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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)
[TOP]

[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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