Fatty acid

DATA No : DFA8005 INFORMANT : Tetsuyuki Kobayashi

NAME : 8-Hydroperoxy-9,12-Octadecadienoic Acid

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	:

NMR SPECTRA	:	¹H-NMR (after methanolyzation, reduction and 400MHz )(Ref. 8050): olefinic protons(5.91-5.51ppm), C8 (4.45ppm), C11(2.84ppm), C14(2.05ppm),J9-10= J12-13= 10.7Å }0.2Hz (cis)

MASS SPECTRA	:	GC-EI-MS(after methanolysis, reduction and trimethylsilylation) (Ref. 8050>: m/e= 292[M-HOTMS], 271[CH=CH-CH(OTMS)-(CH2)6COOCH3], 239[M-(CH2)6C00CH3], 173[SMTO=CH-(CH2)6COOCH3-TMS+H], 149[239-HOTMS] standard peak

OTHER SPECTRA	:

CHROMATOGRAM DATA

SOURCE

A minor component of monohydroperoxide generated from linoleic acid or methyllinoleate by autooxidation(Ref. 8050/8051). A minor component of hydroperoxide generated from linoleic acid through oxidation by soy bean lipoxygenase (type-2)(Ref. 8050).

CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

8-OOH and 14-OOH are known as small amount components of monohydroperoxidate from auto oxidation of linoleic acid and oxidation of soybean lipoxygenase(type-2). Their amount does not change by temperature or addition of a-tocopherol(Ref. 8050).

REFERENCES

[8050]

AUTHOR	:	Haslbeck, F., Grosch, W., and Firl, J.
TITLE	:	Formation of hydroperoxides with unconjugated diene systems during autoxidation and enzymic oxygenation of linoleic acid PubMed ID:6402025
JOURNAL	:	Biochim Biophys Acta.
VOL	:	750 PAGE : 185-193 (1983)

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[8051]

AUTHOR	:	Haslbeck, F., and Grosch, W.
TITLE	:	Autoxidation of Phenyl Linoleate and Phenyl Oleate: HPLC Analysis of The Major and Minor Monohydroperoxides as Phenyl Hydroxystearates
JOURNAL	:	Lipids
VOL	:	18 PAGE : 706 -713 (1983)

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