Fatty acid

DATA No : DFA8007 INFORMANT : Tetsuyuki Kobayashi

NAME : 9,10-Epoxy-12-Octadecenoic Acid/9,10-Epoxy-12-Octadecenoate

BIOLOGICAL ACTIVITY

Antimicrobial compounds for Piricularia oryzae, a pathogenic fungus of rice blast disease (Imochi-byo)(Ref. 8072)

PHYSICAL AND CHEMICAL PROPERTIES

SPECTRAL DATA

UV SPECTRA	:

IR SPECTRA	:	Olefinic(3002cm^-¹), cis unsaturation(718cm^-¹), cis epoxide(835-815cm^-¹)(Ref. 8017)

NMR SPECTRA	:	¹H-NMR(Ref. 8017): olefinic protons(5.44ppm), isolated cis epoxide(2.92ppm)

MASS SPECTRA	:	GC-EI-MS(Ref. 8017): m/e= 310[M], 279[M-OCH3], 199[M-CH3(CH2)4CH=CHCH2], 153[M-(CH2)7-COOCH3], GC-EI-MS(after solvolysation-trimethylsilylation in MeOH)(Ref. 8062)

OTHER SPECTRA	:

CHROMATOGRAM DATA

SOURCE

In autooxidated methyllinoleate(Ref. 8017). A major secondary product by autooxidation in a lipid film of linoleate(Ref. 8062).

CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

8, 9-; 10, 11- and 11, 12-Epoxide were detected in autooxidated methyl linoleate as well as 9, 10-epoxide(Ref. 8017).

REFERENCES

[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)

[8062]

AUTHOR	:	Wu, G. S., Stein, R. A., and Mead, J. F.
TITLE	:	Autoxidation of fatty acid monolayers adsorbed on silica gel: II. Rates and products PubMed ID:200817
JOURNAL	:	Lipids.
VOL	:	12 PAGE : 971-978 (1977)

[8072]

AUTHOR	:	Kato, T., Yamaguthi, H., Uehara, T., and Namai, T.
TITLE	:	Tolerance to Race blast and Oxidized Unsaturated Fatty Acids
JOURNAL	:	Chemistry and Biology (in Japanese)
VOL	:	24 PAGE : 183 -188 (1986)