LBF18207HP01

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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	DFA8002
LipidMaps	LMFA01040001
CAS
KEGG	{{{KEGG}}}
KNApSAcK	{{{KNApSAcK}}}
mol	LBF18207HP01

13- Hydroperoxy-9,11-Octadecadienoic Acid
Structural Information
Systematic Name	13- Hydroperoxy-9,11-Octadecadienoic Acid/13- Hydroperoxy-9,11-Octadecadienoate
Common Name	13- Hydroperoxy-9,11-Octadecadienoic Acid 13- Hydroperoxy-9,11-Octadecadienoate
Symbol
Formula	C18H32O4
Exact Mass	312.23005951199997
Average Mass	312.44428
SMILES	CCCCCC(OO)C=CC=CCCCCCCCC(O)=O
Physicochemical Information
Melting Point
Boiling Point
Density
Optical Rotation
Refractive Index
Solubility
Source	Auto oxidation of methyl linoleate 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 . 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. Frankel_EN et al. Gardner_HW et al. HambergM: m/e= 382[M], 292[M-HOTMS], 311[M-(CH2)4CH3] standard peak,225[M-(CH2)7COOCH3] / GC-EI-MS(after methylation, reduction and hydrogenation) Chan_HWS DolevAet al. Zimmerman_DC et al.: m/e= 243[CH(OH)(CH2)11COOCH3], 214[(CH2)11COOCH3+H], 211[C(OH(CH2)11CO]
UV Spectra	Trans, cis isomer: l max= 236nm, e= 26000, trans, trans isomer: l max= 233nm, e=28600 (025/027/028/029/036)
IR Spectra	Methyl ester Chan_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.: cis, trans 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.: C9-13 (5.45-6.53ppm), C13 (4.37ppm), J9-10= 11Hz (cis),J11-12=15Hz (trans) /1H-NMR (after methanolyzation and reduction ) Gardner_HW et al. Neff_WE et al.: cis, trans isomer : olefinic protons(5.91ppm), C8 (2.10ppm), C13(4.15ppm), trans, trans isomer: olefinic protons (5.41ppm), C8 (2.07ppm)
Other Spectra
Chromatograms

Reported Metabolites, References

Biospecies ID Compound Name Reference Comment n.a. LBF18207HP01 See above. Cannon_JA et al. 1952 n.a. LBF18207HP01 See above. Chan_HW et al. 1977 n.a. LBF18207HP01 See above. Chan_HWS 1977 n.a. LBF18207HP01 See above. Chan_HWS et al. 1982 n.a. LBF18207HP01 See above. Dolev_A et al. 1967 n.a. LBF18207HP01 See above. Frankel_EN 1987 n.a. LBF18207HP01 See above. Frankel_EN 1980 n.a. LBF18207HP01 See above. Frankel_EN 1983 n.a. LBF18207HP01 See above. Frankel_EN 1984 n.a. LBF18207HP01 See above. Frankel_EN et al. 1979 n.a. LBF18207HP01 See above. Frankel_EN et al. 1977 n.a. LBF18207HP01 See above. Fujimoto_K 1986 n.a. LBF18207HP01 See above. Gardner_HW et al. 1974 n.a. LBF18207HP01 See above. Gardner_HW et al. 1970 n.a. LBF18207HP01 See above. Graveland_A_ 1970 n.a. LBF18207HP01 See above. Hamberg_M 1975 n.a. LBF18207HP01 See above. Kleiman_R et al. 1973 n.a. LBF18207HP01 See above. Logani_MK et al. 1980 n.a. LBF18207HP01 See above. Mathuo_M 1986 n.a. LBF18207HP01 See above. Neff_WE et al. 1978 n.a. LBF18207HP01 See above. Privett_OS et al. 1953 n.a. LBF18207HP01 See above. Privett_OS et al. 1955 n.a. LBF18207HP01 See above. Sephton_HH et al. 1956 n.a. LBF18207HP01 See above. Sevanian_A et al. 1985 n.a. LBF18207HP01 See above. Wakabayashi_T 1980 n.a. LBF18207HP01 See above. Zimmerman_DC et al. 1970