankel_EN Frankel_EN Frankel_EN . Oxidation of linoleic acid by lipoxygenase Mathuo_M Wakabayashi_T . Production mechanism (auto oxidation): bis-allylic hydrogen at C11.
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
Genetic Information
Note
Spectral Information
Mass Spectra GC/EI-MS(after methanolysis, reduction and trimethylsilylation) Frankel_EN et al. KleimanRet al. Gardner_HW et al. Frankel_EN et al. HambergM: m/e= 382[M], 292[M-HOTMS], 311[M-(CH2)4CH3], 225[M-(CH2)7COOCH3] standard peak/ GC-EI-MS(after methylation, reduction and hydrogenation) Chan_HWS DolevAet al. Zimmerman_DC et al.: m/e= 187[CH(OH)(CH2)7COOCH3], 158[(CH2)7COOCH3+H], 155[C(OH)-(CH)7CO]
UV Spectra Trans, cis isomer: λ max=236nm, ε =25900, trans, trans isomer: λ max=233nm, ε =28600 Chan_HW et al. Bolland_JL et al. Lundberg_WO et al. Lundberg_WO et al. Gardner_HW et al. Gardner_HW et al.
IR Spectra Methyl ester: Chan_HW et al. Gardner_HW et al. Cannon_JA et al. Privett_OS et al. Sephton_HH et al. Graveland_A_ Privett_OS et al. Gardner_HW et al.: trans, cis isomer: 986 and 949cm-1, trans, trans isomer: 989cm-1, OOH group: 3550cm-1
NMR Spectra 1H-NMR Chan_HW et al. Frankel_EN et al., 1H-NMR( after methanolyzation and reduction) Gardner_HW et al. Neff_WE et al.: trans,cis isomer: C10-13 (5.42-6.48ppm), C14 (2.10-2.18ppm), C9(4.15ppm), J10-11= 15.4Hz(trans), J12-13= 10.8Hz (cis), trans, trans isomer: olefinic protons (5.41ppm), C14 (2.07ppm), C9 (4.20ppm)
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF18206HP01 See above. Bolland_JL et al. 1945
n.a. LBF18206HP01 See above. Cannon_JA et al. 1952
n.a. LBF18206HP01 See above. Chan_HW et al. 1977
n.a. LBF18206HP01 See above. Chan_HWS 1977
n.a. LBF18206HP01 See above. Chan_HWS et al. 1982
n.a. LBF18206HP01 See above. Dolev_A et al. 1967
n.a. LBF18206HP01 See above. Frankel_EN 1987
n.a. LBF18206HP01 See above. Frankel_EN 1980
n.a. LBF18206HP01 See above. Frankel_EN 1983
n.a. LBF18206HP01 See above. Frankel_EN 1984
n.a. LBF18206HP01 See above. Frankel_EN et al. 1979
n.a. LBF18206HP01 See above. Frankel_EN et al. 1977
n.a. LBF18206HP01 See above. Fujimoto_K 1986
n.a. LBF18206HP01 See above. Gardner_HW et al. 1974
n.a. LBF18206HP01 See above. Gardner_HW et al. 1970
n.a. LBF18206HP01 See above. Gardner_HW et al. 1972
n.a. LBF18206HP01 See above. Graveland_A_ 1970
n.a. LBF18206HP01 See above. Hamberg_M 1975
n.a. LBF18206HP01 See above. Kleiman_R et al. 1973
n.a. LBF18206HP01 See above. Logani_MK et al. 1980
n.a. LBF18206HP01 See above. Lundberg_WO et al. 1947
n.a. LBF18206HP01 See above. Lundberg_WO et al. 1949
n.a. LBF18206HP01 See above. Mathuo_M 1986
n.a. LBF18206HP01 See above. Neff_WE et al. 1978
n.a. LBF18206HP01 See above. Privett_OS et al. 1953
n.a. LBF18206HP01 See above. Privett_OS et al. 1955
n.a. LBF18206HP01 See above. Sephton_HH et al. 1956
n.a. LBF18206HP01 See above. Sevanian_A et al. 1985
n.a. LBF18206HP01 See above. Wakabayashi_T 1980
n.a. LBF18206HP01 See above. Zimmerman_DC et al. 1970



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