Fatty acid

DATA No : DFA8032 INFORMANT : Tetsuyuki Kobayashi

NAME : 9,12,13-Trihydroxy-10-Octadecenoic Acid/9,12,13-Trihydroxy-10-Octadecenoate

COMMON NAME	:
SYMBOL	:
FORMULA	:	C₁₈H₃₄O₅ MOL.WT (average) : 330.460

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BIOLOGICAL ACTIVITY

It showed a toxicity corresponding to linoleate monohydroxyperoxide(Ref. 8045/8047).

PHYSICAL AND CHEMICAL PROPERTIES

MELTING POINT	:

BOILING POINT	:

REFRACTIVE INDEX	:

OPTICAL ROTATION	:

DENSITY	:

SOLUBILITY	:

SPECTRAL DATA

UV SPECTRA	:

IR SPECTRA	:	Methyl ester: olefinic trans unsaturation(990-965 cm^-¹), free OH(3620-3595 cm^-¹), bonded OH(3640-3160cm^-¹)(Ref. 8059/8017/8056/8009/8071)

NMR SPECTRA	:	¹H-NMR(methyl ester)(Ref. 8017/8069/8009):olefinic protons(5.74-5.86ppm), C9, 12(3.7-4.2ppm), C13(3.2-3.77ppm), OH(3.6ppm)

MASS SPECTRA	:	GC-EI-MS(after methanolysis and trimethylsilylation)(Ref. 8059/8017/8056/8069/8009/8066/8012): m/e=545[M-CH3], 529[M-OCH3], 460[rearrangment peak], 259[SMTO=CH-(CH2)7COOCH3], 173[SMTO=CH-(CH2)4CH3], 387[M-173], 301[M-259], 298[M-HOTMS], GC-EI-MS(after methanolysis, trimethylsilylation and isopropylidene treatment), GC-EI-MS(after methanolysis, hydrogenation and trimethylsilylation)

OTHER SPECTRA	:	ODR analysis (Ref. 8069)

CHROMATOGRAM DATA

SOURCE

Reaction products between hydroperoxylinoleate and soy bean lipoxygenase(Ref. 8059) or potato extracts(Ref. 8066). Major reactive products between 13-hydroperoxylinoleate and hemathin(Ref. 8124). Oxidative products of 13-hydroperoxylinoleate(Ref. 8069). A degradation product of 13-hydroperoxylinoleate in the presence of Fe(III)-cystein(Ref. 8013).

CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES

[8009]

AUTHOR	:	Graceland, A.
TITLE	:	Enzymatic Oxidation of Linoleic Acid and Grycerol-1-monolinoleate in Doughs and Flour-Water Suspensions
JOURNAL	:	J. Am. Oil Chem Soc.
VOL	:	47 PAGE : 352 -361 (1970)

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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)

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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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[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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[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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[8066]

AUTHOR	:	Galliard, T., Phillips, D. R., and Matthew, J. A.
TITLE	:	Enzymic reactions of fatty acid hydroperoxides in extracts of potato tuber. II. Conversion of 9- and 13-hydroperoxy-octadecadienoic acids to monohydroxydienoic acid, epoxyhydroxy- and trihydroxymonoenoic acid derivatives PubMed ID:63
JOURNAL	:	Biochim Biophys Acta.
VOL	:	409 PAGE : 157-171 (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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[8124]

AUTHOR	:	Dix, T. A., and Marnett, I. J.
TITLE	:	Hematin-Catalyzed Rearrangement of Hydroperoxylinoleic Acid to Epoxy Alcohols via An Oxygen Rebound
JOURNAL	:	J. Am. Chem. Soc.
VOL	:	105 PAGE : 7001 -7002 (1983)

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