Fatty acid

DATA No : DFA8046 INFORMANT : Tetsuyuki Kobayashi

NAME : 9-Oxo-10,12-Octadecadienoic Acid/9-Oxo-10,12-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	:	l MeOH /max=277-278nm(e=20300),lmax=267nm(cyclohexane)(Ref. 8013/8059/8056/8071)

IR SPECTRA	:	Trans, trans unsaturations(strong absorption at 1000-990cm^-¹), trans,cis unsaturations(960-955cm^-¹), unsaturated ketone(1695-1600cm^-¹) (Ref. 8013/8059/8056/8071/8069)

NMR SPECTRA	:	¹H-NMR(Ref. 8013/8071): C8(2.54ppm), C10, 12, 13(6.06-6.21ppm), C11(7.02-7.51ppm), C14(2.20-2.23ppm)

MASS SPECTRA	:	GC-EI-MS(after methanolysis and hydrogenation)(Ref. 8056/8071/8012/8069): m/e=308[M], 277[M-OCH3], 237[M-(CH2)4CH3], 185[C(O)(CH2)6COOCH3], 166[CH3(CH2)4-CH=CH-CH=CH-C(OH)=CH2; Maclafferty transposition] 151[M-(CH2)7COOCH3]GC-EI-MS(TMS)(Ref. 8013): m/e=366[M], 341[M-CH3], 295[ [M-(CH2)4CH3], 276[M-HOTMS]

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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[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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