Fatty acid

DATA No : DFA8011 INFORMANT : Tetsuyuki Kobayashi

NAME : 9,10-Epoxy-11-Hydroxy-12-Octadecenoic Acid/9,10-Epoxy-11-Hydroxy-12- 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	:

IR SPECTRA	:	Methyl ester(Ref. 8013/8057/8059/8066/8071): trans olefin(980cm^-¹), trans epoxide(900-890cm^-¹), OH(3620-3300cm^-¹)

NMR SPECTRA	:	¹H-NMR(Ref. 8013): trans-epoxy-cis-ene: C9(2.98ppm), C10(2.77ppm), C11(4.63ppm), C12(5.32ppm), C13(5.60ppm), C14(2.06ppm), J9-10=2Hz, J10-11=4Hz, J11-12=8Hz J12-13=11Hz / trans-epoxy-trans-ene: C9(2.93ppm), C10(2.77ppm), C11(4.25ppm), C12, 13(5.54ppm), C14(2.06ppm)

MASS SPECTRA	:	GC-EI-MS(after methanolysis and trimethylsilylation)(Ref. 8013/8059/8012/8063/8071/8017): m/e= 398[M], 383[M-CH3], 241[M-(CH2)7COOCH3], 199[SMTO=CH-CH=CH(CH2)4CH3 or CH(-O-)-CH(CH2)7COOCH3], GC-EI-MS(after methanolysis, reduction and hydrogenation)(078), GC-EI-MS(after aceto-hydrolyzation, methanolysis and trimethylsilylation)(Ref. 8066/8059): m/e=361[SMTO

OTHER SPECTRA	:

CHROMATOGRAM DATA

SOURCE

A minor component of epoxy-hydroxy compounds generated from linoleic acid by autooxidation [the epoxy ring shows trans configuration](Ref. 8017/8012). Soy bean lipoxygenase-catalyzed degradation products of linoleate hydroperoxide(Ref. 8059). A degradation product of 9-hydroperoxylinoleate in the presence of Fe(III)-cystein.

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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[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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[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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[8063]

AUTHOR	:	Gardner, H. W., and Kleiman, R.
TITLE	:	Degradation of linoleic acid hydroperoxides by a cysteine. FeCl3 catalyst as a model for similar biochemical reactions. II. Specificity in formation of fatty acid epoxides PubMed ID:7284409
JOURNAL	:	Biochim Biophys Acta.
VOL	:	665 PAGE : 113-124 (1981)

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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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[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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