Fatty acid

DATA No : DFA8012 INFORMANT : Tetsuyuki Kobayashi

NAME : 9,10-Epoxy-13-Hydroxy-11-Octadecenoic Acid/9,10-Epoxy-13-Hydroxy-11-Octadecenoate

COMMON NAME	:
SYMBOL	:
FORMULA	:	C₁₈H₃₂O₄ MOL.WT (average) : 312.444

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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES

MELTING POINT	:

BOILING POINT	:

REFRACTIVE INDEX	:

OPTICAL ROTATION	:

DENSITY	:

SOLUBILITY	:

SPECTRAL DATA

UV SPECTRA	:	l=277 and 316nm(very weak absorption)(Ref. 8009)

IR SPECTRA	:	Metyl ester(Ref. 8017/8056/8009): trans olefin(965-958cm^-¹), trans epoxide(890-874 cm^-¹), cis epoxide(weak absorprion; 845 AND 830cm^-¹), free OH(3600cm^-¹),bonded OH(3640-3380cm^-¹)

NMR SPECTRA	:	¹H-NMR(methyl ester)(Ref. 8017/8056/8009): C9(2.83ppm), C10(3.09-3.1ppm;trans epoxide), C11(5.45-5.53ppm), C12(5.93-5.95ppm), C13(3.9-4.2ppm), C12, 13(2.9-3.4ppm;cis epoxide), OH proton(3.6ppm), J11-12=15.6Hz(trans unsaturation), J9-10=2-2.2Hz(trans epoxide)

MASS SPECTRA	:	GC-EI-MS(after methanolysis and trimethylsilylation)(Ref. 8017/8056/8009/8012): m/e= 398[M], 383[M-CH3], 367[M-OCH3], 327[M-(CH2)4CH3], 241[M-(CH2)7COOCH3]

OTHER SPECTRA	:

CHROMATOGRAM DATA

SOURCE

A degradation product of 13-hydroperoxymethyllinoleate(Ref. 8056/8057). A major compound generated by autooxidation of methyllinoleate[the epoxide ring and double bond show trans configuration](Ref. 8017/8012). Oxidation of linoleic acid by wheat lipoxygenase[the epoxy ring shows cis configuration].

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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[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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[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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[8057]

AUTHOR	:	Schieberle, P., and Grosch, W.
TITLE	:	Decomposition of Linoleic Acid Hydroperoxides II. Breakdown of Methyl 13-Hydroperoxy-cis-9-trans-11-Octadecadienoate by Radicals or Copper II Ions
JOURNAL	:	Z. Lebensm. Unters. Forsch.
VOL	:	173 PAGE : 192 -198 (1981)

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