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Fatty acid


DATA No : DFA8023 INFORMANT : Tetsuyuki Kobayashi

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

COMMON NAME:
SYMBOL:
FORMULA: C18H32O3 MOL.WT (average) : 296.445


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BIOLOGICAL ACTIVITY
Trans, trans configuration 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:lEtOH/max=234nm(conjugated diene)(Ref. 8014/8071)

IR SPECTRA:Methyl ester: trans, trans isomer: trans, trans conjugated dinen(985cm-1), free OH(3600cm-1), bonded OH(3695-3318cm-1); cis, trans isomer: cis, trans conjugated diene(990, 968cm-1), olefinic(3005cm-1), free OH(3600cm-1), bonded OH(3700-3160cm

NMR SPECTRA:1H-NMR(methyl ester): trans, trans olefinic protons(5.41ppm), cis,trans olefinic protons(5.91ppm), C13(4.15-4.20ppm), C8(2.07-2.10ppm) (Ref. 8017/8071)

MASS SPECTRA:GC-EI-MS(after methanolysis and trimethylsilylation)(Ref. 8013/8059/8018/8012/8004): m/e=382[M], 367[M-CH3], 351[M-OCH3], 311[M-(CH2)4CH3], 225[M-(CH2)7COOCH3], GC-EI-MS(after methanolysis, hydrogenation and trimethylsilylation)(Ref. 8059/8014), GC-EI-MS(after methanolysis and hydrogenation) (Ref. 8064)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Minor degradation products of linoleate hydroperoxide in the presence of Fe(III)-cystein(Ref. 8013). A degradation product of hydroperoxymethyllinoleate in the presence of di-t-butyl diperoxyoxalate or Co(II)(Ref. 8058). Reaction products bstween hydroperoxylinoleate and soy bean lipoxygenase(Ref. 8059).
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[8004]
AUTHOR:Lundberg, W. O., Chipault, J. R., and Hendrickson, N. J.
TITLE:Observation on The Mechanism of The Autoxidation of Methyl Linolate
JOURNAL:J. Am. Cil Chem. Soc.
VOL:26 PAGE : 109 -115 (1949)
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[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)
[TOP]

[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)
[TOP]

[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)
[TOP]

[8017]
AUTHOR:Neff, W. E., Frankel, E. N., Scholfield, C. R., and Wesleder, D.
TITLE:High-Pressure Liquid Chromatgraphy of Autoxidized Lipids: I. Methyl Oleate and Linoleate
JOURNAL:Lipids
VOL:13 PAGE : 415 -421 (1978)
[TOP]

[8018]
AUTHOR:Kleiman, R., and Spencer, G. F.
TITLE:Gas Chromatgrphy-Mass Spectrometry of Methyl Esters of Unsaturated Oxygenated Fatty Acids
JOURNAL:J. Am. Oil Chem Soc.
VOL:50 PAGE : 31 -38 (1973)
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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)
[TOP]

[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)
[TOP]

[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)
[TOP]

[8064]
AUTHOR:Christophersen, B. O.
TITLE:Formation of monohydroxy-polyenic fatty acids from lipid peroxides by a glutathione peroxidase PubMed ID:5680294
JOURNAL:Biochim Biophys Acta.
VOL:164 PAGE : 35-46 (1968)
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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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