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Fatty acid


DATA No : DFA8047 INFORMANT : Tetsuyuki Kobayashi

NAME : 13-Oxo-9,11-Octadecadienoic Acid/13-Oxo-9,11-Octadecadienoate

COMMON NAME:
SYMBOL:
FORMULA: C18H30O3 MOL.WT (average) : 294.429


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BIOLOGICAL ACTIVITY
It showed a slightly lower toxicity than linoleate monohydroxyperoxide(Ref. 8045/8047).
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:lMeOH/max=277-278nm(e=20300)(Ref. 8013/8059/8056)(038/078/075), l EtOH /max=278nm(Ref. 8013), lmax=267nm(cyclohexane)(Ref. 8071), DNP hydrazone: lCHCl3/max=388, 304, 265nm(Ref. 8075)

IR SPECTRA:Trans, trans unsaturations(strong absorption at 1000-990cm-1), cis, trans unsaturations(960-955cm-1), unsaturated ketone(1695-1600cm-1)(Ref. 8013/8059/8056/8071)

NMR SPECTRA:1H-NMR(Ref. 8013/8071): C8(2.20-2.23ppm), C9, 10, 12(6.06-6.21ppm), C11(7.02-7.51ppm) C14(2.54ppm)

MASS SPECTRA:GC-EI-MS(after methanolysis and trimethylsilylation)(Ref. 8014/8071/8012/8069): m/e=308[M], 277[M-OCH3], 252[M-CH2=C H-CH2CH3], 237[M-(CH2)4CH3], 209[M-C(O)(CH2)4CH3], 151[M-(CH2)7COOCH3], GC-EI-MS(TMS)(Ref. 8013): m/e=366[M], 341[M-CH3], 295[M-(CH2)4CH3], 276[M-HOTMS], 166[M-(CH2)6C(=O)OTMS]; REARRA

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
A degradation product of hydroperoxylinoleate in the presence of Fe(III)-cystein[trans, trans; or trans, cis](Ref. 8013). A degradation product of hydroperoxymethyllinoleate in the presence of di-t-butyl diperoxyoxalate or Co(II)(Ref. 8058).
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[8012]
AUTHOR:Frankel, E. N., Neff, W. E., Rohwedder, W. K., Khambay, B. P., Garwood, R. F., and Weedon, B. C.
TITLE:Analysis of autoxidized fats by gas chromatography-mass spectrometry: II. Methyl linoleate PubMed ID:927043
JOURNAL:Lipids.
VOL:12 PAGE : 908-913 (1977)
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[8013]
AUTHOR:Gardner, H. W., Kleiman, R., and Weisleder, D.
TITLE:Homolytic Decomposition of Linoleic Acid Hydroperoxide: Identification of Fatty Acid Products
JOURNAL:Lipids
VOL:9 PAGE : 696 -706 (1974)
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[8014]
AUTHOR:Hamberg, M.
TITLE:Decomposition of unsaturated fatty acid hydroperoxides by hemoglobin: Structures of major products of 13L-hydroperoxy-9,11-octadecadienoic acid PubMed ID:1167926
JOURNAL:Lipids.
VOL:10 PAGE : 87-92 (1975)
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[8045]
AUTHOR:Miyazawa, Y (1985 ) II Hydroperoxides and Physiological Factor; 1-2: Foods, in Hydroperoxides and Body ( Uthiyama, M., Mathuo, M., and Sagano, M.,eds.), pp98-122, Press Center of Societies, Japan
TITLE:
JOURNAL:
VOL: PAGE : - ()
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[8047]
AUTHOR:Fujimoto, K.
TITLE:Toxicity and Safety of Lipid Peroxidates
JOURNAL:Fragrance J. (in Japanese)
VOL:76 PAGE : 21 -25 (1986)
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[8056]
AUTHOR:Schieberle, P., Tsoukalas, B., and Grosch, W.
TITLE:Decomposition of Linoleic Acid Hydroperoxides by Radicals I. Structures of Products of Methyl 13-Hydroperoxy-cis, trans-9,11-Octadecadienoate
JOURNAL:Z. Lebensm. Unters. Forsch.
VOL:168 PAGE : 448 -456 (1979)
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[8058]
AUTHOR:Yamamoto, Y., Saeki, N., Haga, S., Niki, E., and Kamiya. Y.
TITLE:Oxidation of Lipids. IX. Decomposition of Methyl Linoleate and Methyl Linolenate Hydroperoxydes in Solution
JOURNAL:Bull. Chem. Soc. Jpn.
VOL:57 PAGE : 3177 -3181 (1984)
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[8059]
AUTHOR:Streckert, G., and Stan, H. J.
TITLE:Conversion of linoleic acid hydroperoxide by soybean lipoxygenase in the presence of guaiacol: identification of the reaction products PubMed ID:813080
JOURNAL:Lipids.
VOL:10 PAGE : 847-854 (1975)
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[8069]
AUTHOR:Gardner, H. W., Nelson, E. C., Tjarks, L. W., and England, R. E.
TITLE:Acid-Catalyzed Transformation of 13(S)- Hydroperoxylinoleic Acid into Epoxyhydroxyoctadecenoic and Trihydroxyoctadecenoic Acids
JOURNAL:Chem. Phys. Lipids
VOL:35 PAGE : 87 -101 (1984)
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[8071]
AUTHOR:Sessa, D. J., Gardner, H. W., Kleiman, R., and Weisleder, D.
TITLE:Oxygenated fatty acid constituents of soybean phosphatidylcholines PubMed ID:561287
JOURNAL:Lipids.
VOL:12 PAGE : 613-619 (1977)
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[8075]
AUTHOR:Garssen, G. J., Vliegenthart, J. F., and Boldingh, J.
TITLE:An anaerobic reaction between lipoxygenase, linoleic acid and its hydroperoxides PubMed ID:5165730
JOURNAL:Biochem J.
VOL:122 PAGE : 327-332 (1971)
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