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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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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.