LBF18206HP01

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Fatty acid (脂肪酸)

Glycerolipid (グリセロ脂質)

Sphingolipid (スフィンゴ脂質)

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Upper classes: LB LBF

IDs and Links
LipidBank	DFA8001
LipidMaps	LMFA01040004
CAS
KEGG	{{{KEGG}}}
KNApSAcK	{{{KNApSAcK}}}
mol	LBF18206HP01

9-Hydroperoxy-10,12-Octadecadienoic Acid
Structural Information
Systematic Name	9-Hydroperoxy-10,12-Octadecadienoic Acid/9-Hydroperoxy-10,12-Octadecadienoate
Common Name	9-Hydroperoxy-10,12-Octadecadienoic Acid 9-Hydroperoxy-10,12-Octadecadienoate
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
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: l max=236nm, e =25900, trans, trans isomer: l max=233nm, e=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