Fatty acid

DATA No : DFA8022 INFORMANT : Tetsuyuki Kobayashi

NAME : 9-Hydroxy-10,12-Octadecadienoic Acid/9-Hydroxy-10,12-Octadecadienoate

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

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BIOLOGICAL ACTIVITY

Trans, trans isomer 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	:	Methyl ester: l/max=231, 233, 234nm (Ref. 8071)

IR SPECTRA	:	Methyl ester: trans, trans isomer: trans, trans conjugated diene(985cm^-¹), free OH(3600cm^-¹), bonded OH(3695-3318cm^-¹), trans, cis isomer: trans, cis 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), trans,cis olefinic protons(5.91ppm), C9(4.15-4.20ppm), C14(2.07-2.10ppm)(Ref. 8017/8071)

MASS SPECTRA	:	GC-EI-MS(after methanolysis and trimethylsilylation)(Ref. 8059/8018/8012): 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), 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

[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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[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)

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[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)

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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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[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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